Trimethylsulfoxonium iodide

Product Name:

Trimethylsulfoxonium iodide

Synonyms:

sulfonium,trimethyl-,iodide,oxide;Sulfoxonium,trimethyl-,iodide;trimethyl-sulfoxoniuiodide;trimethylsulphoxoniumioidie;RARECHEM AQ A1 0066;TRIMETHYLSULFOXONIUM IODIDE;TRIMETHYLSULPHOXONIUM IODIDE;TMSOI

CAS:

1774-47-6

MF:

C3H9IOS

MW:

220.07

EINECS:

217-204-2

Product Categories:

Iodonium Sulfonium & Oxonium Compounds;Sulfonium Compounds;Sulfur Compounds (for Synthesis);Synthetic Organic Chemistry;Sulfonium/Sulfoxonium Compounds;Organic Building Blocks;Sulfur Compounds;Sulfonium/Sulfoxonium Compounds;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfur Compounds;Pharmaceutical Intermediates;Pyridines

Mol File:

1774-47-6.mol

Melting point 

208-212 °C (dec.)(lit.)

solubility 

H₂O: 50 mg/mL, clear

Water Solubility 

15 g/L (20 ºC)

Sensitive 

Light Sensitive

BRN 

3595854

CAS DataBase Reference

1774-47-6(CAS DataBase Reference)

EPA Substance Registry System

Sulfoxonium, trimethyl-, iodide(1774-47-6)

Chemical Properties

WHITE TO LIGHT YELLOW CRYSTALLINE POWDER

Uses

Treatment with strong base yields the ylide which adds to the carbonyl group of ketones1 and aldehydes2,3 to give epoxides. Also adds preferentially to the double bond of α,β-unsaturated esters to give cyclopropyl esters.4,5

Uses

Trimethylsulfoxonium Iodide is used to synthesize methylene-transfer reagents that are used in the preparation of epoxides.

Uses

Trimethylsulfoxonium iodide is a sulfoxonium salt. It is used to generate dimethyloxosulfonium methylide by reaction with sodium hydride. The latter compound is used as a methylene-transfer reagent, and is used to prepare epoxides.