tert-Butyldimethylsilyl trifluoromethanesulfonate

• Catalog No.: A12174
• CAS Number: 69739-34-0
• M. F.: C7H15F3O3SSi
• M. W.: 264.3379096
• Purity: 98%

SYNONYMS

• Title: 三氟甲烷磺酸叔丁基二甲基硅烷基酯
• IUPAC name: tert-butyldimethylsilyl trifluoromethanesulfonate
• IUPAC Traditional name: tert-butyldimethylsilyl trifluoromethanesulfonate
• Synonyms: tert-Butyldimethylsilyl Triflate; TBDMS-OTf

DATABASE IDS

• Beilstein Number: 2370068
• CAS Number: 69739-34-0
• MDL Number: MFCD00000405
• EC Number: 274-102-0

PROPERTIES

• Purity: 98%
• Boiling Point: 65-67°C/12mm
• Density: 1.151
• Flash Point: 36°C(96°F)
• Refractive Index: 1.3860
• 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: 10-34
• Safety Statements: 26-36/37/39-45
• Storage Warning: Moisture Sensitive
• TSCA Listed: 否
• Hazard Class: 8
• UN Number: UN2920
• Packing Group: II

REFERENCES

• Powerful silylating agent (see Appendix 4) and Lewis acid; compare tert-Butyldimethylchlorosilane, A13064 and 3429. Silylation of hindered alcohols can be effected with TBDMS-OTf and 2,6-lutidine, where other reagents are unsuccessful: Tetrahedron Lett., 22, 3455 (1981).
• Has been used in a sequence for the conversion of N-Boc to N-Cbz: Tetrahedron Lett., 26, 5543 (1985). For an alternative method for this transformation, see Benzyl 2,2,2-trichloroacetimidate, A12387.
• Treatment of ɑ?-unsaturated esters containing a suitably-placed ketone function with the reagent and triethylamine results in tandem intramolecular Michael-aldol reactions to give cyclobutanone derivatives: J. Am. Chem. Soc., 115, 8107 (1993).
• For general reactions of trialkylsilyl perfluoroalkanesulfonates, see Trimethylsilyl trifluoromethanesulfonate, A12535; reviews: Synthesis, 1 (1982); Adv. Silicon Chem., 1, 189 (1991).