Trimethylsulfoxonium iodide

Trimethylsulfoxonium iodide
Names
	Preferred IUPAC name Trimethyl(oxo)-λ4-sulfanium iodide
	Other names Trimethylsulphoxonium iodide; Trimethyloxosulfonium iodide; S,S,S-Trimethylsulfoxonium iodide
Identifiers
CAS Number	1774-47-6 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL283149 ;
ChemSpider	67079 ;
ECHA InfoCard	100.015.641
EC Number	217-204-2;
PubChem CID	74498;
CompTox Dashboard (EPA)	DTXSID001014581 ;
	InChI InChI=1S/C3H9OS.HI/c1-5(2,3)4;/h1-3H3;1H/q+1;/p-1 Key: BPLKQGGAXWRFOE-UHFFFAOYSA-M ;
	SMILES O=[S+](C)(C)C.[I-];
Properties
Chemical formula	C3H9IOS
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). verify (what is ?) 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⁻

References

^ Corey, E. J.; Chaykovsky, Michael. "Methylenecyclohexane Oxide". Organic Syntheses; Collected Volumes, vol. 5, p. 755.
^ 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. Educ. 62 (3): 267. Bibcode:1985JChEd..62..267L. doi:10.1021/ed062p267.