225649

Trimethylsilyl trifluoromethanesulfonate

99%

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

Properties

• Quality Level: 200
• assay: 99%
• form: liquid
• refractive index: n20/D 1.36 (lit.)
• bp: 77 °C/80 mmHg (lit.)
• density: 1.228 g/mL at 25 °C (lit.)
• 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

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.

Safety Information

• pictograms: GHS02,GHS05
• signalword: Danger
• hcodes: H226,H314
• pcodes: P210 - P233 - P240 - P280 - P303 + P361 + P353 - P305 + P351 + P338
• Hazard Classifications: Flam. Liq. 3 - Skin Corr. 1B
• supp_hazards: EUH014
• Storage Class: 3 - Flammable liquids
• wgk_germany: WGK 3
• flash_point_f: 77.0 °F - closed cup
• flash_point_c: 25 °C - closed cup
• ppe: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter