Trimethylsulfoxonium iodide

Trimethylsulfoxonium iodide is an organosulfur compound with the chemical formula [(CH₃)₃S=O]⁺I⁻. It is a sulfoxonium salt derived from dimethylsulfoxide. It is iodide salt of a common sulfoxonium cation. This compound, a colorless solid, is commercially available. It may be prepared by the alkylation of dimethyl sulfoxide with iodomethane:^[1]

(CH₃)₂SO + CH₃I → [(CH₃)₃SO]⁺I⁻

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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 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL283149 N
ChemSpider	67079 N
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 N Key: BPLKQGGAXWRFOE-UHFFFAOYSA-M N
SMILES O=[S+](C)(C)C.[I-]
Properties
Chemical formula	[(CH3)3SO]I
Molar mass	220.07 g·mol−1
Appearance	Colorless solid
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). N verify (what is YN ?) Infobox references

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The trimethylsulfoxonium ion features a tetrahedral molecular geometry at sulfur center. The ion has idealized C_3v symmetry. It is isoelectronic with trimethylphosphine oxide.

Trimethylsulfoxonium iodide is used to generate dimethyloxosulfonium methylide by reaction with sodium hydride.^[2] The latter compound is used to prepare epoxides from ketones and aldehydes.