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T80489

Sigma-Aldrich

Trimethylsulfonium iodide

98%

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Synonym(s):
Trimethyl-λ[3]-sulfane hydroiodide, Trimethylsulphonium iodide
Linear Formula:
(CH3)3S(I)
CAS Number:
2181-42-2
Molecular Weight:
204.07
Beilstein:
3555192
EC Number:
218-555-4
MDL number:
MFCD00011632
PubChem Substance ID:
24900497
NACRES:
NA.22

Quality Level

200

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

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Facile access to S-methyl dithiocarbamates with sulfonium or sulfoxonium iodide as a methylation reagent
Deng H, et al.
Organic & Biomolecular Chemistry, 21(32), 6474-6478 (2023)
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
Bassam Lajin et al.
PloS one, 11(11), e0167013-e0167013 (2016-11-22)
Hydrogen sulfide is a signaling molecule that plays important roles in several physiological processes, and its methylation product trimethylsulfonium (TMS) is a natural constituent of human urine that could serve as a biomarker for hydrogen sulfide. In vitro studies showed
Lawrence Akoto et al.
Journal of chromatography. A, 1186(1-2), 365-371 (2007-09-25)
Gas chromatography (GC) has in recent times become an important tool for the fatty acid profiling of human blood and plasma. An at-line procedure used in the fatty acid profiling of whole/intact aquatic micro-organisms without any sample preparation was adapted
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%
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