225649

Trimethylsilyl trifluoromethanesulfonate

99%

• Synonyme(s) : TMS triflate, TMSOTf, Trifluoromethanesulfonic acid trimethylsilylester
• Formule linéaire : CF₃SO₃Si(CH₃)₃
• Numéro CAS: 27607-77-8
• Poids moléculaire : 222.26
• Numéro Beilstein : 1868911
• Numéro CE : 248-565-4
• Numéro MDL: MFCD00000406
• Code UNSPSC : 12352103
• ID de substance PubChem : 24853510
• Nomenclature NACRES : NA.22

Propriétés

• Niveau de qualité: 200
• Pureté: 99%
• Forme: liquid
• Indice de réfraction: n20/D 1.36 (lit.)
• Point d'ébullition: 77 °C/80 mmHg (lit.)
• Densité: 1.228 g/mL at 25 °C (lit.)
• Chaîne 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
• Clé InChI: FTVLMFQEYACZNP-UHFFFAOYSA-N

Description

Application

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.

Informations sur la sécurité

• Pictogrammes: GHS02,GHS05
• Mention d'avertissement: Danger
• Mentions de danger: H226,H314
• Conseils de prudence: P210 - P233 - P240 - P280 - P303 + P361 + P353 - P305 + P351 + P338
• Classification des risques: Flam. Liq. 3 - Skin Corr. 1B
• Risques supp: EUH014
• Code de la classe de stockage: 3 - Flammable liquids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): 77.0 °F - closed cup
• Point d'éclair (°C): 25 °C - closed cup
• Équipement de protection individuelle: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter