Triisopropylsilyl trifluoromethanesulfonate

• Catalog No.: B21127
• CAS Number: 80522-42-5
• M. F.: C10H21F3O3SSi
• M. W.: 306.4176496
• Purity: 97%

SYNONYMS

• Title: 三异丙基甲硅烷基三氟甲烷磺酸盐
• IUPAC name: tris(propan-2-yl)silyl trifluoromethanesulfonate
• IUPAC Traditional name: triisopropylsilyl trifluoromethanesulfonate
• Synonyms: Trifluoromethanesulfonic acid triisopropylsilyl ester; TIPS-OTf

DATABASE IDS

• MDL Number: MFCD00009913
• CAS Number: 80522-42-5
• EC Number: 000-000-0
• Beilstein Number: 3591541

PROPERTIES

• Purity: 97%
• Boiling Point: 45-46°C/0.03mm
• Density: 1.136
• Flash Point: 100°C(212°F)
• Refractive Index: 1.4150
• GHS Hazard statements: H314-H318
• European Hazard Symbols: Corrosive (C)
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A
• Risk Statements: 34
• Safety Statements: 26-36/37/39-45
• Storage Warning: Moisture Sensitive
• TSCA Listed: 否
• Hazard Class: 8
• UN Number: UN3265
• Packing Group: II

REFERENCES

• Reagent for introduction of the triisopropylsilyl (TIPS) group: Tetrahedron Lett., 22, 3455 (1981); compare Chlorotriisopropylsilane, A17376, and Appendix 4. For general reactions of silyl triflates, see Trimethylsilyl trifluoromethanesulfonate, A12535.
• For use in the synthesis of 2-substituted benzothiopyran-4-ones, see: Synlett, 182 (1996):
  
• A method for protecting both H atoms of a primary amine consists of formation of the succinimide, followed by enolsilylation with TIPS-OTf, to form the 2,5-bis(triisopropylsiloxy)pyrroles. Deprotection can be effected by desilylation with dilute HCl, followed by hydrazinolysis: Tetrahedron Lett., 38, 2617 (1997).
• For a comprehensive review of the TIPS group in organic chemistry, see: Chem. Rev., 95, 1009 (1995).