T80489
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:
Molecular Weight:
204.07
Beilstein:
3555192
EC Number:
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
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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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
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)
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%
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.
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