trimethylsulfanium iodide

• ChemBase ID: 52564
• Molecular Formular: C3H9IS
• Molecular Mass: 204.07303
• Monoisotopic Mass: 203.94696929
• SMILES: [S+](C)(C)C.[I-]
• Canonical SMILES: C[S+](C)C.[I-]
• InChI: InChI=1S/C3H9S.HI/c1-4(2)3;/h1-3H3;1H/q+1;/p-1
• InChIKey: VFJYIHQDILEQNR-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: trimethylsulfanium iodide
• IUPAC Traditional name: trimethylsulfonium iodide
• Synonyms: Trimethylsulfonium iodide; Trimethylsulfonium iodide; 三甲基碘化锍

Database IDs

• CAS Number: 2181-42-2
• EC Number: 218-555-4
• MDL Number: MFCD00011632
• Beilstein Number: 3555192
• PubChem SID: 24900497; 162057327
• PubChem CID: 75127

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): -0.07723071
• LogD (pH = 7.4): -0.07723071
• Log P: -0.07723071
• Molar Refractivity: 22.4031 cm^3
• Polarizability: 9.693327 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 213°C(sub); 215-220 °C(lit.); ca 215°C subl.

Safety Information

• Storage Warning: IRRITANT; Light Sensitive
• RTECS: WR8750000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (AT); 98%; 99%
• Grade: purum
• Linear Formula: (CH3)3S(I)

DETAILS

Sigma Aldrich - T80489

Packaging
25, 100 g in poly bottle
Application
Treatment with strong base yields the dimethylsulfonium methylide which reacts in-situ with the carbonyl group of ketones to form epoxides1 or allylic alcohols.2

Sigma Aldrich - 92762

Other Notes
Precursor of dimethylsulfonium methylide (methylene transfer reagent)1,2; Transformation of carbonyl compounds into epoxides or allylic alcohols3,4,5

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).