TERT-BUTYL TRIMETHYLSILYLACETATE Chemical Properties

Boiling point:

67 °C13 mm Hg(lit.)

Density 

0.86 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.417

Flash point:

42 °C

solubility 

Chloroform (Soluble), Methanol (Soluble)

form 

Oil

color 

Colourless

BRN 

1930256

Safety Information

Risk Statements 

10

Safety Statements 

23-24/25

RIDADR 

UN 3272 3/PG 3

WGK Germany 

3

F 

10-21

HazardClass 

3.2

PackingGroup 

III

MSDS

• Language:English Provider:SigmaAldrich

TERT-BUTYL TRIMETHYLSILYLACETATE Usage And Synthesis

Physical properties

air stable, colorless liquid; bp 67°C/13 mmHg; n20 D 1.4184; 1H NMR (CDCl3, 90 MHz) 0.13 (s, 9H), 1.45 (s, 9H), 1.80 (s, 2H); IR 1710 cm?1.

Uses

t-Butyl Trimethylsilylacetate is used to prepare lithium enolates which can be alkylated;can be alkenated with aldehydes and ketones;can be acylated;can be reacted with Group 14 halides.
Most applications require initial formation of the enolate (1) (eq 1), which is obtained as a white solid suspended in THF, stable indefinitely at ?78°C.

Preparation

an advantage of t-butyl trimethylsilylacetate over its methyl and ethyl ester analogs is that it can be prepared by C-silylation of the lithium enolate of t-butyl acetate at ?78°C in THF (85–90% yield). Under the same conditions the enolates of methyl and ethyl acetate give primarily O-silylated products.The reagent has also been prepared by a rapid boron trifluoride etherate catalyzed reaction of trimethylsilylketene with t-butyl alcohol.

TERT-BUTYL TRIMETHYLSILYLACETATE(41108-81-0)Related Product Information

• (TRIMETHYLSILYL)ACETIC ACID
• METHYL (TRIMETHYLSILYL)ACETATE
• Ethyl (trimethylsilyl)acetate
• TERT-BUTYL TRIMETHYLSILYLACETATE
• TERT-BUTYL-2-CHLORO-2-TRIMETHYLSILYLACETATE
• 2-(Trimethylsilyl)ethanol