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T80489

Sigma-Aldrich

Trimethylsulfonium iodide

98%

Synonym(s):

Trimethyl-λ[3]-sulfane hydroiodide, Trimethylsulphonium iodide

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About This Item

Linear Formula:
(CH3)3S(I)
CAS Number:
2181-42-2
Molecular Weight:
204.07
Beilstein:
3555192
EC Number:
218-555-4
MDL number:
MFCD00011632
UNSPSC Code:
12352101
PubChem Substance ID:
24900497
NACRES:
NA.22

Assay

98%

reaction suitability

reaction type: C-C Bond Formation

mp

215-220 °C (lit.)

SMILES string

[I-].C[S+](C)C

InChI

1S/C3H9S.HI/c1-4(2)3;/h1-3H3;1H/q+1;/p-1

InChI key

VFJYIHQDILEQNR-UHFFFAOYSA-M

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General description

Trimethylsulfonium iodide is commonly used as a methylating agent in organic synthesis.

Application

Treatment with strong base yields the dimethylsulfonium methylide which reacts in-situ with the carbonyl group of ketones to form epoxides or allylic alcohols.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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K Müller et al.
Journal of clinical microbiology, 36(9), 2477-2480 (1998-08-15)
The MIDI automated Microbial Identification System (MIS) uses gas chromatography (GC) analysis of whole-cell fatty acid methyl esters (FAMEs) between 9 and 20 carbons in length to characterize a wide range of bacterial genera and species, including mycobacteria. Mycolic acid
Julien Dron et al.
Journal of chromatography. A, 1047(1), 111-116 (2004-10-16)
A procedure for the determination of fatty acids (FA) and glycerol in oils has been developed. The method includes a derivatization step of the FAs into their methyl esters or a transesterification of the triacylglycerols with trimethylsulfonium hydroxide (TMSH), respectively.
J L Hoffman
Journal of chromatography, 588(1-2), 211-216 (1991-12-27)
The use of single-column ion chromatography with conductometric detection was shown to be useful for the analysis of sulfonium and selenonium ions. A Hamilton PRP X-200 cation column was eluted with either solvent A (5 mM nitric acid in 30%
Synthesis, 404-404 (1987)
Yasuyuki Ishida et al.
Journal of chromatography. A, 1216(15), 3296-3299 (2009-02-19)
Reaction efficiencies of two organic alkalis, tetramethylammonium hydroxide (TMAH) and trimethylsulfonium hydroxide (TMSH), with lipids during thermally assisted hydrolysis and methylation (THM) were examined focusing on (1) the types of lipids and (2) degree of unsaturation of fatty acid moieties.
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