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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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H Castejon et al.
Journal of the American Chemical Society, 123(25), 6092-6097 (2001-06-21)
The reaction of ammonia and pyridine with trimethylsulfonium ion has been studied in gas phase and solution. Density functional theory at the B3LYP/6-31+G level was used to describe the energy changes along the reaction coordinate in the gas phase, and
Jörg Schönherr
Pest management science, 58(4), 343-351 (2002-04-27)
Penetration of glyphosate salts across isolated poplar (Populus canescens (Aiton) Sm) cuticular membranes (CM) was studied using Na+, K+, NH4+, trimethylsulfonium+ (TMS) and isopropylamine+ (IPA) as cations. After droplet drying, humidity over the salt residues on the outer surfaces of
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.
Tetrahedron Letters, 35, 2009-2009 (1994)
K D Müller et al.
Zentralblatt fur Bakteriologie : international journal of medical microbiology, 274(2), 174-182 (1990-11-01)
Gas-liquid chromatography of cellular fatty acids is a useful tool for the identification of bacteria. Derivatization of bacterial fatty acids to methyl esters by conventional techniques is usually time-consuming and complicated. A new one-step technique using trimethyl-sulfonium hydroxide allows the
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