Trimethylsulfoxonium iodide
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.
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| Names | |
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| IUPAC name
S,S,S-Trimethylsulfoxonium iodide | |
| Other names
Trimethylsulphoxonium iodide; Trimethyloxosulfonium iodide | |
| Identifiers | |
3D model (JSmol) |
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.015.641  |
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| Properties | |
| 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). | |
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| Infobox references | |
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
- E. J. Corey1 and Michael Chaykovsky2. "Methylenecyclohexane Oxide". Organic Syntheses.; Collective Volume, 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.
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