Trimethylsulfonium hydroxide

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Structural formula
Structural formula of TMSH OH - ion
General
Surname Trimethylsulfonium hydroxide
other names

TMSH

Molecular formula C 3 H 10 OS
External identifiers / databases
CAS number 17287-03-5
EC number 628-493-3
ECHA InfoCard 100.156.758
PubChem 11105313
Wikidata Q1559354
properties
Molar mass 94.18 g mol −1
safety instructions
GHS labeling of hazardous substances

for the ~ 0.25 M solution in methanol

02 - Highly / extremely flammable 06 - Toxic or very toxic 08 - Dangerous to health

danger

H and P phrases H: 225-301-311-315-319-331-370
P: 210-260-280-301 + 310-305 + 351 + 338-311
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Trimethylsulfonium hydroxide is a sulfonium compound with hydroxide as an anion .

use

TMSH serves as a methylation reagent and is therefore one of the alkylating agents , which also explains the toxicity of the substance.

In gas chromatography , TMSH is used to convert certain groups of substances into their methylated derivatives so that their volatility increases. For example, carboxylic acid esters such as triglycerides are converted into their methyl esters by transesterification and free carboxylic acids by esterification . Also alcohols , thiols , and N- heterocyclic compounds can be reacted with trimethylsulfonium too easy chromatographable products. The reaction takes place at room temperature, but can be completed by brief heating to approx. 100 ° C, which is a prerequisite for quantitative evaluations. Dimethyl sulfide is formed as a by-product in reactions of this type .

Individual evidence

  1. ↑ a b Data sheet Trimethylsulfonium hydroxide solution, ~ 0.25 M in methanol, for GC derivatization from Sigma-Aldrich , accessed on May 19, 2017 ( PDF ).
  2. ↑ Parts of the labeling of hazardous substances relate to the hazards caused by the solvent.
  3. ↑ E. Schulte, K. Weber: Fast production of fatty acid methyl esters from fats with trimethylsulfonium hydroxide or sodium methylate. Lipid - Fett 1989, 91 (5), 181-183, doi : 10.1002 / lipi.19890910504 .
  4. ↑ Kumar Deb Mukherjee, Nikolaus Weber: Analysis of lipids. CRC Press 1993, ISBN 0-8493-3039-4 ( Limited preview in Google Book Search), p. 141.