DIMETHYLKETENE METHYL TRIMETHYLSILYL ACETAL Chemical Properties

Boiling point:

35 °C15 mm Hg(lit.)

Density 

0.858 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.415(lit.)

Flash point:

58 °F

storage temp. 

Inert atmosphere,Room Temperature

solubility 

freely sol organic solvents.

form 

clear liquid

color 

Colorless to Almost colorless

Specific Gravity

0.858

Water Solubility 

Hydrolyzes in water.

Sensitive 

Moisture Sensitive

Hydrolytic Sensitivity

8: reacts rapidly with moisture, water, protic solvents

BRN 

1362893

Stability:

Moisture and Acid Sensitive

CAS DataBase Reference

31469-15-5(CAS DataBase Reference)

EPA Substance Registry System

Silane, [(1-methoxy-2-methyl-1-propenyl)oxy]trimethyl- (31469-15-5)

Safety Information

Hazard Codes 

Xi

Risk Statements 

10-36/37/38

Safety Statements 

16-26-36

RIDADR 

UN 3271 3/PG 3

WGK Germany 

3

F 

10-21

TSCA 

Yes

HazardClass 

3

PackingGroup 

III

HS Code 

29319090

MSDS

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

DIMETHYLKETENE METHYL TRIMETHYLSILYL ACETAL Usage And Synthesis

Chemical Properties

Clear colorless liquid

Physical properties

bp 35 °C/15 mmHg; d 0.858 g cm?3.

Uses

1-Methoxy-2-methyl-1-(trimethylsilyloxy) propene is widely used as functional equivalent of enolate of methyl isobutyrate; ester enolate surrogate in electrophilic reactions including alkylation, aldol reaction, Michael reaction, initiator for group transfer polymerization of acrylates, nitroarylation, oxidation, dimerization, and cycloadditions.

Uses

1-Methoxy-2-methyl-1-(trimethylsiloxy)propene is used in the synthesis of chiral β-lactams by reacting with (S)-alkylidene(1-arylethyl)amines in the presence of titanium tetrachloride. It acts as a catalyst or initiator in the group-transfer polymerization. It is also used as a versatile reagent in conjugate addition4 and aldol reactions.

Preparation

The title compound is a prototypical ketene silyl acetal (KSA) that can been prepared by either of the two most commonly employed methods: (a) deprotonation of the |á-hydrogen of an ester followed by silylation (1),16 and (b) metal-catalyzed hydrosilylation of |á,|?-unsaturated esters(2).

Purification Methods

Add Et2O, wash with cold H2O, dry (Na2SO4), filter, evaporate Et2O, and distil the oily residue in a vacuum. [Ainsworth et al. J Organometal Chem 46 59 1972.]

DIMETHYLKETENE METHYL TRIMETHYLSILYL ACETAL(31469-15-5)Related Product Information

• 2-(4-BROMOPHENYL)-1,3-DIOXOLANE
• 1-(2-TRIMETHYLSILOXYETHOXY)-1-TRIMETHYLSILOXY-2-METHYLPROPENE
• 1-METHOXY-1-TRIMETHYLSILYLOXYPROPENE
• VINYLOXYTRIMETHYLSILANE
• DIMETHYLKETENE METHYL TRIMETHYLSILYL ACETAL
• 2-METHYL-1-(TRIMETHYLSILOXY)-1-PROPENE