Trimethylsulfonium iodide

• Catalog No.: A12639
• CAS Number: 2181-42-2
• M. F.: C3H9IS
• M. W.: 204.07303
• Purity: 99%

SYNONYMS

• Title: 三甲基碘化锍
• IUPAC name: trimethylsulfanium iodide
• IUPAC Traditional name: trimethylsulfonium iodide

DATABASE IDS

• CAS Number: 2181-42-2
• EC Number: 218-555-4
• Beilstein Number: 3555192
• MDL Number: MFCD00011632

PROPERTIES

• Purity: 99%
• Melting Point: ca 215°C subl.
• GHS Hazard statements: H315-H319-H335
• European Hazard Symbols: Irritant (Xi)
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Risk Statements: 36/37/38
• RTECS: WR8750000
• Safety Statements: 26-37
• Storage Warning: Light Sensitive
• TSCA Listed: 是

REFERENCES

• Methylene transfer to imines and arylhydrazones gives aziridines and N-arylaminoaziridines respectively: Synthesis, 330 (1983).
• The ylide, generated with strong base, is a powerful methylene transfer reagent, converting aldehydes and ketones to epoxides; reaction with ɑ?-enones also gives epoxides (contrast Trimethylsulfoxonium iodide, A14589): J. Am. Chem. Soc., 87, 1353 (1965):
  
• Other conditions for addition to aldehydes include: phase-transfer catalysis: Angew. Chem. Int. Ed., 12, 845 (1973), KOH in acetonitrile: Tetrahedron Lett., 23, 5283 (1982), or KF on alumina: Tetrahedron, 41, 1259 (1985). With aryl aldehydes, the use of KO-t-Bu gives improved results by suppressing the competing Cannizzaro reaction: Org. Prep. Proced. Int., 27, 219 (1995). A simplified, solvent-free method employing KO-t-Bu has been reported for ketones: Heterocycles, 46, 185 (1997). With excess of the sulfonium ylide, ketones or epoxides give good yields of allylic alcohols, whereas aldehydes give poor yields. Under similar conditions, the sulfoxonium ylide gives oxetanes: Tetrahedron Lett., 35, 2009, 5449 (1994).
• Addition to vinyl sulfones gives cyclopropyl sulfones: J. Org. Chem., 29, 3277 (1964). Similarly, vinylsulfonates and sulfonamides give cyclopropanes in fair to good yields: J. Org. Chem., 33, 3849 (1968).
• Methylene transfer to allylic, propargylic, benzylic and primary alkyl halides and sulfonates results in formation of terminal alkenes in generally good yields: Tetrahedron Lett., 35, 5453 (1994).
• Reaction with Ag₂O gives the corresponding hydroxide, which is a useful methylating agent for various functional groups, including carboxylic acids, phenols, thiols and N-heterocycles: J. Org. Chem., 44, 638 (1979). Both the iodide and the hydroxide have been used for the methylation of pyrimidine nucleosides; see, e.g.: J. Chem. Soc., Perkin 1, 13 (1989).