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Methanethiol

Methanethiol /ˈmɛθeɪnˈθaɪɒl/ (also known as methyl mercaptan) is an


Methanethiol
organosulfur compound with the chemical formula CH3SH. It is a
colorless gas with a distinctive putrid smell. It is a natural substance
found in the blood and brain of humans and animals, as well as in plant
tissues. It is disposed of through animal feces. It also occurs naturally in
certain foods, such as some nuts and cheese. It is one of the main
compounds responsible for bad breath and the smell of flatus.
Methanethiol is classified as a thiol and is sometimes abbreviated as
MeSH. It is very flammable.

Contents
Structure and reactions Names
Occurrence Preferred IUPAC name
Preparation Methanethiol
Uses Other names
Safety Methyl mercaptan
References Mercaptomethane
External links Methiol
Thiomethyl alcohol
Methylthiol
Structure and reactions Identifiers

The molecule is tetrahedral at carbon, like methanol. It is a weak acid,


CAS Number 74-93-1
with a pKa of ~10.4, but is about a million times more acidic than 3D model (JSmol) Interactive image
methanol. The colorless salt can be obtained in this way:
ChEBI CHEBI:16007
CH3SH + CH3ONa → CH3SNa + CH3OH ChemSpider 855 [chemspiders]

The resulting thiolate anion is a strongnucleophile. ECHA InfoCard 100.000.748


KEGG C00409
It can be oxidized to dimethyl disulfide:
UNII 2X8406WW9I
2CH3SH + [O] → CH3SSCH3 + H2O
InChI
Further oxidation takes the disulfide to methanesulfonic acid, which is SMILES
odorless. Bleach deodorizes methanethiol in this way.
Properties
Chemical formula CH3SH
Occurrence
Molar mass 48.11 g·mol−1
MeSH is released as a by-product of kraft pulping in pulp mills. In kraft
Appearance colorless gas[1]
pulping, lignin is depolymerized by nucleophilic attack with the strongly
Odor Rotten cabbage,
nucleophilic hydrosulfide ion (HS−) in a highly alkaline medium.
flatulence
However, in a side reaction, HS− attacks methoxyl groups (OMe) in
Density 0.9 g/mL (liquid at 0°C)[1]
lignin, demethylating them to give free phenolate groups (PhO−) and Melting point −123 °C (−189 °F; 150 K)
releasing MeSH. Due to alkalinity, MeSH is readily deprotonated
Boiling point 5.95 °C (42.71 °F;
(MeSNa), and the formed MeS− ion is also a strong nucleophile, reacting
279.10 K)
further to dimethyl sulfide. The compounds remain in the black liquor
Solubility in water 2%
and are burned in the recovery boiler, where the sulfide is recovered as
sodium sulfide.[3] Solubility alcohol, ether
Vapor pressure 1.7 atm (20°C)[1]
Methanethiol is released from decaying organic matter in marshes and is
present in the natural gas of certain regions, in coal tar, and in some crude Acidity (pKa) ~10.4
oils. It occurs in various plants and vegetables, such as radishes. Hazards
EU classification
In surface seawater, methanethiol is the primary breakdown product of (DSD) (outdated) F+ T
the algal metabolite dimethylsulfoniopropionate(DMSP). Marine bacteria
N
appear to obtain most of the sulfur in their proteins by the breakdown of
DMSP and incorporation of methanethiol, despite the fact that R-phrases R12, R23, R50/53
methanethiol is present in seawater at much lower concentrations than (outdated)

