Description

Trimethylsilyl triflate (CAS No. 27607-77-8) is a highly reactive organosilicon compound with the molecular formula C₄H₉F₃O₃SSi. Also known as trimethylsilyl trifluoromethanesulfonate, this versatile reagent is widely used as a powerful silylating agent and Lewis acid catalyst in organic synthesis. Its strong affinity for oxygen and nitrogen nucleophiles makes it ideal for protecting group chemistry, glycosylation reactions, and the activation of inert functional groups. The compound is moisture-sensitive and typically handled under inert conditions. Available in high-purity grades, our Trimethylsilyl triflate is rigorously tested for quality, ensuring optimal performance in demanding research applications.

Properties

• CAS Number: 27607-77-8
• Complexity: 244
• IUPAC Name: trimethylsilyl trifluoromethanesulfonate
• InChI: InChI=1S/C4H9F3O3SSi/c1-12(2,3)10-11(8,9)4(5,6)7/h1-3H3
• InChI Key: FTVLMFQEYACZNP-UHFFFAOYSA-N
• Exact Mass: 221.99937634
• Molecular Formula: C4H9F3O3SSi
• Molecular Weight: 222.26
• SMILES: C[Si](C)(C)OS(=O)(=O)C(F)(F)F
• Topological: 51.8
• Monoisotopic Mass: 221.99937634
• Synonyms: Trimethylsilyl trifluoromethanesulfonate, 27607-77-8, Trimethylsilyl triflate, Trimethylsilyl trifluoromethanesulphonate, Trimethylsilyl trifluoromethylsulfonate, Methanesulfonic acid, trifluoro-, trimethylsilyl ester, UNII-Z84V0CBH9J, Z84V0CBH9J, trimethylsilyltriflate, EINECS 248-565-4, trimethylsilyltrifluoromethane sulfonate, trimethylsilanol trifluoromethanesulfonate, DTXSID2067325, TRIMETHYLSILYL TRIFLATE [MI], 1,1,1-Trifluoromethanesulfonic acid trimethylsilyl ester, TMS-TFMS, DTXCID8037704, 248-565-4, TMSOTf, trimethylsilyltrifluoromethanesulfonate, Trifluoromethanesulfonic acid trimethylsilyl ester, TMS triflate, trimethylsilyl trifluoromethylsulphonate, Methanesulfonic acid, 1,1,1-trifluoro-, trimethylsilyl ester, Trimethylsilyl trifluromethanesulfonate, Trimethylsilyltrifluoromethylsulfonate, trimethylsilyltrifluoromethanesulphonate, trimethylsilyl trifluoromethane sulfonate, Trimethylsilyl trifluoromethanesulfonate, 99%, C4H9F3O3SSi, trifluoromethansulfonic acid trimethylsilyl ester, TMStriflate, TMS-triflate, TMSOTf cpd, Me3SiOTf, trimethylsilyltriflat, trimethylsilyltrifiate, MFCD00000406, trimethysilyl triflate, TMS-OTf, trimethylsilyl-triflate, Me3SiOSO2CF3, Me3SiOSO2 CF3, CF3SO2OSi(CH3)3, SCHEMBL28527, 22607-77-8, BCP33650, CS-B0886, trimethylsilyltrifluorometansulphonate, trimethysilyltrifluoromethanesulfonate, trimethylsilyl trifluorometanesulfonate, trimethylsilyl trifluoromethansulfonate, trimethylsilyl-trifluoromethansulfonate, AKOS005063796, trimethylsilyl-trifluoromethanesulfonate, trimethylsilyltrifluoromethane-sulfonate, FT03406, SB40866, trifluoromethylsulfonyloxytrimethylsilane, trifluoromethanesulfonyloxytrimethylsilane, Trimethyl-silyl trifluoromethanesulfonate, trimethylsilyl trifluoro-methane sulfonate, trimethylsilyl trifluoromethane sulphonate, trimethylsilyl trifluoromethane-sulphonate, AS-40538, trifluoromethane-sulfonyloxytrimethylsilane, trimethylsilyltrifluoromethanesulfonic acid, trimethyl-silyl trifluoro-methane sulfonate, DB-009881, NS00049524, T0871, EN300-37509, A819133, Trifluoromethane sulphonic acid trimethylsilyl ester, Q15427958, F8880-4610, Trimethylsilyl trifluoromethanesulfonate, packed in ampule, Trimethylsilyl trifluoromethanesulfonate, purum, >=98.0% (T), Trimethylsilyl triflate;TMSOTf;Trimethylsilyl trifluoromethanesulphonate, Trimethylsilyl trifluoromethanesulfonate, produced by Wacker Chemie AG, Burghausen, Germany, >=98.0% (T)

Application

Trimethylsilyl triflate is extensively used in organic synthesis as a catalyst for glycosylation reactions, enabling the formation of complex carbohydrate structures. It serves as a potent silylating agent for the protection of alcohols, amines, and other nucleophilic functional groups. The compound is also employed in the activation of carbonyl compounds and the synthesis of silicon-containing intermediates. Its strong Lewis acidity makes it valuable in polymerization and rearrangement reactions.

Safety and Hazards

GHS Hazard Statements

• H226 (92.1%): Flammable liquid and vapor [Warning Flammable liquids]
• H314 (93.7%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

Precautionary Statements

• P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P321, P363, P370+P378, P403+P235, P405, and P501

Hazard Classes and Categories

• Flam. Liq. 3 (92.1%)
• Skin Corr. 1B (93.7%)

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