Chemfiles 113 Link v1

Aldrich
VOLUME 11 NUMBER 3
2011
Synthetic Reagents
Catalysis
Organometallics
Building Blocks
Specialty Synthesis
Stable Isotopes
Stockroom Reagents
Labware Notes
Potassium carbobenzyloxycyanamide:
an efficient reagent for amine guanylation
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76873
Aldrich
Introduction
Volume 11, Number 3
Sigma-Aldrich Corporation
6000 N. Teutonia Ave.
Milwaukee, WI 53209 USA
Editorial Team
Haydn Boehm, Ph.D.
Wesley Smith
Dean Llanas
Sharbil J. Firsan, Ph.D.
Weimin Qian
Production Team
Cynthia Skaggs
Vincent Clark
Chris Lein
Tom Beckermann
Christian Hagmann
Denise de Voogd
Chemistry Team
Leslie Patterson, Ph.D.
Aaron Thornton, Ph.D.
Daniel Weibel, Ph.D.
Josephine Nakhla, Ph.D.
Ronaldo Mariz, Ph.D.
Pietro Butti, Ph.D.
Mark Redlich, Ph.D.
Troy Ryba, Ph.D.
Todd Halkoski
Paula Freemantle
Mike Willis
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Aldrich ChemFiles (ISSN 19339658) is a publication of Aldrich
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2011 Sigma-Aldrich Co. LLC.
Haydn Boehm, Ph. D.

Global Marketing Manager: Chemical Synthesis
haydn.boehm@sial.com
Dear Fellow Chemists,

Welcome to the third installment of Aldrich ChemFiles for 2011,
our complimentary quarterly innovation newsletter written by
experts from Aldrich Chemistry Product Management and R&D.
Our aim is to keep you informed of the new Aldrich Chemistry products that facilitate the
latest research methodologies and trends, and allow you to access key starting materials
and reagents more efficiently.
As well as introducing all the latest innovations across all of our product lines, in 2011 each
edition of Aldrich ChemFiles is themed to a product line. Aldrich ChemFiles Vol.11, No.3
will focus on our Synthetic Reagents product line. In this issues lead article, TroyRyba,
Product Manager, highlights our new ChiroSolv EnantioPrep Kits which define scalable,
optimized chiral resolution methods, to deliver pure enantiomers within a matter of days.
Our Synthetic Reagents cover molecule is potassium carbobenzyloxycyanamide, which
is an efficient reagent for amine guanylation.
Aldrich ChemFiles Vol. 11, No. 3 will also introduce the latest innovations across all of our
product lines including new chiral catalysts and applications (Catalysis), chiral crotylsilanes
and EZ-CrotylMixes (Organometallics), halogenated pyridines and aldehydes (Building
Blocks), and new ionic liquids (Speciality Synthesis). I would also like to draw attention
to Aldrichs new normality and molarity calculators (acid and base molarity/normality,
mass molarity, and solution dilution) which have been updated on our website at
Aldrich.com/calculator and are now available as iPhone and iPad applications.
We hope that Aldrich ChemFiles will enable you to expand your research toolbox
and advance your chemistry more effectively by implementing the latest innovative
synthetic strategies.
Kind regards,
Dr. Haydn Boehm

Global Marketing Manager: Chemical Synthesis
Table of Contents
Synthetic Reagents. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4
Catalysis. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 12
Organometallics. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 16
Building Blocks. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 18
Specialty Synthesis. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 20
Stable Isotopes. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 22
Stockroom Reagents . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 24
Labware Notes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 26
Synthetic Reagents
Troy Ryba, Ph.D.
Product Manager
troy.ryba@sial.com
Potassium Carbobenzyloxycyanamide:
An Efficient Reagent for Amine Guanylation*
O
O
CN
K
or
Cbz
Me
NH2
Figure 1. Structure of Potassium carbobenzyloxycyanamide.
Eq. 2
NCbz
R2
N
R1
NH2
R1
SiMe3
H2 (1 atm)
Pd/C MeOH
N
H
R2
NCbz
R2
1.1 equiv.
N
R1
NH
R2
N
R1
NH2
NH2
NCbz
Me
N
H
yield (%)
NH2
15 min
85%
15 min
91%
15 min
91%
15 min
88%
15 min
92%
15 min
90%
1h
73%
8h
83%
16 h
73%
16 h
68%
16 h
63%
NCbz
NH2
The reaction of amines with an activated carbodiimide represents

a powerful method for the preparation of guanidines. A simple
and efficient one-pot method for the synthesis of mono-protected
guanidines is presented in Scheme 1. Treatment of this cyanamide with
trimethylsilyl chloride generates a reactive N-silylcarbodiimide capable
of guanylating a variety of amines. Typically the reaction is complete
in 15 minutes for primary and secondary aliphatic amines at room
temperature. Anilines are also reactive but require a little more time. This
method is operationally simple, high yielding at room temperature, and
adequate purification is usually achieved through aqueous acid / base
work up which can remove excess amine or cyanamide, respectively.
TMSCl
CN 1.1 equiv. Cbz
Cbz
N
N
MeCN, rt.
K
N
H
CN
K
time
NCbz
NH2
L499994 potassium salt

carbobenzyloxycyanamide
Eq. 1
product
amine
N
H
NH
NH2
NH
NCbz
N
NH
NCbz
NH
NH2
NH2
NCbz
NH
Me
Me
Me
N
H
NH2
Me
NCbz
Me
Me
Me
NH2
Me
MeO
MeO
NCbz
N
H
NH2
NH2
NH2
NCbz
Scheme 1: Applications of potassium benzyloxycarbonylcyanamide
N
H
NH2
NH2
NCbz
N
H
Me
N
Me
NH2
NCbz
NH2
N
H
NH2
O2N
O2 N
NH2
NCbz
N
H
NH2
--
N.R
Figure 2. Examples of amine guanidinylation with potassium carbobenzyloxycyanamide.

References: Looper, R. E.; Haussener, T. J.; Mack, J. B.C; 2011, submitted.
* Article provided courtesy of Prof. Ryan E. Looper, University of Utah.
Aldrich.com
TO ORDER: Contact your local Sigma-Aldrich office (see back cover), or visit Aldrich.com/chemicalsynthesis.
When you
need a stable
liquid Reductive
Amination Reagent.
CH3
H3C
N
BH3
5-Ethyl-2-methylpyridine borane (PEMB)

725080
Select Substrate Scope

O
R
PEMB, AcOH
R
o
R NH2, 50 C
R
H
R NH2, rt
O
R
PEMB, AcOH
R
R
Examples
Aldehyde
and Amine
Conditions
% Yield in MeOH
(% Yield Neat)
Product
CHO
PEMB, AcOH
N
H
MeOH, 25 oC
72
(80)
Pr
0
(96)
Excellent for reductive aminations

Mild reducing agent for imines and oximes
Reaction with protic solvents is very slow
Soluble in aromatic hydrocarbons, alcohols and
92
(94)
Can be used solvent-free for reductive aminations

Chemically efficient: two-of-three hydrides are utilized
CHO
Pr2NH
CHO
C4H9
N
Pr
MeOH, 25 oC
PEMB
MeOH, 25 oC
PhNH2
H
N
C4H9
H
N
PEMB, AcOH
o
O
H3C
PhNH2
Ph
Ph
MeOH, 25 C
PhNH2
C3H7
PEMB, AcOH
MeOH, 50 oC
HN
H3C
Advantageous Properties of PEMB:
Ph
PhNH2
PEMB, AcOH
PEMB is a liquid Pyridine Borane Complex

useful for reductive amination chemistry.
Ph
C3H7
For more examples and experimental detail

