DI-TERT-BUTYLSILYL BIS(TRIFLUOROMETHANESULFONATE) Chemical Properties

Boiling point:

73-75 °C/0.35 mmHg (lit.)

Density 

1.352 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.398(lit.)

Flash point:

195 °F

storage temp. 

Inert atmosphere,Room Temperature

solubility 

sol most common organic solvents.

form 

Oil

color 

Clear Pale Yellow

Specific Gravity

1.358

Hydrolytic Sensitivity

8: reacts rapidly with moisture, water, protic solvents

BRN 

3569211

Stability:

Moisture Sensitive

InChIKey

HUHKPYLEVGCJTG-UHFFFAOYSA-N

CAS DataBase Reference

85272-31-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-36/37/39-45

RIDADR 

UN 3265 8/PG 2

WGK Germany 

3

F 

10-21

Hazard Note 

Corrosive

TSCA 

No

HazardClass 

8

PackingGroup 

III

HS Code 

29319090

MSDS

• Language:English Provider:SigmaAldrich

DI-TERT-BUTYLSILYL BIS(TRIFLUOROMETHANESULFONATE) Usage And Synthesis

Chemical Properties

Colorless to yellow liquid

Physical properties

bp 73–75°C/0.35 mmHg; d 1.208 g cm?3.

Uses

Protecting group reagent for 1,3-diols used recently in a synthesis of N-homoceramides. Also used for selective α-galactosylation in the synthesis of α-galactosyl ceramides.

Uses

Di-t-butylsilyl bis(trifluoromethanesulfonate) is a reagent for the selective protection of polyhydroxy compounds. This reagent reacts with 1,2-, 1,3-, and 1,4-diols under mild conditions to give the corresponding dialkylsilylene derivatives in high yield (0–50°C, 79–96%). Deprotection is conveniently achieved by using aqueous hydrofluoric acid in acetonitrile (eq 1).
Unlike di-t-butyldichlorosilane, this reagent reacts with hindered alcohols. Even pinacol reacts to give the silylene derivative (100°C, 24 h, 70%). Di-t-butylsilylene derivatives of 1,2-diols are more reactive than those of 1,3- and 1,4-diols and undergo rapid hydrolysis (5 min) in THF/H2O at pH 10, while the 1,3- and 1,4- derivatives are unaffected at pH 4–10 (22°C) for several hours. This protecting group is stable under the conditions of PDC oxidation of alcohols (CH2Cl2, 25?C, 27 h) and tosylation of alcohols (pyridine, 25°C, 27 h).
The reagent has seen limited use for the protection of alcohols but has been used to protect nucleosides (eq 2).The procedure consists of sequential addition of the ditriflate and triethylamine to the nucleoside in DMF. The choice of solvent is critical.

Preparation

by the treatment of di-t-butylchlorosilane with trifluoromethanesulfonic acid, followed by distillation (71% yield).

DI-TERT-BUTYLSILYL BIS(TRIFLUOROMETHANESULFONATE)(85272-31-7)Related Product Information

• Isobutylamine
• 2,4,6-Triisopropylbenzenesulfonyl chloride
• Trifluoromethane
• Trifluoromethanesulfonic acid
• DIISOPROPYLSILANE
• DI-TERT-BUTYLSILYL BIS(TRIFLUOROMETHANESULFONATE)
• DIISOPROPYLSILYL BIS(TRIFLUOROMETHANESULFONATE)
• DIMETHYLBIS(TRIFLUOROMETHYLSULFONYLOXY)SILANE
• DI-TERT-BUTYLSILANE