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Trimethylsulfonium iodide_Molecular_structure_CAS_2181-42-2)
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Trimethylsulfonium iodide

Catalog No. A12639 Name Alfa Aesar
CAS Number 2181-42-2 Website
M. F. C3H9IS Telephone
M. W. 204.07303 Fax
Purity 99% Email
Storage Chembase ID: 52564

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 Pictograms GHS07
GHS Hazard statements H315-H319-H335
European Hazard Symbols Irritant 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

DETAILS

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).