Trimethylsulfoxonium iodide

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Trimethylsulfoxonium iodide
Skeletal formulas of the trimethylsulfoxonium cation and the iodide anion
Space-filling models of the component ions of trimethylsulfoxonium iodide
IUPAC name
S,S,S-Trimethylsulfoxonium iodide
Other names
Trimethylsulphoxonium iodide; Trimethyloxosulfonium iodide
3D model (Jmol)
ECHA InfoCard 100.015.641
EC Number 217-204-2
Molar mass 220.07 g·mol−1
Melting point 208 to 212 °C (406 to 414 °F; 481 to 485 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Trimethylsulfoxonium iodide is a sulfoxonium salt. It is used to generate dimethyloxosulfonium methylide by reaction with sodium hydride.[1] The latter compound is used as a methylene-transfer reagent, and is used to prepare epoxides.

This compound is commercially available. It may be prepared by the reaction of dimethyl sulfoxide and iodomethane:[2]

(CH3)2SO + CH3I → (CH3)3SO+I


  1. ^ E. J. Corey1 and Michael Chaykovsky2. "Methylenecyclohexane Oxide". Org. Synth. ; Coll. Vol., 5, p. 755 
  2. ^ Lampman, Gary M.; Koops, Roger W.; Olden, Caroline C. (1985). "Phosphorus and sulfur ylide formation: Preparation of 1-benzoyl-2-phenylcyclopropane and 1,4-diphenyl-1,3-butadiene by phase transfer catalysis". J. Chem. Ed. 62 (3): 267. doi:10.1021/ed062p267.