Trimethylsilyl trifluoromethanesulfonate

• Catalog No.: A12535
• CAS Number: 27607-77-8
• M. F.: C4H9F3O3SSi
• M. W.: 222.2581696
• Purity: 99%

SYNONYMS

• Title: 三氟甲烷磺酸三甲基硅烷酯
• IUPAC name: trimethylsilyl trifluoromethanesulfonate
• IUPAC Traditional name: trimethylsilyl triflate
• Synonyms: TMS-OTf; Trifluoromethanesulfonic acid trimethylsilyl ester

DATABASE IDS

• CAS Number: 27607-77-8
• Beilstein Number: 1868911
• EC Number: 248-565-4
• MDL Number: MFCD00000406
• Merck Index: 149719

PROPERTIES

• Purity: 99%
• Boiling Point: 39-40°C/12mm
• Density: 1.225
• Flash Point: 25°C(77°F)
• Refractive Index: 1.3620
• GHS Hazard statements: H314-H318-H226
• European Hazard Symbols: Corrosive (C)
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A
• Risk Statements: 10-14-34
• Safety Statements: 8-20-26-30-36/37/39-45-60
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 3
• UN Number: UN2924
• Packing Group: III

REFERENCES

• Trialkylsilyl perfluoroalkanesulfonates are highly reactive silylating agents (see Appendix 4) and Lewis acids: Synthesis, 1 (1982); Adv. Silicon Chem., 1, 189 (1991).
• Amides can be N,O-disilylated with TMSOTf: Org. Synth. Coll., 9, 516 (1998). For conversion of carbonyl compounds to silyl enol ethers, see, e.g.: J. Org. Chem., 58, 1449 (1993); Org. Synth. Coll., 9, 548 (1998). The reaction rate in triethylamine is almost 10⁹ times faster than with TMS chloride: Liebigs Ann. Chem., 1718 (1980).
• In general, TMSOTf has a much greater tendency to give C-silylation than TMS chloride. With esters C-silylation usually predominates: Synthesis, 867 (1977); Liebigs Ann. Chem., 816 (1983). Nitriles are C-silylated: Synthesis, 636 (1977); Synth. Commun., 18, 2111 (1988). Electron-rich alkenes, e.g. ketene acetals, as well as electron-rich aromatics such as indoles and pyrroles also undergo C-silylation: Synthesis, 928, 929 (1984):
  
• tert-Butyl esters are cleaved directly to trimethylsilyl esters. Benzyl esters are unaffected, permitting selective cleavage: Synthesis, 545 (1980).
• TMSOTf has numerous applications as a Lewis acid catalyst, notably in mediating, under very mild conditions, crossed aldol condensations between silyl enol ethers and acetals: J. Am. Chem. Soc., 102, 3248 (1980); Tetrahedron, 44, 4259 (1988); Org. Synth. Coll., 9, 642 (1998).
• For a brief feature on uses of the reagent, see: Synlett, 1940 (2003).