Burkhardt, E. R.; Coleridge, B. M. Tetrahedron Lett. 2008, 49, 5152.
92
(93)
74
(94)
ether solvents
Add Aldrich to your research program.
Aldrich.com/pemb
Contact Aldrich Chemistry for
research quantities under 500 grams.
For quantities over 500 grams, contact BASF.
76684
ChiroSolv EnantioPrep Kits Deliver Pure

Enantiomers*
In 2007, Sigma-Aldrich began offering ChiroSolv Screening kits as useful
tools to identify the optimal chiral resolution conditions for racemates.
Very recently, Chirosolve, Inc. introduced ChiroSolv EnantioPrep Kits that
provide scalable, optimized chiral resolution methods and that deliver
pure enantiomers within a matter of days.
EnantioPrep is designed to obviate the obstacles analytical chemists face
during the elaborate process of diastereomeric crystallization. It offers
a well-established method to identify a comprehensive set of chiral
separation options, deliver pure enantiomers, and define a scalable chiral
separation. What sets EnantioPrep apart from other method development
tools is the inclusion of ChiroSolv Screening Kits that allow for 384 unique
reagent combinations to identify optimal separation conditions. It is an
extremely time and resource efficient approach to chiral resolution that
allows analytical chemists to skip over the hard part of finding an optimal
or scalable method to achieving an enantiopure product.
Key Features:
Four Screening Kits offer exhaustive screening to identify best

separation conditions
Purify Kits allow quick recovery of racemate
Self-contained design of the product allows streamlined and consistent
process for method development and to get pure enantiomer
Very little amount of racemate is needed (0.54 g)
Results within 2 weeks; up to 90% of theoretical enantiomer yield
One major advantage of diastereomeric crystallization is that the procedure scales up easily for manufacturing purposes. Today around 65% of
chiral products are made using this technique.
Examples:
Paroxetine is a selective serotonin reuptake inhibitor developed by
Novo Nordisks subsidiary, Ferrosan, and licensed to GlaxoSmithKline. It

is sold as the hydrochloride salt under the name Paxil for the treatment
of depression, anxiety, and obsessivecompulsive disorder. It is
prepared by resolution using ()-di-p-toluoyl-l-tartaric acid.
Setraline is an antidepressant that inhibits the uptake of serotonin in
the central nervous system and is sold by Pfizer under the name Zoloft.
Diastereomeric crystallization of the racemate by (R)-mandelic acid is
used in its preparation.
2-Amino-5-methoxytetralin is an intermediate in the synthesis of
N-0923 (Nagase & Co., Ltd., Japan), a potent dopamine D2 receptor
agonist, effective against Parkinsons disease (currently in clinical trial).
This intermediate is resolved by diastereomeric salt formation with
(S)-mandelic acid. The undesired isomer is then racemized and reused
in an iterative process.
In the synthesis of AG-7404 (Pfizer), a key intermediate was resolved
by ()-norephedrine. The final compound was obtained by the
combination of diastereomeric and enzymatic resolution.
How to Use ChiroSolv EnantioPrep Kits

Screen racemate against 384
separation conditions
Recover racemate using

recovery solution
Key Benefits:
Fast delivery of isolated enantiomer at a target purity and yield needing
Repeat until target

enantiomeric purity
is achieved
minimal amount of racemate
Cost-efficient method development through iterative crystallization

accelerates the lead optimization and preclinical studies

Consistent results provide solid basis for developing complete
separation strategy
Value-creating foundation builds differentiated patent estate
Works with any racemate (acid, base, alcohol, aldehyde, ketone, amino
acid, racemate with multiple chiral centers)
How do ChiroSolv Solutions Work?

ChiroSolv EnantioPrep Kits use the method of diastereomeric crystallization, a process that chemically separates enantiomers in a racemic
mixture by complexation with an enantiopure acid or base, resulting in
a mixture of diastereomeric salts. These salts have different chemical and
physical properties, which allow their separation. This well established
technology competes favorably with newer techniques such as asymmetric synthesis, biocatalysis, enzyme resolution, kinetic resolution, or chiral
chromatography.
Aldrich.com
Check purity
and yield
Extract purified
enantiomer ready
for testing
Purify racemate using the

best separation condition
Heat, Cool
The experiment involves Three phases of work:

1. Screening: Racemate is screened against 384 different combinations
of resolving agents and solvents. When the combination of
the racemate, resolving agent, and solvent is heated together,
diastereomeric salt of one enantiomer preferentially crystallizes out
after cooling. The best combination of the reagent and solvent that
offers the highest yield and enantiomeric enrichment for the target
enantiomer is chosen to do further enrichment.
2. Recovery: After collecting all the material used during the screening
process, which includes the racemate, resolving agents, and the
solvents, this phase will treat it with our recovery solution that will
separate out the racemate from the resolving agents in the form of two
Synthetic Reagents
liquid layers. Using separatory funnel, these layers will be separated and
the racemate (typically > 90%) will be recovered from the bottom layer
3. Purification: The goal of this phase is to identify how many
recrystallization steps are required to get the enantiomeric purity
needed. The end result should be a smaller quantity of enriched
enantiomer (maximum yield: about 35% of the total racemate given).
EnantioPrep allows scientists to:
Quickly screen a racemate against a comprehensive list of 384 resolving
agent/solvent combination to identify all possible resolution conditions
Recover the used racemate and proceed to purify it until target purity
is achieved
Define a step-by-step resolution method that can be scaled up to kilo

quantities
This purification solution can be used for racemic acids, bases, alcohols,
amino acids, aldehydes, and ketones.
EnantioPrep includes a set of four Acid or Base Series Screening Kits,
Recovery Solution for acid or base racemate that recovers up to 90%
racemate used during screening; and a self-contained Purification Package
that allows incremental purification of enantiomer through simple steps.
When the Recovery Solution is added to the diastereomeric salts of the

racemate and the resolving agents, it breaks the diastereomeric salt into
neutral racemate that goes in the organic layer; while the resolving agents
stay in the aqueous layer. Separating these two layers and removing the
residual solvents from the organic layer returns the original racemate.
The Purification Package includes a filter funnel with vacuum adapter,
enantiomer and filtrate collection bottles, spare filters, and pH paper.
After recovering the racemate from Screening Kits (using the Recovery
Solution), the resolving agent and solvent combination associated with
best separation condition is selected to get incrementally purified salt
of the target enantiomer until the required purity is achieved. Finally the
enantiomer is extracted from the diastereomeric salt. In our experience, if
you use 5 g of racemate during purification, depending on the number of
recrystallization steps needed, you can get up to 2 g of pure enantiomer.
The entire purification typically requires up to eight hours of hands-on
work giving results within one week.
Types of Kits
Acid
The acid screening kits include a distinct group of chirally pure acids and
is used to resolve racemic bases and amino acids (some pre-processing is
required for amino acids). Examples of resolving agents in the acid kits are:
()-Camphoric acid
(+)- and ()-Camphorsulphonic acid
(+)- and ()-Dibenzoyltartaric acid
()-Malic acid
(+)- and ()-Mandelic acid
(+)-Lactic acid
(+)- and ()-Tartaric acid
Example Kit.
Each individual screening kit is in a disposable, ready-to-use, 96-vial,

high-throughput format that allows the entire analysis to be performed
inside the kit without removing any vials. The kit is made of polypropylene
material that can withstand extreme temperatures (20 to 120 C),
allowing the entire kit to be placed in a hot-water or ice bath without
damage. The set of four screening kits offers unique 384 combinations of
resolving agent/solvent combinations, so that a full set of separation
conditions can be identified early on to help the rest of the research.
Resolving agents are chosen with manufacturing use in mind; they are
relatively inexpensive and recoverable in high yield after the resolution is
complete. The high-throughput format allows scientists to explore the
separation conditions in parallel and get results within 24 hours, which
may otherwise take over two months.
Base
The base screening kits include a distinct group of chirally pure bases or
amines, and is used to resolve racemic acids, alcohols, aldehydes, and
ketones (some pre-processing is required for the latter three). Examples of
resolving agents in the base kits are:
()-2-Aminobutanol
()-Brucine
()-Cinchonidine
(+)-Cinchonine
(+)-Dehydroabietylamine
(+)- and ()-Methylbenzylamine
(+)-Quinidine
()-Quinine
Ready to scale up? For competitive quotes on larger quantities or custom synthesis, contact your local Sigma-Aldrich office, or visit safcglobal.com.
Case Studies with ChiroSolv

