225649

Trimethylsilyl trifluoromethanesulfonate

99%

• Sinónimos: TMS triflate, TMSOTf, Trifluoromethanesulfonic acid trimethylsilylester
• Fórmula lineal: CF₃SO₃Si(CH₃)₃
• Número de CAS: 27607-77-8
• Peso molecular: 222.26
• Beilstein: 1868911
• Número CE: 248-565-4
• Número MDL: MFCD00000406
• Código UNSPSC: 12352103
• ID de la sustancia en PubChem: 24853510
• NACRES: NA.22

Propiedades

• Nivel de calidad: 200
• Ensayo: 99%
• Formulario: liquid
• índice de refracción: n20/D 1.36 (lit.)
• bp: 77 °C/80 mmHg (lit.)
• densidad: 1.228 g/mL at 25 °C (lit.)
• grupo funcional: fluoro; triflate
• cadena SMILES: C[Si](C)(C)OS(=O)(=O)C(F)(F)F
• InChI: 1S/C4H9F3O3SSi/c1-12(2,3)10-11(8,9)4(5,6)7/h1-3H3
• Clave InChI: FTVLMFQEYACZNP-UHFFFAOYSA-N

Descripción

Aplicación

Trimethylsilyl trifluoromethanesulfonate has been used in combination with boron trifluoride etherate for the copper-catalyzed asymmetric allylic alkylation (AAA) of allyl bromides, chlorides, and ethers with organolithium reagents in the presence of a chiral ligand.
It can be used:

• As a silylating agent for the synthesis of trimethylsilyl-enol ethers from esters of α-diazoacetoacetic acid.
• To activate benzyl and allyl ethers for the alkylation of sulfides.
• To facilitate the conversion of Diels-Alder adducts of Danishefsky′s diene to cyclohexenones without the formation of methoxy ketone by-product.
• To prepare difluoroboron triflate etherate, a powerful Lewis acid especially in acetonitrile solvent.
• As a reagent in a Dieckmann-like cyclization of ester-imides and diesters.

It may also be used to catalyze:

• Acylation of alcohols with acid anhydrides.
• Reductive coupling of carbonyl compounds with trialkylsilanes to form symmetrical ethers.
• Glycosidation of 4-demethoxydaunomycinones with 1-O-acyl-L-daunosamine derivatives.

Información de seguridad

• Pictogramas: GHS02,GHS05
• Palabra de señalización: Danger
• Frases de peligro: H226,H314
• Consejos de prudencia: P210 - P233 - P240 - P280 - P303 + P361 + P353 - P305 + P351 + P338
• Clasificaciones de peligro: Flam. Liq. 3 - Skin Corr. 1B
• Riesgos supl.: EUH014
• Código de clase de almacenamiento: 3 - Flammable liquids
• Clase de riesgo para el agua (WGK): WGK 3
• Punto de inflamabilidad (°F): 77.0 °F - closed cup
• Punto de inflamabilidad (°C): 25 °C - closed cup
• Equipo de protección personal: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter