Description

tert-Butyl(diphenyl)silyl trifluoromethanesulphonate (CAS No. 92886-86-7) is a highly specialized organosilicon reagent with the molecular formula C₁₇H₁₉F₃O₃SSi. This compound is widely recognized for its role as a silylating agent in organic synthesis, particularly in the protection of hydroxyl groups and other nucleophilic functionalities. Its robust tert-butyldiphenylsilyl (TBDPS) group offers superior steric protection, making it ideal for selective derivatization in complex molecular architectures. The trifluoromethanesulfonate (triflate) leaving group enhances reactivity, enabling efficient silyl transfer under mild conditions. Suitable for anhydrous and inert environments, this reagent is supplied as a high-purity solid, ensuring consistent performance in sensitive synthetic applications such as peptide chemistry, carbohydrate modification, and pharmaceutical intermediate synthesis. Store under nitrogen or argon at recommended temperatures to maintain stability.

Properties

• CAS Number: 92886-86-7
• Complexity: 519
• IUPAC Name: [tert-butyl(diphenyl)silyl] trifluoromethanesulfonate
• InChI: InChI=1S/C17H19F3O3SSi/c1-16(2,3)25(14-10-6-4-7-11-14,15-12-8-5-9-13-15)23-24(21,22)17(18,19)20/h4-13H,1-3H3
• InChI Key: AOMOJFWVOHXBTN-UHFFFAOYSA-N
• Exact Mass: 388.07762666
• Molecular Formula: C17H19F3O3SSi
• Molecular Weight: 388.5
• SMILES: CC(C)(C)[Si](C1=CC=CC=C1)(C2=CC=CC=C2)OS(=O)(=O)C(F)(F)F
• Topological: 51.8
• Monoisotopic Mass: 388.07762666
• Synonyms: tert-Butyl(diphenyl)silyl trifluoromethanesulphonate, 640-683-8, tert-Butyldiphenylsilyl Trifluoromethanesulfonate, 92886-86-7, [tert-butyl(diphenyl)silyl] trifluoromethanesulfonate, tert-Butyldiphenylsilyl Triflate, MFCD01941212, tert-ButyldiphenylsilylTrifluoromethanesulfonate, C17H19F3O3SSi, SCHEMBL537975, DTXSID10449421, AOMOJFWVOHXBTN-UHFFFAOYSA-N, AKOS015853177, Methanesulfonic acid, trifluoro-, (1,1-dimethylethyl)diphenylsilyl ester, TERT-BUTYLDIPHENYLSILYL TRIFLATE), BS-18252, DB-234016, B2898, CS-0154940, t-butyldiphenylsilyl trifluoromethane sulfonate, C77182, Trifluoromethanesulfonic Acid tert-Butyldiphenylsilyl Ester

Application

tert-Butyl(diphenyl)silyl trifluoromethanesulphonate is primarily employed as a protecting group reagent for alcohols and phenols in multistep organic synthesis. Its sterically demanding TBDPS group provides excellent selectivity in the presence of other functional groups, making it indispensable in the synthesis of natural products and complex drug molecules. The triflate moiety ensures rapid activation under mild conditions, facilitating efficient silylation even with hindered substrates. Common applications include the protection of sugar hydroxyls in carbohydrate chemistry and the temporary masking of reactive sites in peptide synthesis. Its stability under basic conditions allows for orthogonal deprotection strategies in tandem with other protecting groups.

Safety and Hazards

GHS Hazard Statements

• H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
• H318 (33.3%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

Precautionary Statements

• P260, P264, P264+P265, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P363, P405, and P501

Hazard Classes and Categories

• Skin Corr. 1C (100%)
• Eye Dam. 1 (33.3%)

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