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T80489

Sigma-Aldrich

Trimethylsulfonium iodide

98%

Sinónimos:

Trimethyl-λ[3]-sulfane hydroiodide, Trimethylsulphonium iodide

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About This Item

Fórmula lineal:
(CH3)3S(I)
Número de CAS:
2181-42-2
Peso molecular:
204.07
Beilstein/REAXYS Number:
3555192
EC Number:
218-555-4
MDL number:
MFCD00011632
UNSPSC Code:
12352101
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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

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

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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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