Triethylsilyl trifluoromethanesulfonate Chemical Properties

Boiling point:

85-86 °C/12 mmHg (lit.)

Density 

1.169 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.389(lit.)

Flash point:

162 °F

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Triethylsilyl Trifluoromethanesulfonate is readily sol hydrocarbons, dialkyl ethers, halogenated solvents. CH2Cl2 is employed most commonly. Reactions in 1,2-dichloroethane proceed faster than those in CCl4 or Et2O. Protic solvents and THF react with trialkylsilyl triflates and are therefore not suitable.

form 

Fuming Liquid

Specific Gravity

1.169

color 

Clear colorless to light brown

Water Solubility 

Miscible with dichloromethane, hydrocarbons, dialkyl ethers and halogenated solvents. Immiscible with water.

Sensitive 

Moisture Sensitive

Hydrolytic Sensitivity

8: reacts rapidly with moisture, water, protic solvents

BRN 

3590541

Stability:

Moisture Sensitive and Hygroscopic, Moisture Sensitive And Hygroscopic

CAS DataBase Reference

79271-56-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

C,F

Risk Statements 

34-14

Safety Statements 

26-36/37/39-45-27

RIDADR 

UN 3265 8/PG 2

WGK Germany 

3

F 

10-21

Hazard Note 

Corrosive/Flammable

TSCA 

No

HazardClass 

8

PackingGroup 

II

HS Code 

29319090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Triethylsilyl trifluoromethanesulfonate Usage And Synthesis

Chemical Properties

clear colorless to light brown fuming liquid

Physical properties

85–86 °C/12 mmHg; d 1.169 g cm?3.

Uses

Triethylsilyl Trifluoromethanesulfonate can be used as potent silylating agent and as Lewis acid catalyst. Triethylsilyl ethers are generally more stable towards hydrolysis than are trimethylsilyl ethers, and consequently the Et3Si moiety has gained increasing use as a protecting group for alcohols. However, since it is often difficult to silylate sterically hindered hydroxyl groups using Et3SiCl, triethylsilyl perchlorate and triethylsilyl triflate (Et3SiOTf) were introduced to overcome this problem. Jefford has reported that condensation reactions of 2-trimethylsiloxyfuran with aldehydes can be catalyzed by Et3SiOTf to give mainly the threo addition product (eq 8).

Uses

Triethylsilyl trifluoromethanesulfonate acts as a silylating agent. It is also useful as a Lewis acid catalyst. Further, it reacts with 1-diazo-3,3-dimethyl-butan-2-one to prepare 1-diazo-3,3-dimethyl-1-(triethylsilyl)-2-butanone.

Preparation

Triethylsilyl Trifluoromethanesulfonate can be prepared by reacting chlorotriethylsilane with trifluoromethanesulfonic acid followed by distillation.

Triethylsilyl trifluoromethanesulfonate(79271-56-0)Related Product Information

• Gabexate mesylate
• Trifluoromethanesulfonic acid
• COPPER(II) TRIFLUOROMETHANESULFONATE
• YTTERBIUM(III) TRIFLUOROMETHANESULFONATE HYDRATE
• Pefloxacin mesylate
• Lithium trifluoromethanesulfonate
• Levofloxacin Methylate
• Danofloxacin mesylate
• Scandium trifluoromethanesulfonate
• Sodium trifluoromethanesulfonate
• Trifluoromethanesulfonic anhydride
• Triethylsilane
• Triethylene glycol dimethacrylate
• TRIISOPROPYLSILYL ACRYLATE
• triisopropylsilyl Methacrylate
• Sodium methanesulfinate
• Trifluoromethane
• Hydrogen Sulfide