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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Synthesis, 404-404 (1987)
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.
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
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
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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