Trimethylsilyl trifluoromethanesulfonate
ALDRICH/225649 - 99%
Synonym: TMS triflate; TMSOTf; Trifluoromethanesulfonic acid trimethylsilylester
CAS Number: 27607-77-8
Empirical Formula (Hill Notation): C4H9F3O3SSi
Molecular Weight: 222.26
EC Number: 248-565-4
MDL Number: MFCD00000406
Linear Formula: CF3SO3Si(CH3)3
Product Type: Chemical
| assay | 99% |
| bp | 77 °C/80 mmHg (lit.) |
| density | 1.228 g/mL at 25 °C (lit.) |
| form | liquid |
| functional group | fluoro |
| triflate | |
| InChI | 1S/C4H9F3O3SSi/c1-12(2,3) |
| InChI key | FTVLMFQEYACZNP-UHFFFAOYSA |
| Quality Level | 200  |
| refractive index | n |
| SMILES string | C[Si](C)(C)OS(=O)(=O)C(F) |
| 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- |
| Packaging: | 10, 50 g in ampule |
| Packaging: | 250 g in glass bottle |
| Symbol |   GHS02,GHS05 |
| Signal word | Danger |
| Hazard statements | H226 - H314 |
| Precautionary statements | P210 - P233 - P240 - P280 - P303 + P361 + P353 - P305 + P351 + P338 |
| Hazard Codes | C |
| Risk Statements | 10-14-34 |
| Safety Statements | 16-26-36/37/39-45 |
| RIDADR | UN 2920 3(8) / PGII |
| WGK Germany | WGK 3 |
| Flash Point(F) | 77.0 °F - closed cup |
| Flash Point(C) | 25 °C - closed cup |
| Supplemental Hazard Statements | EUH014 |
| Purity | 99% |
| bp | 77 °C/80 mmHg (lit.) |
| Density | 1.228 g/mL at 25 °C (lit.) |
| Refractive Index | n |
| UNSPSC | 12352103 |