Trimethylsilyl trifluoromethanesulfonate
Trimethylsilyl trifluoromethanesulfonate (CAS 27607-77-8), commonly called TMS triflate or TMSOTf and listed with EC number 248-565-4, is a colourless to pale yellow liquid and one of the most reactive silylating agents available, supplied at 99 percent purity. It is strongly moisture sensitive and corrosive, fuming in humid air and hydrolysing rapidly to hexamethyldisiloxane and trifluoromethanesulfonic acid, so it must be stored under inert gas in a sealed container away from water. The combination of the trimethylsilyl cation with the extremely weakly coordinating triflate anion produces a powerful Lewis acid and a highly electrophilic silicon centre. The reagent is soluble in chlorinated and ethereal solvents used for anhydrous synthesis, and it is a standard tool in carbohydrate, nucleoside and complex natural product chemistry.
1. Lewis acid catalyst: catalyses glycosylation, aldol, Michael, Diels-Alder, Friedel-Crafts and rearrangement reactions and promotes the activation of esters, oximes, nitro compounds, ketones and acetals in demanding synthetic sequences.
2. Silylating agent: converts alcohols, amines, thiols and enolisable carbonyls into trimethylsilyl ethers, enol ethers and silyl amines, and is widely used for protective-group installation and for generating reactive intermediates in situ.
3. Glycochemistry and pharmaceutical process chemistry: a standard promoter for stereoselective glycosidic bond formation in carbohydrate, nucleoside, antiviral and anticancer compound manufacture, and a reagent in oligonucleotide synthesis.
4. Handling and storage: highly corrosive and moisture sensitive; handle in a glovebox or under inert gas, store sealed and dry with a desiccant, use anhydrous solvents and protective equipment, and quench spills carefully because acidic vapours are released.
Product Name: Trimethylsilyl trifluoromethanesulfonate
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