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T80489

Trimethylsulfonium iodide

Name: Trimethylsulfonium iodide
Brand: ALDRICH

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%

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Properties

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

Description

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

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

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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A new and rapid method for the assay of bacterial fatty acids using high resolution capillary gas chromatography and trimethylsulfonium hydroxide.

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

Reaction efficiency of organic alkalis with various classes of lipids during thermally assisted hydrolysis and methylation.

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.

Tetrahedron Letters, 35, 2009-2009 (1994)

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