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Trifluoromethanesulfonic acid tert-butyldimethylsilyl ester

Product NameTrifluoromethanesulfonic acid tert-butyldimethylsilyl ester

CAS69739-34-0

MFC7H15F3O3SSi

MW264.34

EINECS274-102-0

MOL File69739-34-0.mol

Chemical Properties

Melting point	<0°C
Boiling point	65-67 °C12 mm Hg(lit.)
Density	1.151 g/mL at 25 °C(lit.)
refractive index	n20/D 1.385(lit.)
Flash point	98 °F
storage temp.	2-8°C
solubility	Slightly miscible with chloroform.
form	Fuming Liquid
Specific Gravity	1.151
color	Clear colorless to yellow
Water Solubility	DECOMPOSES
Sensitive	Moisture Sensitive
Hydrolytic Sensitivity	8: reacts rapidly with moisture, water, protic solvents
BRN	2370068
InChIKey	WLLIXJBWWFGEHT-UHFFFAOYSA-N
CAS DataBase Reference	69739-34-0(CAS DataBase Reference)
NIST Chemistry Reference	Tert-butyldimethylsilyl trifluoromethanesulfonate(69739-34-0)

Safety Information

Hazard Codes	C,F
Risk Statements	10-34-37
Safety Statements	26-36/37/39-45-25-16
RIDADR	UN 2920 8/PG 2
WGK Germany	3
F	10-21
Hazard Note	Flammable/Corrosive
TSCA	No
HazardClass	3
PackingGroup	III
HS Code	29310095

MSDS

Usage And Synthesis

Chemical Properties

clear colorless to yellow fuming liquid
Physical properties

bp 60°C/7 mmHg; colorless oil, d 1.151 g cm?3. Solubility: sol most organic solvents such as pentane, CH2Cl2, etc.
Uses

TrifluoroMethanesulfonic acid tert-butyldiMethylsilyl ester is a highly reactive silylating agent and lewis acid capable of converting primary, secondary and tertiary alcohols to their respectctive TBDMS. TrifluoroMethanesulfonic acid tert-butyldiMethylsilyl ester is also used to covert ketones and lactones into their enol silyl ethers.
Uses

tert-Butyldimethylsilyl trifluoromethanesulfonate is involved in the introduction of a bulky tert-butyl dimethylsilyl group onto a cis-bis(alkenyl)oxirane used in Cope rearrangement. It is associated with a thiolane and promotes the chalcogenide-Morita-Baylis-Hillman reaction. Further, it is used as a highly reactive silylating agent. In addition to this, it is used to prepare enol silyl ethers by reacting with ketones and lactones.
Uses

t-Butyldimethylsilyl Trifluoromethanesulfonate is used as a highly reactive silylating agent and Lewis acid capable of converting primary, secondary, and tertiary alcohols1b to the corresponding TBDMS ethers, and converting ketones and lactones, into their enol silyl ethers; promoting conjugate addition of alkynylzinc compounds and triphenylphosphine5 to α,β-enones; activation of chromones in [4 + 2] cycloaddition reactions;rearrangement of allylic tributylstannyl silyl ethers; activation of pyridine rings toward Grignard reagents and transalkylation of tertiary amine N-oxides;and transformation of N-t-butoxycarbonyl groups into N-alkoxycarbonyl groups.
Preparation

to 24 g (0.16 mol) of t-butyldimethylchlorosilane at 23°C under argon is added 14 mL (0.16 mol) of trifluoromethanesulfonic acid dropwise. The solution is heated at 60°C for 10 h, at which time no further hydrogen chloride evolves (removed through a bubbler). The resulting product is distilled under reduced pressure: 34 g (80% yield) of TBDMS triflate; bp 60°C/7 mmHg.

Trifluoromethanesulfonic acid tert-butyldimethylsilyl ester

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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