225649

Trimethylsilyl trifluoromethanesulfonate

99%

• 동의어(들): TMS triflate, TMSOTf, Trifluoromethanesulfonic acid trimethylsilylester
• Linear Formula: CF₃SO₃Si(CH₃)₃
• CAS Number: 27607-77-8
• Molecular Weight: 222.26
• Beilstein: 1868911
• EC Number: 248-565-4
• MDL number: MFCD00000406
• UNSPSC 코드: 12352103
• PubChem Substance ID: 24853510
• NACRES: NA.22

속성

• Quality Level: 200
• 분석: 99%
• 양식: liquid
• refractive index: n20/D 1.36 (lit.)
• bp: 77 °C/80 mmHg (lit.)
• density: 1.228 g/mL at 25 °C (lit.)
• 작용기: fluoro; triflate
• SMILES string: 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
• InChI key: FTVLMFQEYACZNP-UHFFFAOYSA-N

설명

애플리케이션

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.[1][2]
It can be used:

• As a silylating agent for the synthesis of trimethylsilyl-enol ethers from esters of α-diazoacetoacetic acid.[3]
• To activate benzyl and allyl ethers for the alkylation of sulfides.[4]
• To facilitate the conversion of Diels-Alder adducts of Danishefsky′s diene to cyclohexenones without the formation of methoxy ketone by-product.[5]
• To prepare difluoroboron triflate etherate, a powerful Lewis acid especially in acetonitrile solvent.[6]
• As a reagent in a Dieckmann-like cyclization of ester-imides and diesters.[7]

It may also be used to catalyze:

• Acylation of alcohols with acid anhydrides.[8]
• Reductive coupling of carbonyl compounds with trialkylsilanes to form symmetrical ethers.[9]
• Glycosidation of 4-demethoxydaunomycinones with 1-O-acyl-L-daunosamine derivatives.[10]

안전성 정보

• 픽토그램: GHS02,GHS05
• 신호어: Danger
• 유해 및 위험 성명서: H226,H314
• 예방조치 성명서: P210 - P233 - P240 - P280 - P303 + P361 + P353 - P305 + P351 + P338
• Hazard Classifications: Flam. Liq. 3 - Skin Corr. 1B
• 보충제 위험성: EUH014
• Storage Class Code: 3 - Flammable liquids
• WGK: WGK 3
• Flash Point (°F): 77.0 °F - closed cup
• Flash Point (°C): 25 °C - closed cup
• 개인 보호 장비: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter