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225649 Aldrich

Trimethylsilyl trifluoromethanesulfonate

99%

Synonym: TMS triflate, TMSOTf, Trifluoromethanesulfonic acid trimethylsilylester

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Properties

Related Categories Chemical Synthesis, Protecting and Derivatizing Reagents, Protection and Derivatization, Silicon-Based, Synthetic Reagents More...
InChI Key   FTVLMFQEYACZNP-UHFFFAOYSA-N
assay   99%
refractive index   n20/D 1.36(lit.)
bp   77 °C/80 mmHg(lit.)
density   1.228 g/mL at 25 °C(lit.)

Description

Packaging

10, 50 g in ampule

250 g in glass bottle

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.<REFERENCE ID="81136" TYPE="literature"/>
• As a reagent in a Dieckmann-like cyclization of ester-imides and diesters.<REFERENCE ID="81137" TYPE="literature"/>

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 & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
Supplemental Hazard Statements 
Reacts violently with water.
RIDADR 
UN 2920 3(8) / PGII
WGK Germany 
3
Flash Point(F) 
77 °F
Flash Point(C) 
25 °C

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Protocols & Articles

Articles

Activating Reagents and Protecting Groups

The use of activating agents and protecting groups in organic synthesis is necessary to prevent unwanted side reactions from occurring when using other common reagents such as oxidizing or reducing a...
Chemfiles Volume 1 Article 3
Keywords: Organic synthesis

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