Trimethylsilyl trifluoromethanesulfonate CAS#27607-77-8

CAS Number: 27607-77-8
Chemical Formula: C4H9F3O3SSi
Synonyms:

TRIMETHYLSILYL TRIFLUOROMETHANESULPHONATE
CT3795
Methanesulfonic acid, trifluoro-, trimethylsilyl ester

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Product Details

Trimethylsilyl trifluoromethanesulfonate CAS#27607-77-8

Trimethylsilyl Trifluoromethane sulfonate is generally used following reactions:
1. Silylation. TMSOTf is widely used in the conversion of car bonyl compounds to their enol ethers. The conversion is some 109 faster with TMSOTf/triethylamine than with chlorotrimethy lsilane.Dicarbonyl compounds are converted to the corresponding bis enol ethers; this method is an improvement over the previous two step method.In general, TMSOTf has a tendency toC-silylation which is seen most clearly in the reaction of esters, whereC-silylation dominates over O-silylation.
2.Carbonyl Activation. 1,3-Dioxolanation of conjugated enals is facilitated by TMSOTf in the presence of 1,2-bis(trimethylsilyl oxy)ethane. In particular, highly selective protection of sterically differentiated ketones is possible (eq 10).TMSOTf mediates a stereoselective aldol-type condensation of silyl enol ethers and acetals (or orthoesters). The nonbasic reaction conditions are extremely mild. The use of TMSOTf in aldol reactions of silyl enol ethers and ketene acetals with aldehydes is ubiquitous. Stereoselective cyclization of α,β-unsaturated enamide esters is induced by TMSOTf and has been used as a route to quinolizidines and indolizidines.

Trimethylsilyl trifluoromethanesulfonate Chemical Properties

Melting point	25°C
Boiling point	77 °C/80 mmHg (lit.)
density	1.228 g/mL at 25 °C (lit.)
vapor pressure	4.7 hPa (20 °C)
refractive index	n20/D 1.36(lit.)
Fp	78 °F
storage temp.	Store below +30°C.
solubility	sol aliphatic and aromatic hydrocarbons, haloalkanes, ethers.
form	Fuming Liquid
color	Clear colorless to light brown
Specific Gravity	1.15
Water Solubility	REACTS
Sensitive	Moisture Sensitive
Hydrolytic Sensitivity	8: reacts rapidly with moisture, water, protic solvents
Merck	14,9719
BRN	1868911
InChIKey	FTVLMFQEYACZNP-UHFFFAOYSA-N
CAS DataBase Reference	27607-77-8(CAS DataBase Reference)
NIST Chemistry Reference	Trimethylsilyl trifluoromethanesulfonate(27607-77-8)
EPA Substance Registry System	Methanesulfonic acid, trifluoro-, trimethylsilyl ester (27607-77-8)

Safety Information

Hazard Codes	C,F
Risk Statements	10-14-34
Safety Statements	16-26-36/37/39-45-8
RIDADR	UN 2920 8/PG 2
WGK Germany	3
F	10-21
Autoignition Temperature	405 °C DIN 51794
Hazard Note	Corrosive/Flammable
TSCA	TSCA listed
HazardClass	3
PackingGroup	III
HS Code	29310095

Product Application of Trimethylsilyl trifluoromethanesulfonate CAS#27607-77-8

Trimethylsilyl Trifluoromethanesulfonate is a trialkylsilyl triflate used as a catalyst in organic synthesis. Trimethylsilyl Trifluoromethanesulfonate is used in combination with boron trifluoride eth yl ether to prepare a Lewis acid that is more powerful than its components and especially effective in acetonitrile solvent. Trimethylsilyl is a common reagent used in a Dieckmann-like cyclization of ester-imides and diesters.

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