Synonyms: TMS triflate; TMSOTf; Trifluoromethanesulfonic acid trimethylsilylester
CAS Number: 27607-77-8
Formula: C4H9F3O3SSi
Formula Weight: 222.26
Linear Formula: CF3SO3Si(CH3)3
MDL No.: MFCD00000406
Purity: 0.99
Boiling Point: 77 C/80 mmHg(lit.)
Density: 1.228 g/mL at 25 C(lit.)
Refractive Index: n20/D 1.36(lit.)
Beilstein Registry Number: 1868911
EC Number: 248-565-4
UNSPSC Code: 12352000
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-L-daunosamine derivatives.
RIDADR: UN 2920 3(8) / PGII
WGK Germany: 3
Flash Point(F): 77 F
Flash Point(C): 25 C
R Codes: 12706
S Codes: 16-26-36/37/39-45
IOD Codes: C
Symbol: GHS02, GHS05
Signal Word: Danger
Hazard Statements: H226-H314
Precautionary statements: P280-P305 + P351 + P338-P310