sulfate (~0.3 nM vs. 28 mM). Bacteria in environments both with and S-phrases S16, S25, S33S60, S61
without oxygen can also convert methanethiol todimethyl sulfide (DMS), (outdated)
although most DMS in surface seawater is produced by a separate NFPA 704
pathway. Both DMS and methanethiol can be used by certain microbes as 4
substrates for methanogenesis in some anaerobic soils. 4 1
Methanethiol is a byproduct of the metabolism of asparagus.[4] The
ability to produce methanethiol in urine after eating asparagus was once Flash point −18 °C; 0 °F; 255 K [1]
thought to be a genetic trait. More recent research suggests that the Explosive limits 3.9%-21.8%[1]
peculiar odor is in fact produced by all humans after consuming Lethal dose or concentration (LD, LC):
asparagus, while the ability to detect it (methanethiol being one of many
LD50 (median 60.67 mg/kg (mammal)[2]
components in "asparagus pee") is in fact the genetic trait.[5] The dose)
chemical components responsible for the change in the odor of urine
[6]
LC50 (median 3.3 ppm (mouse, 2 hr)
show as soon as 15 minutes after eating asparagus. concentration) 675 ppm (rat, 4 hr)[2]
US health exposure limits (NIOSH):
Preparation PEL C 10 ppm (20 mg/m3)[1]
Methanethiol is prepared commercially by the reaction of methanol with (Permissible)
hydrogen sulfide gas over an acidic solid catalyst, such asalumina:[7] REL C 0.5 ppm (1 mg/m3) [15-
(Recommended) minute][1]
CH3OH + H2S → CH3SH + H2O
IDLH 150 ppm[1]
(Immediate
Although impractical, it can be prepared by the reaction of methyl iodide danger)
with thiourea.[8]
Related compounds
Related Ethanethiol
Uses compounds
Hydrogen sulfide
Methanethiol is mainly used to produce methionine, which is used as a
dietary component in poultry and animal feed.[7] Methanethiol is also Except where otherwise noted, data are given
for materials in their standard state (at 25 °C
used in the plastic industry as a moderator for free-radical
[77 °F], 100 kPa).
polymerizations[7] and as a precursor in the manufacture ofpesticides.
verify (what is ?)
Mercaptan is also used in the natural gas industry as an odorant, due to its Infobox references
ideal compatibility with methane. Its characteristic "rotten eggs" smell is
widely known by natural gas customers as an indicator of a possible gas
leak, even a very minute one.[9]
Safety
The safety data sheet (SDS) lists methanethiol as a colorless, flammable gas with an
extremely strong and repulsive smell. At very high concentrations it is highly toxic
and affects the central nervous system. Its penetrating odor provides warning at
dangerous concentrations. An odor threshold of 1 ppb has been reported.[10] The
United States OSHA Ceiling Limit is listed as 10 ppm.

A severe methyl mercaptan leak killed four employees and injured another in a
DuPont facility in La Porte, Texas, near Houston, on 15 November 2014.[11]

References
1. "NIOSH Pocket Guide to Chemical Hazards #0425"(https://www.cdc.go
v/niosh/npg/npgd0425.html). National Institute for Occupational Safety
and Health (NIOSH).
2. "Methyl mercaptan" (https://www.cdc.gov/niosh/idlh/74931.html).
Immediately Dangerous to Life and Health Concentrations (IDLH) .
National Institute for Occupational Safety and Health(NIOSH).
3. Sixta, H.; Potthast, A.; Krotschek, A. W., Chemical Pulping Processes.
In Handbook of Pulp, Sixta, H., Ed. Wiley-VCH V erlag GmbH & Co.: Cylinder of methanethiol gas
Weinheim, 2006; Vol. 1, p 169 (109-510).
4. Richer, Decker, Belin, Imbs, Montastruc, Giudicelli:"Odorous urine in
man after asparagus" (http://www.pubmedcentral.nih.gov/articlerender.fc
gi?artid=1379934), British Journal of Clinical Pharmacology, May 1989
5. Lison M, Blondheim SH, Melmed RN (1980)."A polymorphism of the
ability to smell urinary metabolites of asparagus"(https://www.ncbi.nlm.n
ih.gov/pmc/articles/PMC1715705). Br Med J. 281 (6256): 1676–8.
doi:10.1136/bmj.281.6256.1676(https://doi.org/10.1136%2Fbmj.281.62
56.1676). PMC 1715705 (https://www.ncbi.nlm.nih.gov/pmc/articles/PM
C1715705) . PMID 7448566 (https://www.ncbi.nlm.nih.gov/pubmed/744
8566).
6. Skinny On: Discovery Channel(http://www.discovery.com/area/skinnyo
n/skinnyon970115/skinny1.html)Archived (https://web.archive.org/web/2
0080229081018/http://www.discovery.com/area/skinnyon/skinnyon9701
15/skinny1.html) 2008-02-29 at the Wayback Machine.
7. Norell, John; Louthan, Rector P. (1988). "Thiols". Kirk-Othmer Concise
Encylclopedia of Chemical Technology (3rd ed.). New York: John Wiley
& Sons, Inc. pp. 946–963.ISBN 978-0471801047.
8. Reid, E. Emmet (1958).Organic Chemistry of Bivalent Sulfur. 1. New
York: Chemical Publishing Company, Inc. pp. 32–33, 38.
9. SafeGase: About Natural Gas:(http://www.safegas.org/about/about.htm
l)
10. Devos, M; F. Patte; J. Rouault; P. Lafort; L. J. Van Gemert (1990).
Standardized Human Olfactory Thresholds. Oxford: IRL Press. p. 101.
ISBN 0199631468.
11. HazMat Management Magazine article:(http://www.hazmatmag.com/ha
zmat/four-dupont-workers-suffocated-methyl-mercaptan-leak-texas/1003
272774/)

External links
NLM Hazardous Substances Databank – Methyl mercaptan
CDC - NIOSH Pocket Guide to Chemical Hazards

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