EnantioPrep Solution
ChiroSolv EnantioPrep kits were used for
two sample racemates:
N-Benzyl-1-(4-methylphenyl)propane-2-amine (racemate had
70%S and 30% R isomer). Goal was to get over 90% purity for R isomer.
This racemate was resolved by di-tolyltartaric (+) acid in 100% IPA.
After two recrystallizations, we were able to obtain 30% S and 70% R.

Additional two recrystallizations yielded > 90% enrichment in R. The
yield was over 90% of theoretical value.
N-Benzyl-1-(4-benzylphenyl)propane-2-amine (racemate had
50%S and 50% R). Goal was to get over 90% purity of the R isomer. This
racemate was resolved by S-acetylmandelic acid (+) in 90% IPA. After
two recrystallizations, we were able to obtain 80% R and 20% S, with
yield over 80% of theoretical value.
Case Study Results

Racemate
Desired isomer purity
Starting material
Amount recovered
# of recrystallization
Amount of pure enantiomer
N-Benzyl-1-(4-methylphenyl)propane-2-amine
R isomer, >90% purity
1.046 g
0.996 g (95%)
280 mg
N-Benzyl-1-(4-benzylphenyl)propane-2-amine
R isomer, >90% purity
1.931 g
1.738 g (90%)
700 mg
Looking for a Safer

Fluorinating Reagent?
XtalFluor reagents are crystalline dialkylaminodifluorosulfinium
tetrafluoroborate salts. They are useful for the deoxofluorination
of hydroxyl and carbonyl moieties when used in conjunction with a
promoter.*
Enhanced thermal stability over
DAST and other structurally similar

deoxofluorination reagents
Broad substrate scope

Predictable and high
H3C
719439
products
OH
F F
H
F F
O
R
XtalFluor-M
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N=SF2 BF4
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Aldrich XtalFluor Reagents
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R
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Air-stable solids
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CH3
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* promoters: DBU, Et3N 3HF, or Et 3N 2HF
References: (1) Beaulieu, F. et al. Org. Lett. 2009, 11, 5050. (2) LHeureux, A. et al. J. Org. Chem.
2010, 75, 3401.
XtalFluor-E and XtalFluor-M are registered trademarks of OmegaChem Inc.
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sh4078
Synthetic Reagents
There are four Acid Series kits and four Base Series kits, available
individually, or as the complete acid or base set. Each individual kit is in
a ready-to-use, 96-vial, high-throughput format that allows the entire
analysis to be performed inside the kit without removing any vials.
The kit is made of polypropylene material that can withstand extreme
temperatures (20 to 120 C), allowing the entire kit to be placed in an
oven or ice bath without damage.
The kits can be supplied in two different formats, either as kits for solid
racemates or kits for liquid racemates. The kits for liquid racemates
provide calibrated quantities of a unique resolving agent and solvent
combination in each vial. The racemate can then simply be added to start
the screening process. The kits for solid racemates allow the researcher
to dissolve the racemate into a volatile solvent and then dispense the
resultant solution into each vial containing a resolving agent. The volatile
solvent is evaporated and the prepared screening solvents are then
dispensed from a separate plate into each vial.
Resolving agents are chosen with manufacturing use in mind; they
are relatively inexpensive and recoverable in high yield after the
resolution is complete. Using all four kits in an acid or base series, 384
resolving agentsolvent combinations can be explored for a single
racemate. The high-throughput format allows scientists to identify within
24 hours the optimum resolution process which might otherwise take
over two months.
ACID
BASE
12 so
lvent
s
Series 1
Series 1
8R
e
Ag solv
en ing
ts
Facile and Rapid Chiral Resolution with

ChiroSolv EnantioPrep Kits
96 vials
96 vials
Series 2
Series 2
96 vials
96 vials
Series 3
Series 3
96 vials
96 vials
Series 4
Series 4
96 vials
96 vials
384 combinations
Time Savings Using ChiroSolv Kits
No. of Days Required
25
20
15
10
5
0
16
32
48
96
144
192
240
288
336
384
No. of Resolving Agents

Manual Screening
Screening with ChiroSolv Kits
Synthetic Reagents
10
Recap: How to Use ChiroSolv Kits
Kits and vials have unique identification (barcode or alphanumeric) for
1. Choose the right kit type (Acid Series 1, 2, 3, 4 or Base Series 1, 2, 3, 4)

depending on the identity of the racemate.
2. If the racemate is an alcohol, amino acid, aldehyde or ketone, you may
need to pre-process the racemate.
3. Add 0.03 mmol of your racemate to each of the 96 vials. Depending on
the availability of the dispensing autostation and the racemate. type
(liquid or powder), you may need to remove the seal on the vials. Note
the seal is pierceable to accommodate direct injection of racemate by
liquid dispensers.
4. In an oven or water bath, heat the rack along with its vials to 80 C
(optimal temperature for most of these experiments) or until the
mixture becomes homogeneous.
5. Allow the kit to cool to ambient temperature. If required, further
cool it to 4 C or 0 C to observe crystallization. Vials with crystals are
considered positive results and should be examined further.
6. Often, more vials with positive results can be obtained using standard
crystal initiation techniques. Vials with no crystals even after this effort
are considered negative results.
7. Separate out the positive test results and note their alphanumeric
identification.
8. Liberate the enantiomers from their diastereomeric salts and analyze
by optical rotation. Typically, only one or two vials will show maximal
optical purity.
Long shelf life at room temperature (2 years).
Unknown Racemate
Heat mixture to 80100 C
Kits: A1, A2, A3, A4 or B1, B2, B3, B4
Select vials with crystals &

note their alphanumeric
identification
Cool mixture 4 C to 0 C
Analyze selected vials
with crystals for
specific rotation
Yes
Cool mixture to ambient temp.
resolving agentsolvent combinations.

