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
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.
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
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
C Díez et al.
Journal of chromatography. A, 1125(2), 244-253 (2006-06-20)
In this study, an orthogonal array design was applied to know the way different parameters affected the derivatization of some herbicides that are commonly applied in the soils. Herbicides formulated as esters have been reported to rapidly hydrolyse, in contact
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