Vinyltrimethylsilane Property

Melting point:

-132°C

Boiling point:

55 °C (lit.)

Density 

0.684 g/mL at 25 °C (lit.)

vapor pressure 

4.44 psi ( 20 °C)

refractive index 

n20/D 1.391(lit.)

Flash point:

<-30 °C

storage temp. 

Inert atmosphere,2-8°C

solubility 

Miscible with tetrahydrofuran, diethyl ether, benzene and dichloromethane.

form 

liquid

Specific Gravity

0.6903

color 

Colorless to Almost colorless

Hydrolytic Sensitivity

1: no significant reaction with aqueous systems

BRN 

956572

InChIKey

GCSJLQSCSDMKTP-UHFFFAOYSA-N

CAS DataBase Reference

754-05-2(CAS DataBase Reference)

NIST Chemistry Reference

Silane, ethenyltrimethyl-(754-05-2)

EPA Substance Registry System

Silane, ethenyltrimethyl- (754-05-2)

Safety

Hazard Codes 

F,Xn

Risk Statements 

11-22-36/37/38-40

Safety Statements 

16-26-33-36-36/37/39-36/37

RIDADR 

UN 1993 3/PG 1

WGK Germany 

1

TSCA 

Yes

HazardClass 

3

PackingGroup 

II

HS Code 

29319090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H225Highly Flammable liquid and vapour

H315Causes skin irritation

H319Causes serious eye irritation

H351Suspected of causing cancer

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

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

P233Keep container tightly closed.

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.

P308+P313IF exposed or concerned: Get medical advice/attention.

Vinyltrimethylsilane Chemical Properties,Usage,Production

Chemical Properties

clear colourless liquid

Physical properties

bp 55–57 °C; d20 4 0.691 g cm?3; n20 D 1.391.

Uses

Preparation of silyl-ethers by Rh(I) catalysis.1

Uses

Vinyltrimethylsilane is used in semiconductor processing. It is involved in the Preparation of silyl-ethers by Rh(I) catalysis. Further, it is used in the preparation of trimethylsilylethyl sulfoxides which in the presence of fluoride ion generate sulfenate nucleophiles.

Uses

Vinyltrimethylsilane is ethylene equivalent in electrophilic substitution reactions; precursor to 3-trimethylsilyl-3-buten-2-one, a methyl vinyl ketone surrogate for Robinson annulations; homologation of aldehydes to α,β-unsaturated aldehydes. It takes part in the reactions of Synthesis of Vinyl Aryl Sulfides, Synthesis of 3-Triethylsilyl-3-buten-2-one, Synthesis of α,β-Unsaturated Primary Amides, Synthesis of α,β-Unsaturated Aldehydes, Synthesis of Bicyclopentenones, Synthesis of 1-Chlorocyclopropene, Radical Addition Reactions of Vinyltrimethylsilane, Reaction of Vinyltrimethylsilane with 2-Azaallylanions, Regioselective Hydroesterification of Vinyltrimethylsilane, 3 + 2 Cycloaddition of Vinyltrimethylsilane with Nitrones, Addition of α-Iodo-α,α-Difluoroketones to Vinyltrimethylsilane, Addition of α-Iodosulfones to Vinyltrimethylsilane, Titanium-mediated Formation of Trimethylsilylcyclopropanols, β-Trimethylsilyl Ketones and Cyclopropenes, Hydrogen Acceptor Catalyst in the Conversion of Alcohols to Hydrogenated Wittig Adducts, Formation of 2-Trimethylsilylaziridines, Formation of Sulfonyl Chlorides, Improved Synthesis of 2-Trimethylsilylethylsulfonyl Chloride, Formation of an Iron Carbonyl Trienone Complex, Synthesis of 2-Phenyl-2-Trimethylsilylethanol, Synthesis of 2-Vinylanilines, Decarbonylative Vinylation of an Aromatic Ester, Asymmetric Epoxidation of Vinyltrimethylsilane, Direct Silylation of Heteroarylcarbonyl Compounds, Trimethylsilylation of Vinylboronates, etc.

Preparation

Prepared in 67–91% yield from vinylmagnesium bromide and chlorotrimethylsilane in THF.

Flammability and Explosibility

Flammable

Purification Methods

If the 1H NMR spectrum shows impurities, then dissolve it in Et2O, wash it with aqueous NH4Cl solution, dry over CaCl2, filter, evaporate and distil it at atmospheric pressure in an inert atmosphere. It is used as a co-polymer and may polymerise in the presence of free radicals. It is soluble in CH2Cl2. [Nagel & Post J Org Chem 17 1379 1952, Beilstein 4 IV 3922.]