Trimethylsilyl trifluoromethanesulfonate
TMS triflate
Trimethylsilyl trifluoromethanesulfonate (CF3SO3Si(CH3)3, MW 222.26) can be used to prepare a strong Lewis acid, difluoroboron triflate etherate, in acetonitrile.
- CAS No.
- 27607-77-8
- Molecular formula
- C4H9F3O3SSi
- Molecular weight
- 222.25 g/mol
- Purity
- On request
AppearanceClear slightly yellow liquid.
Price, specification and samples on request · reply within one working day
Made in our own plantsPanoli GIDC, Ankleshwar
Tested in our QC labHPLC · GC · KF and more
COA & SDSShared with every quotation
Grams to multi-tonnesSamples to commercial supply
Overview
It is used in Dieckmann-type cyclizations of ester-amides or diesters and to convert carbonyl compounds into enol ethers.
It is also used in chemical glycosylation and, because its reactivity resembles trimethylsilyl chloride, in general organic synthesis.
Applications
- Copper-catalyzed asymmetric allylic alkylation (AAA) of allyl bromides and chlorides, used with boron trifluoride etherate
- Silylating agent for preparing trimethylsilyl enol ethers of α-diazoacetic acid
- Activating benzyl and alkyl ethers for alkylation of sulfides
- Converting Diels-Alder adducts from Danishefsky's diene into cyclohexenones without forming the methoxy ketone byproduct
- Preparing difluoroboron triflate etherate, a strong Lewis acid, especially in acetonitrile
- Reagent in Dieckmann-like cyclization of ester-amides or esters
Technical specifications
| Boiling point | 140ºC |
|---|---|
| Flash Point | 25ºC |
| Density | 1.225 |
| Vapor Pressure | 2.22E-09mmHg at 25°C |
| Water Solubility | Reacts |
| Stability | Stable at room temperature in closed containers under normal storage and handling conditions. |
Packaging & storage
2-8ºC
Safety information
- H226: Flammable liquid and vapour.
- H314: Causes severe skin burns and eye damage.
Full details are in the Safety Data Sheet, sent with every quotation.