Trifluoromethanesulfonic acid tert-butyldimethylsilyl ester Property

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H226Flammable liquid and vapour

H314Causes severe skin burns and eye damage

H335May cause respiratory irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Trifluoromethanesulfonic acid tert-butyldimethylsilyl ester Chemical Properties,Usage,Production

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.