Trifluoromethanesulfonic acid tert-butyldimethylsilyl ester 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

Stability:

Moisture Sensitive

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

• Language:English Provider:Trifluoromethanesulfonic acid tert-butyldimethylsilyl ester
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Trifluoromethanesulfonic acid tert-butyldimethylsilyl ester 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

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.

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

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.

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(69739-34-0)Related Product Information

• Trifluoromethanesulfonic acid
• TERT-BUTYL VINYL ETHER
• Butylated hydroxyanisole
• tert-Butyldimethylsilyl chloride
• tert-Butylchlorodiphenylsilane
• TERT-BUTYLDIMETHYL(2-PROPYNYLOXY)SILANE
• Trifluoromethanesulfonic anhydride
• Trifluoroacetic anhydride
• TERT-BUTYL PROPIOLATE
• Trifluoromethanesulfonic acid difluoromethyl ester
• TERT-BUTYLMETHOXYPHENYLSILYL BROMIDE
• 2-Methyl-N-(thiophen-2-ylMethyl)propan-2-aMine
• tert-Butyldiphenylsilane
• tert-Butyl(3-fluorophenoxy)dimethylsilane
• Trifluoromethanesulfonic acid tert-butyldimethylsilyl ester
• ETHYLDIMETHYLSILANE
• T-BUTYLDIMETHYLSILANE
• Trifluoromethane