Very little amount of racemate required (less than 3 mmol per kit).
Concentrations of the resolving agents are calibrated to give accurate
results and optimal crystallization.
Pierceable seal allows easy racemate dispensing; vials held together by
a plastic ring so that vials can be picked up and inspected together for
crystal formation.
Easy to follow, step-by-step instructions and results charts.
Conveniently designed for easy robotic manipulations.
Aldrich.com
Each vial contains a

unique combination of
resolving agent/solvent
8 types of kits give 768 such
combinations.
Pierceable septa or foil

seal for easy
robotic manipulation.
Plastic sleeve holds

the vials together even
when they are out of
the rack.
Each rack has a

unique barcode.
Extra septum mat
provided in kits for
solid racemates.
Each vial has a unique

alphanumeric identification.
Rack, vials, and septa

are chemically inert
and can withstand
20 C to 120 C.
Product Information for Liquid Racemates

Product No.
681431
681423
681415
699217
700363
681407
681393
681377
699241
700371
Product Name/Description
ChiroSolv Resolving Kit, Acid Series 1
ChiroSolv Resolving Kit, Complete Acid Series
ChiroSolv Resolving Kit, Base Series 1
ChiroSolv Resolving Kit, Complete Base Series
Product Information for Solid Racemates
Eight types of ready-to-use disposable kits providing a total of 768
Ready to Use Disposable Kit
No
Features
cross-referencing.
Product No.
698881
699527
698873
699225
700398
699233
698938
698946
698954
700401
Product Name/Description
ChiroSolv Resolving Kit, Complete Acid Series
ChiroSolv Resolving Kit, Complete Base Series
For more information, please visit Aldrich.com/chirosolv
Need a MolarMatic
Measuring Cylinders
for your Acid solutions?
Aldrich MolarMatic Measuring Cylinder

Our MolarMatic graduated measuring cylinder allows you to
add concentrated acid to the desired molarity line. Simply pour
the measured acid into one liter of water, and your 1 M, 2 M, or
3 M solution is prepared.
No calculations
No struggling for the correct cylinder
Convenient Dual-Scale Graduated Cylinder
Class A, 350-mL cylinders

Graduated in 5.0-mL increments; calibrated "to deliver"
1 to 3 Molar scale on opposite side
Eliminates repetitive molar calculations and potential errors
Set contains one of each cylinder in plastic storage case
Acid Type
Cat. No.
Acetic acid
Z683728
Hydrochloric acid
Z683736
Nitric acid
Z683744
Sulfuric acid
Z683752
Set of four
Z683760
Save time. Add Aldrich.
Aldrich.com/molarmatic
75634
12
Catalysis
Ronaldo Mariz, Ph.D.
Product Manager
ronaldo.mariz@sial.com
Zaca Catalyst: Enabling Flexible Asymmetric

Synthesis Through Carboalumination of
Terminal Alkenes
Since the seminal work of Nobel laureate Ei-ichi Negishi using ZACA
catalyst (719072),1 the zirconium catalyzed asymmetric carboalumination
reaction (ZACA reaction) of terminal alkenes has allowed highly flexible design for the syntheses of chiral organic compounds. For instance,
proper treatment of the carboaluminated intermediate from inexpensive
allyl alcohol gives rise to versatile building blocks through a one-pot
procedure which can undergo further Pd-catalyzed functionalization
(Scheme 1).2
HO
1) Me3Al (2.5 eq)

2) 719072 (5 mol%)
MAO (1 eq)
I2
(2.5 eq)
Me
AlMe2
Me2AlO
CH2
l, DM
TBSC
(-)-ZACA catalyst - (R)-product
(+)-ZACA catalyst - (S)-product
TBSO
82%
[Pd]
[Pd]
Me
TBSO
HO
[Pd]
[Pd]
Me
CH2
TBSO
*
80%
Me
TBSO
Me
TBSO
Me
TBSO
CH2
52%
TBSO
I
HO
1) (i) (+)-ZACA;
(ii) Pd-cat.vinylation
2) (i) (+)-ZACA; (ii) O2
Me
Me
Me
OH
O
O
H
MeN
N
H
O
1) NaH, BnBr
2) TBAF
3) Dess-Martin oxid.
4) EtO2CCH=PPh3
OH
77% (4 steps)
Me
(R)
Me
(S)
(S)
Me
steps
Me
EtO2C
Me
Me
OBn
(R)
(S)
(S)
Scheme 2: Sequential ZACA reaction to construct multiple stereogenic centers.
Me
CO2Me
Me
I
H3O+
Me
Me
doliculide
Me
Me
Me2AlO
Probing its flexibility, Negishis group has demonstrated that when

followed by vinylation the ZACA reaction can be sequentially used to
construct multiple stereogenic centers. This methodology furnishes an
elegant entry to deoxypolypropionate, residues present in many natural
products with interesting medicinal properties and biological activity
such as doliculide (Scheme 2).2,3
References: (1) (a) Kondakov, D. Y.; Negishi, E. J. Am. Chem. Soc. 1995, 117, 10771. (b)
Kondakov, D. Y.; Negishi, E. J. Am. Chem. Soc. 1996, 118, 1577. (2) Liang, B.; Novak, T.; Tan, Z.;
Negishi, E. J. Am. Chem. Soc. 2006, 128, 2770. (3) Negishi, E. ARKIVOC 2011, viii, 34.
O
H3C
Me
CH3
H3C
TMS
*
Cl Zr Cl
Scheme 1: One-pot procedure for the synthesis of versatile protected and

unprotected 3-iodo-2-methyl-1-propanol via ZACA reaction.
H3C
(-)-ZACA catalyst
719072
CH3
CH3
For a list of zirconium catalysts available from Aldrich Chemistry,

visit Aldrich.com/zirconium
Aldrich.com
Catalysis
p-Tol-BINASO: A Highly Active and Selective

Ligand for Rhodium-Catalyzed Asymmetric
Conjugated Addition
Aldrich Chemistry is pleased to offer researchers this promising chiral

sulfoxide ligand.
CH3
The rhodium-catalyzed asymmetric 1,4-addition reaction has emerged

as a powerful tool for the formation of C-C bonds over the last decade.1
Recent reports by the group of Prof. Dorta at the University of Zrich
showed excellent results by using a C2-symmetric bis-sulfoxide ligand
based on the binaphthyl moiety. High activity and selectivities were encountered in the addition of boronic acids to ,-unsaturated cyclic esters
and ketones under mild conditions when applying rhodium p-Tol-BINASO
complex (Scheme 1).2
O
+
[(p-Tol-BINASO)]RhCl]2
(1.5 mol% Rh)
1.1 eq. ArB(OH)2
Ar =
CF3
2.0 h
1.0 h
1.5 h
1.0 h
98% yield, 90% ee 60% yield, 99% ee 93% yield, 99% ee 94% yield, 97% ee
Cl
OMe
CH3
1.5 h
93% yield, 99% ee
726443
726435
(P,S,S)-p-Tol-BINASO
726443
726443
CH3
CH3
For a list of chiral catalysts and ligands available from Aldrich

Chemistry, visit Aldrich.com/asymmetriccatalysis
Takasago Ligands and Complexes: Excellence in

Catalysis Technology Now at Reduced Prices
Ar
F
CH3
1.0 h
99% yield, 98% ee
S
O
O
S
(M,S,S)-p-Tol-BINASO
O
X
KOH (50 mol%)

toluene/H2O (10/1)
40 C
CH3
Ar =
S
O
O
S
CH3
The research team at Takasago International Corporation has developed

excellence in catalysis through continuous improvements for over a
quarter century. This work has translated into cutting edge catalysis
technology for many chemical transformations with special emphasis on
asymmetric synthesis (Scheme 1).
Reduction of ketones to
alcohols or amines
Cl
1.0 h
1.5 h
1.0 h
1.0 h
OH
R2
R1
R2
R1
or
Arylation and vinylation

of ketones
O
NH2
OH
R2
R1
R2
R1
R1
Ar =
R3
R2
R3 = vinyl, aryl
OMe
F
1.5 h
90% yield, 98% ee
Fluorination
1.0 h
1.0 h
1.0 h
1.0 h
O
CO2t-Bu
O
H3C
O
Ph
Ph
Ph
H3C
2-naphthyl
Conversion of allylamine to aldehydes

