Description

Triisopropylsilyl trifluoromethanesulfonate (CAS No. 80522-42-5) is a highly reactive silylating agent with the molecular formula C₁₀H₂₁F₃O₃SSi. This organosilicon compound is widely utilized in organic synthesis as a robust protecting group reagent, particularly for alcohols and other nucleophiles. Its trifluoromethanesulfonate (triflate) group enhances its reactivity, making it an excellent choice for silylation under mild conditions. The triisopropylsilyl (TIPS) group provides steric bulk, ensuring selective protection in complex molecular environments. This reagent is supplied as a high-purity liquid, ideal for sensitive reactions in pharmaceutical, agrochemical, and materials science research. Store under inert conditions to maintain stability and reactivity.

Properties

• CAS Number: 80522-42-5
• Complexity: 347
• IUPAC Name: triisopropylsilyl trifluoromethanesulfonate
• InChI: InChI=1S/C10H21F3O3SSi/c1-7(2)18(8(3)4,9(5)6)16-17(14,15)10(11,12)13/h7-9H,1-6H3
• InChI Key: LHJCZOXMCGQVDQ-UHFFFAOYSA-N
• Exact Mass: 306.09327672
• Molecular Formula: C10H21F3O3SSi
• Molecular Weight: 306.42
• SMILES: CC(C)[Si](C(C)C)(C(C)C)OS(=O)(=O)C(F)(F)F
• Topological: 51.8
• Monoisotopic Mass: 306.09327672
• Synonyms: Triisopropylsilyl trifluoromethanesulfonate, 80522-42-5, DTXSID10369150, DTXCID70320186, 638-988-6, Triisopropylsilyl triflate, Trifluoromethanesulfonic acid triisopropylsilyl ester, triisopropylsilyltrifluoromethanesulfonate, triisopropylsilyl trifluoromethanesulphonate, triisopropylsilyl-trifluoromethanesulfonate, tri(propan-2-yl)silyl trifluoromethanesulfonate, TIPS triflate, Triisopropylsilyl trifluoromethanesulfonate, 97%, tris(propan-2-yl)silyl trifluoromethanesulfonate, tips-otf, MFCD00009913, TIPSOTf; Triisopropyl(trifluoromethanesulfonato)silane; Triisopropylsilyl Triflate; TIPS Triflate; 1,1,1-Trifluoromethanesulfonic Acid Tris(1-methylethyl)silyl Ester, TIPSOTf, i-Pr3SiOTf, (i-Pr)3SiOTf, triisopropylsilyltriflate, Methanesulfonic acid, trifluoro-, tris(1-methylethyl)silyl ester, triisopropylsilanyl triflate, R7C8KB3N7A, C10H21F3O3SSi, SCHEMBL114743, CS-B0888, AKOS008901285, FS-4750, FT31908, triisopropylsilyl trifluoromethylsulfonate, triisopropylsilyltrifluoromethanesulphonate, triisopropylsilyl-trifluoromethyl sulfonate, triisopropylsilyltrifluoromethane sulfonate, triisopropysilyl trifluoromethane-sulfonate, triisopropysilyl trifluoromethanesulphonate, Triisopropylsilyl trifluoromethane sulfonate, triisopropylsilyl trifluoromethane-sulfonate, triisopropylsilyl-trifluoro-methanesulfonate, triisopropylsilyl-trifluoromethane sulfonate, Triisopropylsilyltrifluoromethane sulphonate, DB-056444, tri-isopropylsilyl trifluoromethane sulfonate, Triisopropyl(trifluoromethanesulfonato)silane, T1588, tri-iso-propylsilyl trifluoromethane sulfonate, EN300-6762257, tris(1-methylethyl)silyl trifluoromethanesulfonate, Trifluoromethanesulfonic acid triisopropylsilyl ester;TIPS triflate;Triisopropylsilyl triflate

Application

Triisopropylsilyl trifluoromethanesulfonate is primarily used as a protecting group reagent for hydroxyl groups in carbohydrate and steroid chemistry. It enables selective silylation of primary alcohols in the presence of secondary or tertiary alcohols due to its steric hindrance. The compound is also employed in nucleoside and peptide synthesis, where temporary protection of reactive sites is critical. Its triflate leaving group facilitates efficient silyl transfer in mild conditions, minimizing side reactions. Researchers value it for its compatibility with a wide range of functional groups in complex synthetic pathways.

Safety and Hazards

GHS Hazard Statements

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

Precautionary Statements

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

Hazard Classes and Categories

• Skin Corr. 1B (100%)

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