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Sigma Aldrich Trimethylsilyl Trifluoromethanesulfonate

Catalog No. 22564950G Shop All MilliporeSigma Sigma Organic Chemistry Products
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MilliporeSigma Sigma Organics products encompass a wide range of quality reagents, solvents, catalysts, and building blocks for organic synthesis. From benchtop discovery to process development and scale-up, Sigma Organics solutions are built to meet the needs of synthetic chemists.

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 +a-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.

Specifications

CAS 27607-77-8
Density 1.228 g/mL at 25°C
Boiling Point 77°C80 mmHg, lit.)
Molecular Formula C4H9F3O3SSi
Refractive Index n20/D 1.36
Linear Formula CF3SO3Si(CH3)3
MDL Number MFCD00000406
Quantity 50 g
Synonym TMS triflate; TMSOTf; Trifluoromethanesulfonic acid trimethylsilylester
Molecular Weight (g/mol) 222.26 g/mol
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