R2
CO2t-Bu
R2
R1
N
R3
R3
R1
O
H
X = O, NH, NR
Buchwald-Hartwig Amination and Suzuki cross-coupling
2-naphthyl
0.5 h
1.0 h
3.0 h
99% yield, 96% ee 98% yield, 66% ee 98% yield, 91% ee 1.0 h, 98% yield, 94% ee (1:1 cis:trans)
R1
or
Scheme 1: Rhodium-catalyzed 1,4-addition of boronic acids to ,-unsaturated

esters and ketones using p-Tol-BINASO.
While an excess of boronic acid was required for most systems used for
this transformation, the ligand enabled coupling of ortho, meta, and para
substituted aryl boronic acids using only 1.1 equivalents of the nucleophile. In addition, only 1.5 mol% of rhodium is needed instead of the
3mol% normally required to preform the reaction in short time at a mild
40 C, which is in contrast to the higher temperatures frequently applied.
H
N
R3
+
R3
R1
N
R2
R2
or
R3
Ar
Ar B(OH)2
Reduction of Alkenes
R2
R1
Cyanomethylation
R2
R3
R1
O
R3
R1
OH
H
R1
CN
Scheme 1: Examples of reactions performed by Takasago ligands and complexes.
References: (1) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829. (2) (a) Mariz, R.; Luan,
X.; Gatti, M.; Linden, A.; Dorta, R. J. Am. Chem. Soc. 2008, 130, 2172. (b) Burgi, J.; Mariz R.;
Gatti, M.; Drinkel, M.; Luan, X.; Blumentritt, S.; Linden, A.; Dorta, R. Angew. Chem. Int. Ed.
2009, 48, 2768. (c) Mariz, R.; Brgi, J.; Gatti, M.; Drinkel, E.; Luan, X.; Dorta, R. Chimia 2009,
63, 508. (d) Mariz, R.; Poater, A.; Gatti, M.; Drinkel, E.; Burgi, J.; Luan, X.; Blumentritt, S.; Linden,
A.; Cavallo L.; Dorta, R. Chem. Eur. J. 2010, 16, 14335.
13
14
Aldrich Chemistry is pleased to offer the over 70 Takasago ligands and

complexes at reduced prices.
New Palladium Catalysts and Precursors for

Cross-coupling Reactions
O
O
PPh2
PPh2
CH3
PPh2
PPh2
P(t-Bu)2
693065
692395
PPh2
PPh2
CH3
P(t-Bu)2
PCy2
O
O
O
R R
P Cl
Ru
P Cl
R
R
H2
N
Ph
N
H2
Ph
Cl
H3CO
t-Bu OCH3
OCH3
732117
704946
PCy2
Ph
Pd
i-Pr
Ph Ph
Ph
P
O
NH2
Pd
Cl
i-Pr
i-Pr
702951
O
CH3
NH2
Pd Cl
CH3
H3C
702943
CH3
H3C
Cl Pd Cl
CH3
693537
693383
CH3
H3C
711179
OMe
PPh2
692387
CH3
H3C
i-Pr
i-Pr
692344
708739
NH2
Pd Cl
R=
CH3
i-Pr O
693200
t-Bu
t-Bu
i-Pr
704954
CH3
NH2
Cl
Pd
NH2
Cl
P
t-Bu OCH3
H3CO
i-Pr
i-Pr
For a complete list of Takasago ligands and complexes,

visit Aldrich.com/takasagocatalysts
O i-Pr
707589
OCH3 i-Pr
718750
A comprehensive list of palladium catalysts and precursors for crosscoupling reactions is available from Aldrich Chemistry in a useful
application guide format, Aldrich.com/pdapplicationguide
Need Chemical Compounds

for Your Research?
Let us supply the chemicals so you can concentrate
on the science!
Aldrich Custom Packaged Reagents
Aldrich.com/CPR
AldrichCPR@sial.com
AldrichCPR provides pre-weighed, application ready building blocks

and screening compounds, allowing you to focus on discovery rather
than the tedious process of sourcing, procurement, and preparation.
Provide your list of MFCD numbers, CAS numbers, CNC IDs, structures,
and/or vendor and product numbers, and Aldrich Chemistry will source,
package, and send your chemicals to you.
76758
Aldrich.com
Br
BF3K
BF3K
681342
662984
BF3K
N
H
Br
BF3K
711144
729299
BF3K
BF3K
CI
723797
KF3B
728837
N
N
When you need a

Trifluoroborate for
your cross-coupling.
NH
F
B F
F
OCH3
S
710075
728810
Air and moisture stability

Less prone to protodeboronation
Stability to common and harsh reagents, and
CH3
N
NH
Continually introducing new and innovative Boronic

Acid Surrogates to meet your research needs, our
vast line of organotrifluoroborates feature:
BF3K
H2C
CH3
BF3
723916
710083
reaction conditions
From the latest product innovations to the widest

selection of solvents on the market, your research
will move forward faster when you add trustworthy
products, services, and information from
Aldrich Chemistry.
Add Aldrich to your research program.
BF3K
CH3
CH3
720747
H3C
BF3K
CH3
Aldrich.com/tfb
720682
76253
16
Organometallics
Aaron Thornton, Ph.D.
Product Manager
aaron.thornton@sial.com
EZ-CrotylMix: A Comprehensive Solution to the

Enantioselective Crotylation of Aldehydes
Enantioselective crotylation reactions have been the focus of an
enormous amount of effort within the field of organic synthesis. This
reactions ability to form C-C bonds, as well as set adjacent stereocenters,
has been critical to the construction of numerous complex molecules.
The first general approach to this transformation was disclosed by
Professor H.C. Brown and co-workers in 1986, in the form of their chiral
crotylborane methodology (Scheme 1).
While these reagents have made significant strides in addressing many

of the previously mentioned shortcomings of the Brown method, still an
overall lack of substrates that undergo productive reaction with these
reagents significantly limits their application (Scheme 3).
BnO
OH
CH3
B
CH3
CH3
B
CH3
CH3
Despite the fact that Browns methodology has been the method of
choice for the past 20 years, significant shortcomings remain. Of particular
importance is the inherent diastereofacial bias of certain chiral aldehydes
that is often difficult, or even impossible, to overcome. Also, the Brown
method is hampered by the use of somewhat impractical synthetic
techniques, including the use of harshly basic organometallic species,
air and moisture sensitive Lewis acids, and the need for low temperature
manipulations.
The group of Professor James Leighton previously developed reagents for
the enantioselective crotylation of aldehydes based on the use of their
chiral crotylsilanes (Scheme 2).1
N
N
Br
H
Si
CH3
Cl
Si
Cl
Br
733180
N
N
CH3
Si
CH3
733199
H
or
733180
Ph
OH
733083
CH3 CH3
5 mol% Sc(OTf)3
CH2Cl2, 0 oC
Cl
CH3
Cl
Br
733199
Br
733075
Scheme 2: Leightons crotylsilane reagents.
Aldrich.com
OH
CH3
No Reaction
733199
or
733180
Ph
CH3
O
Ph
CH3
OH
733075
H
5 mol% Sc(OTf)3
CH2Cl2, 0 oC
Ph
Scheme 4: Sc(OTf )3 catalyzed enantioselective aldehyde crotylation.
CH3
Si
CH2Cl2, 0 C
BnO
87% yield
91% ee
Br
Based on the knowledge that Lewis acids may be used to catalyze the
reaction of similar allylboranes with aldehydes by binding to one of the
boronate oxygen atoms, the Leighton group hypothesized that a similar
strategy may be useful for activating their crotylsilane reagents. Now, with
the addition of just 5 mol% Sc(OTf )3, the enantioselective crotylation of
previously unreactive aldehydes may now be performed with excellent
yield and enantioselectivity (Scheme 4). Importantly, this new method
utilizes air-stable crystalline solids that can easily be weighed out and
manipulated at room temperature.2
Br
733180
Scheme 3: Representative examples of successful and unreactive substrates.
733083
Br
CH3
Scheme 1: Browns chiral crotylboranes.
Br
BnO
83 % yield
99 % ee
Ph
Ph
O Si
O
H3C
CH2Cl2, 0 C
CH3
CH3
B
82 % yield
96 % ee
H3C
CH3
733199
CH3 CH3
87% yield
94% ee
Organometallics
To further increase the utility of this method, the Leighton group has
shown that simply premixing the chiral crotylsilane reagent and Sc(OTf )3
leads to a versatile reagent that simplifies reaction set-up even further.
This bench-stable reagent, termed EZ-CrotylMix, can now be used for
the enantioselective crotylation of previously unreactive substrates, with
the crotylation of -methylcinnamaldehyde yielding the desired product
in 89 % yield with 92 % ee (Scheme 5).
H 3C
H3C
Ph
Ph
O Si
O
CH3
(R,R)-trans EZ-CrotylMix
(737674)
CH2Cl2, r.t.
H3C
H3C
Chiral Crotylsilanes and EZ-CrotylMixes from Aldrich

Br
H
Ph
CH3
(S,S)-cis EZ-CrotylMix
(737666)
CH2Cl2, r.t.
H
Si
N
N
CH3
Cl
Br
733083
Br
H
CH3
Si
Cl
N
N
CH3
Si
Cl
Br
Br
733199
Br
Scheme 5: EZ-CrotylMix for the enantioselective crotylation of aldehydes.

H
N
N
733075
Sc(OTf)3
Br
H
Si
Cl
CH3
H
Br
Crystalline solids that can be weighed in air on the benchtop

Provide excellent reactivity and selectivity
Have a truly broad substrate scope
N
N
Si
Br
Br
Sc(OTf)3
H
Cl
25
737666
Sc(OTf)3
Br
CH3
N
Si
Br
25
737682
CH3
Si
Sc(OTf)3
CH3
Cl
25
737674
References: (1) Hackman, B. M.; Lombardi, P. J.; Leighton, J. L. Org. Lett. 2004, 23, 4375. (2)
Kim, H.; Ho, S.; Leighton, J. L. J. Am. Chem. Soc. 2011, 133, 6517.
Si
Br
CH3 CH3
To learn more about Leightons EZ-CrotylMix reagents available

from Aldrich Chemistry, visit Aldrich.com/ezcrotylmix
733180
89% yield
92% ee
Cl
CH3 CH3
Aldrich Chemistry has now teamed with Prof. Leighton to make these
powerful reagents commercially available. These reagents show a number
of advantages over previously developed crotylation products, including:
CH3
Br
Ph
Ph
O Si
OH
OH
Ph
85% yield
97% ee
O
Br
Cl
Br
25
737658
17
18
Building Blocks
Mark Redlich
Product Manager
mark.redlich@sial.com
Halogenated Pyridines
New Halogenated Pyridines continued
Pyridines continue to be extremely popular building blocks for synthetic

chemists across a number of disciplines. The pyridine moiety is found in a
wide range of synthetic targets with applications in catalysis, drug design,
molecular recognition, and natural product synthesis. Halogenated
pyridines in particular are attractive building blocks for various cross-coupling methodologies. Aldrich Chemistry offers these useful halogenated
pyridines for your research.
Br
724793
730181
Br
725188
Cl
O
F3C
Br
OH
Br
722448
NH2
Br
728675
723339
F
NH2
Br
Br
733997
N
H
Br
Br
Br
NO2
714585
Cl
729450
H
H3CO
715778
728985
714526
OH
NH2
O
H
725064
Cl
NH2
NH2
725021
H
OCH3
Cl
CH
724300
O
I
Cl
S
O
716553
725196
Cl
Br
725072
720232
Br
731072
New Aldehydes
HO
CH3
For a complete list of available halogenated pyridines available from

Aldrich Chemistry, visit Aldrich.com/hal-pyr
Cl
CF3
728748
733237
Br
NO2
SH
F3C
722391
New Halogenated Pyridines
NH2
H3C
Br
NH2
H
N
725056
714658
732176
Cl
OCH3
Cl
715786
725722
732508
O
O2N
Cl
N
724297
Cl
O2N
Br
N
730157
Cl
Cl
F
N
NH2
H
H3C
714631
Br
732494
For a complete list of available aldehydes available from Aldrich

Chemistry, visit Aldrich.com/aldehyde
Aldrich.com
Building Blocks
Other New Building Blocks
Cl
Cl
O
O
H3C
Br
CN
CH3
714984
734454
731315
OCH3
CH3
715344
N
N
730203
NH2
707120
O
I
N
H
N
H
731935
HN
CH3
OCH3
HN
N
732125
Br
N
Cl
728772
Cl
O
Cl
Br
732842
Cl
I
O
732869
O
Cl
Br
732095
732877
CF3
Cl
Cl
H2N
N
NH2
709131
N
N
732281
H2N
732133
For a comprehensive list of building blocks available from Aldrich

Chemistry, visit Aldrich.com/bb
To discover Microreactor
Technology & Flow Chemistry
Microreactor Explorer Kit
Our all-in-one solution allows you to explore innovative new
technologies right away at a highly attractive price:
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Microreactor Explorer Kit
Product No.
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19
20
Specialty Synthesis
Pietro Butti, Ph.D.
Product Manager
pietro.butti@sial.com
Ionic Liquids: A Smart Alternative

Environmentally low-impact alternatives, sustainable processes, industrial
ecology, and efficiency are some of the topical words which are directing
the development of the new generation of technologies and products.1
Therefore, the importance of compounds coming from renewable feedstock or enabling high levels of recycling is growing exponentially. These
compounds are seen as promising materials able to replace compounds
produced with fossil fuel sources, hence reducing our global dependence
upon them.2
R
N
R'
N
R
R''
R'''
R
R''
R'
R'''
BF4
PF6
OTf
CH3COO
R2PCl
MesN
Cl
Ionic liquids have been recognized and developed by scientists from

academia and the chemical industry as new green(er) chemicals.3 Even if
they are not always the greenest choice, 4 ionic liquids, a group of salts
that exist as liquids at relatively low temperatures (<373 K) (Figures
1 and 2), have gained overwhelming interest over the past decades
(Chart1). They offer unique sets of properties, often difficult to achieve
with any other compounds. Some of these properties are chemical and
thermal stability, non-flammability, and low vapor pressures.5
Publications per Years
5000
4500
Number of Pubications
4000
3500
3000
2500
2000
Ts
N
H2C
Ionic liquids are also used in polymer and biopolymer processing as

enabling technology to utilize cellulose.1,8 In electrochemical applications
and in metal processing9 they offer unprecedented prospects for metal
deposition. Furthermore, they can be used in nuclear fuel processing.10
They lead to new opportunities in separation processes, or their tuneable properties can be exploited to prepare engineering fluids or other
high-performance materials. Ionic liquids are also used in analytical
chemistry11 (Supelcos GC capillary column SLB-IL series) and biomedical
applications.12 These examples highlight just a few of the large number of
potential applications in which this class of extraordinary compounds can
be used.
10
09
20
20
08
07
20
20
05
06
20
04
20
20
03
02
20
20
01
00
20
20
99
98
19
19
97
96
19
19
95
94
19
19
93
92
19
19
Ts
N
Scheme 2: Recyclable catalytic system for a model metathesis reaction.7
0
90
5 mol%,
BMIM PF6 (70956)

CH3
CH3 CH2 Tol, 3h, 25C
Up to >98% Conversion
5 Cycles
500
91
CH3
1000
19
PF6
Cl
1500
19
NMes
Ru
Cl
H3C
Figure 2: Commonly used ionic liquids aprotic anions.
Year
Chart 1: Number of SciFinder hits containing the words Ionic Liquids from 1990 to
2010. Red total number of publications, Gray filtered through patent applications.
Aldrich.com
N ClH
Another example is the olefin metathesis, published by Grela and

co-workers in 2007 (Scheme 2).7
Water Miscibility
Publications per Years
R2POEt +
Recycle
CF3COO
NO3 Br
N
+
EtOH
Scheme 1: Preparation of alkoxyphenylphosphines (R2POEt) with the BASIL process.6
R''
R'
Figure 1: Commonly used ionic liquids aprotic cations.

NTf2
This class of compounds opens up a variety of opportunities in many different applications. For example, chemical processing and fine chemicals
synthesis such as the BASIL process (Scheme 1).6
Specialty Synthesis
References: (1) Pinkert, A.; Marsh, K. N.; Pang, S.; Staiger, M. P. Chem. Rev. 2009, 109,
67126728. (2) Xie, H.; King, A.; Kilpelainen, I.; Granstrom, M.; Argyropoulos, D. S. Biomacromolecules, 2007, 8, 3740. (3) Keskin, S.; Kayrak-Talay, D.; Akman, U.; Hortacsu, O. J. of
Supercritical Fluids, 2007, 43, 150180. (4) Jessop, P. G. Green Chem., 2011, article in press
DOI: 10.1039/C0GC00797H (5) Zhu, S.; Wu, Y.; Chen, Q.; Yu, Z.; Wang, C.; Jin, S.; Ding, Y.; Wu,
G. Green Chem., 2006, 8, 325. (6) Maase, M. Multiphase Homogeneous Catalysis, 2005, 2,
560566. (7) Rix, D.; Cajo, F.; Laurent, I.; Gulajski, L.; Grela, K.; Mauduit, M. Chem. Commun.,
2007, 37713773. (8) Maase, M.; Massonne, K.; Uerdingen, E.; Vagt, U.; ChemFiles, 2006,
6(9), 3 (9) Abbott, A. P.; Frisch, G.; Hartley, J.; Ryder, K. S. Green Chem., 2011, 13, 471481. (10)
Nash, K. L; Lumetta, G. J. Advanced Separation Techniques for Nuclear Fuel Reprocessing and
Radioactive Waste Treatment. 2011, 1. (11) Soukup-Hein, R. J.; Warnke, M. M.; Armstrong, D.
W. Annual Rev. Anal. Chem., 2009, 2, 145168. (12) Elliott, G. D.; Kemp, R.; MacFarlane, D. R.;
Plechkova, N. V.; Rogers, R. D.; Seddon, K. R. Ionic Liquids: From Knowledge to Application.
2009, 6, 95105.
CH3
N+
N
CH3
H3C
CH3
H3C
713198
Br
N+
H3C
CH3
713171
H3C
O
O
F3C S N S CF3
O
CH3 O
H3C
713155
N+
CH3
H3C
H3C
H3C
PF6
PF6
CH3
713090
N+
N
CH3
I
CH3
713031
H3C
N+
CH3
N
O
O
CH3
H3C N
NH2
H3C N
OH
728527
CH3
CH3
I
H3C
O
O
F3C S N S CF3
CH3 O
O
N+
CH3
N
O
O
CH3
NH2
CH3
H3C N
727903
H3C
HO
726257
O
O S
O
CF3
CH3 O S O
N
N
O S O
CH
3
CH3
CF3
O
727679
CH3
N+
N
N+
CF3
O S O
N
O S O
CH3
CF3
727954
CH3
I
CH3
CH3
N
CH3 CH3
727989
713074
713066
CH3
N
727687
CH3
BF4
O
O
F3C S N S CF3
O
O
727695
727911
713015
713082
N+
CH3
CH3
N+
PF6
CH3
N
713023
CH3
H2C
H3C N
727709
H3C
N+
CH3
N+
CH3
727725
N
C
N
C
N
727717
713120
CH3
BF4
N+
N
713104
H2C
713163
713139
O
O S CF3
O
CH3
H3C N
CH3
713112
H3C N
N+
H2C
BF4
N+
CH3
H3C N
N+
N+
BF4
N+
713007
CH3
H3C N
PF6
O
O
CH3 F3C S N S CF3
O
O
CH3
H3C N+
CH3
711705
For a complete list of ionic liquids, available from Aldrich Chemistry,

visit Aldrich.com
N+
O
O
F3C S N S CF3
O
O
21
CH3
713058
CF3
O S O
N
O S O
CF3
22
Stable Isotopes
Leslie Patterson, Ph.D.
Product Manager
leslie.patterson@sial.com
Aldrich NMR Solvents

Challenge Us And See Why Our Quality is
Unsurpassed!
High quality NMR solvents are essential for satisfying the most rigorous
demands of NMR-based research and analyses. At Aldrich, we are passionate about providing this high level of quality to our customers and
work continuously to meet these requirements. We offer the widest
range of NMR solvents with the highest isotopic enrichment available
along with excellent chemical purity. We consistently review and improve our methods for solvent purification and for the reduction of water
content in our already high quality NMR solvents. All of our NMR solvents
undergo thorough quality control testing during the manufacturing and
packaging processes to verify the product quality is preserved.
Aldrich Chemistry also offers unparalleled convenience and service. Our

award-winning website allows for quick product searching, easy ordering,
and a wealth of valuable tools and information to aid your research efforts.
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Try our NMR Solvents today to see their high quality for yourself.
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Use and Handling of NMR Solvents

Most deuterated NMR solvents readily absorb moisture. To minimize the chance of
water contamination, use carefully dried NMR tubes and handle NMR solvents in a
dry atmosphere.
How to Obtain a Nearly Moisture-free Surface
1. Dry glassware at ~150 C for 24 hours and cool under an inert atmosphere.
2. Rinse the NMR tube with the deuterated solvent prior to preparing the sample.
This allows for a complete exchange of protons from any residual moisture on
the glass surface.
3. For less demanding applications, a nitrogen blanket over the sample preparation setup may be adequate.
How to Avoid Sources of Impurities and Chemical Residues
1. Use clean, dry glassware and PTFE accessories.
2. Use a vortex mixer instead of shaking the tube contents. The latter action can
introduce contaminants from the NMR tube cap.
How to Remove Solvent Residue

1. Protonated solvent residue can be removed by co-evaporation.
2. Use a small quantity of the desired deuterated solvent, a brief high vacuum
drying (510 min), and then prepare the NMR sample.
3. Solvents such as chloroform-d, benzene-d6, and toluene-d8, also remove
residual water azeotropically.
How to Avoid TMS Evaporation
1. Extended storage of TMS-containing solvents can lead to some loss of TMS.
Storing these solvents in Sure/Seal bottles virtually eliminates such a loss.*
2. Purchase TMS-containing solvents in single-use ampules.
*
T o dispense the product from Sure/Seal bottle or septum vials, use standard
syringe needle techniques. For details and recommended procedures, please
refer to Aldrich Technical Bulletin AL-134 or visit our Web site at Aldrich.com.
3. Residual chemical vapor from equipment can be a source of impurities;

residual acetone in pipette bulbs is a common example.
Aldrich.com
Stable Isotopes
Specialty NMR Solvents
Anhydrous NMR Solvents
Aldrich Chemistry offers a wide range of high purity deuterated solvents

for the NMR community. In addition, we also offer various specialty
solvents for more demanding applications. Whether you need the highest enriched deuterium oxide available, or solvents with a reduced HOD
peak, we have what you need.
When water content is of paramount concern, try our anhydrous

solvents that contain reduced levels of water.
Acetonitrile-d3, 99.8 atom % D, Anhydrous (water < 10 ppm)
569550-10X1ML
ampule
10 x 1 mL
Benzene-d6, 99.6 atom % D, Anhydrous (water < 10 ppm)
570680-50G
glass bottle
50 g
Special HOH Solvents

