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Merck
CN

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:
2181-42-2
Molecular Weight:
204.07
UNSPSC Code:
12352101
NACRES:
NA.22
PubChem Substance ID:
24900497
EC Number:
218-555-4
Beilstein/REAXYS Number:
3555192
MDL number:
MFCD00011632
Assay:
98%

Key Documents

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Product Name

Trimethylsulfonium iodide, 98%

InChI key

VFJYIHQDILEQNR-UHFFFAOYSA-M

InChI

1S/C3H9S.HI/c1-4(2)3;/h1-3H3;1H/q+1;/p-1

SMILES string

[I-].C[S+](C)C

assay

98%

reaction suitability

reaction type: C-C Bond Formation

mp

215-220 °C (lit.)

Quality Level

200

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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.

General description

Trimethylsulfonium iodide is commonly used as a methylating agent in organic synthesis.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
1425114
11709KO
11714CH
11614CH
01513BH

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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
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.
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%
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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