When customers requested NMR solvents with a suppressed HOD peak
we listened, and developed NMR solvents called Special HOH. These
solvents have an HOD peak which is less than 1% of the HOH peak, to
minimize potential exchange with an analyte. Special HOH solvents also
meet our standard water specification for NMR solvents.
H-NMR Spectrum of DMSO-d6 Special HOH
Acetonitrile-d3, 99.8 atom % D, "Special HOH"

699543-10G
glass bottle
699543-25G
glass bottle
699543-50G
glass bottle
Dimethyl sulfoxide-d6, 99.9 atom % D, Anhydrous (water < 50 ppm)

570672-50G
glass bottle
50 g
569585-5X1ML
ampule
5 x 1 mL
569585-10X1ML
ampule
10 x 1 mL
Methanol-d4, 99.8 atom % D, Anhydrous (water < 50 ppm)
570729-50G
glass bottle
50 g
569534-5X1ML
ampule
5 x 1 mL
569534-10X1ML
ampule
10 x 1 mL
10 g
25 g
50 g
Dimethyl sulfoxide-d6, 99.9 atom % D, "Special HOH"

612324-25G
glass bottle
612324-50G
glass bottle
612324-100G
glass bottle
716731-10x0.75ML
ampule
716731-10ML
serum vial
716731-50ML
serum vial
Chloroform-d, 99.8 atom % D, Anhydrous (water < 10 ppm)

570699-50G
glass bottle
50 g
25 g
50 g
100 g
10 x 0.75 mL
10 mL
50 mL
Toluene-d8, 99.6 atom % D, Anhydrous (water < 10 ppm)

570710-50G
glass bottle
Extra Enriched D2O

With an enrichment of 99.994 atom % D, this is the highest enriched
deuterium oxide available.
Deuterium oxide, Extra, 99.994 atom % D
613398-10G
serum bottle
613398-50G
serum bottle
HOH
DMSO-d6
residual peak
For additional information visit Aldrich.com/nmr

or contact:
HOD
3.3
ppm
11.5
11.0
10.5
10.0
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
ppm
5.0
2.5
ppm
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
2.4
0.5
0.0
0.5
50 g
Stable Isotope Technical Service

Phone:
(937) 859-1808

(800) 448-9760 (US and Canada)
Fax:
(937) 859-4878
E-mail: isosales@sial.com
Data acquired on a Varian 400 MHz instrument.
10 g
50 g
23
Stockroom Reagents
24
Stockroom Reagents
Todd Halkoski
Market Segment Manager, Solvents and Reagents
todd.halkoski@sial.com
Sigma-Aldrich is a Leading Global Supplier and

Manufacturer of High Quality, Stockroom and
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We specialize in providing the most comprehensive product range
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Pressure Conversion Tab: Use the built-in Pressure Conversion Calculator
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Temperature Conversion Tab: Quickly calculate temperature conversions
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Printable: Need a hard copy to take with you? Simply right-click and
select 'print'.
Aldrich.com/nomograph
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Need a Molarity
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76070
26
Labware Notes
Paula Freemantle
Product Manager
labware@sial.com
Aldrich Rotary Evaporator Replacement

Glassware
Cross-referenced with Buchi part numbers

Plastic-coated and uncoated versions
Jointed flasks compatible with most evaporators
This heavy-duty glassware is designed to fit Buchi rotary evaporators

and is cross-referenced with Buchi part numbers to aid in selection. The
condensers and flasks are available in non-coated glass for maximum
resistance to solvents and heat, and with poly coating for extra protection
from breakage. The jointed flasks and splash-guard adapters will fit most
brands of rotary evaporators. Note that 35/20 and 35/25 spherical joint
components are interchangeable.
Premium quality glassware, widest range, low cost
Condenser Assemblies and Components

Drying Flasks with Indents
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Large Evaporator Flasks
Receiving Flasks Adapters
Receiving Flasks
Splash Guard Adapters
Vapor Duct Tubes
To see the complete range of products or to place orders,
visit Aldrich.com/evapglass
Z682055
Z515515
Z682713
Z682829
Z549193
Z682187
Z682918
Z682411
Aldrich.com
Labware Notes
Aldrich Rotary Evaporator Adapter Set

This versatile adapter connects jars and bottles to the vapor tube of a rotary
evaporator. Precision machined from durable, chemically inert glass-filled
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Attach the other end of the adapter to the vapor tube via standard taper
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top cap with PTFE liners, and a 200 mL borosilicate glass jar.
Julabo Economy Series

Refrigerated/Heating
Circulators
Compact design
Temp. range -20 to 100 C
0.35 bar pump pressure
15 L/min pump flow
Cooling capacity 120 W, at 0 C
200 W, at 20 C
Heater capacity 2 kw
Bath opening W L D

15 cm 16 cm 13 cm
Overall W L H
20 cm 36 cm 56 cm
Volume 4.5 L
Z557285-1EA
Z653209-1EA
Z723169-1EA
Z723177-1EA
115 VAC
230 VAC
24/40 joint
29/32 joint
News and Innovation

Aldrich FKM sleeve stopper septa
Sealability Factor
These new septa are made from fluoroelastomer FKM which is highly
resistant to a broad range of solvents. An elastomer study done at
Sigma-Aldrich compared the solvent compatibility (resistance) of FKM
and EPDM rubber (Figure 1). A Sealability Factor was determined
for each elastomer. The lower the number the more compatible the
rubber is with a solvent.
The lower the number the higher the compatibility
Fluoroelastomer FKM
EPDM rubber
in
am
yl
op
es
an
h
et
n
xa
he
pr
clo
en
iso
Di
Cy
nz
Be
er
Figure 1
m
ro
lo
ch
Di
th
le
hy
et
Di
Z569941
10/30 joints
Z569968
14/20 joints, 2, 4, and 8 oz Aldrich bottles
Z569976 15/25 joints, 10, 32, 40 oz, 1 L Aldrich bottles,
125 mL, 1 L Sure/Seal bottles
Z569984
24/40 joints, 64, 80 oz, and 1 gal Aldrich jugs
4500
4000
3500
3000
2500
2000
1500
1000
500
0
27
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Aldrich

The new Aldrich Handbook contains the widest

Haydn Boehm, Ph. D.

Dear Fellow Chemists,

Dr. Haydn Boehm

Figure 1. Structure of Potassium carbobenzyloxycyanamide.

The reaction of amines with an activated carbodiimide represents

L499994 potassium salt

Scheme 1: Applications of potassium benzyloxycarbonylcyanamide

Figure 2. Examples of amine guanidinylation with potassium carbobenzyloxycyanamide.

5-Ethyl-2-methylpyridine borane (PEMB)

Select Substrate Scope

Excellent for reductive aminations

Can be used solvent-free for reductive aminations

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PEMB is a liquid Pyridine Borane Complex

For more examples and experimental detail

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