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HomeProduct name listVinyltrimethylsilane

Vinyltrimethylsilane

Synonym(s):(Trimethylsilyl)ethylene;Ethenyltrimethylsilane;Trimethyl(vinyl)silane

  • CAS NO.:754-05-2
  • Empirical Formula: C5H12Si
  • Molecular Weight: 100.23
  • MDL number: MFCD00008606
  • EINECS: 212-042-9
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-08-21 22:41:43
Vinyltrimethylsilane Structural

What is Vinyltrimethylsilane?

Chemical properties

clear colourless liquid

Physical properties

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

The Uses of Vinyltrimethylsilane

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.

The Uses of Vinyltrimethylsilane

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

The Uses of Vinyltrimethylsilane

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.

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.]

Properties of Vinyltrimethylsilane

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
color  Colorless to Almost colorless
Specific Gravity 0.6903
Hydrolytic Sensitivity 1: no significant reaction with aqueous systems
BRN  956572
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 information for Vinyltrimethylsilane

Signal word Danger
Pictogram(s)
ghs
Flame
Flammables
GHS02
ghs
Exclamation Mark
Irritant
GHS07
ghs
Health Hazard
GHS08
GHS Hazard Statements H225:Flammable liquids
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H351:Carcinogenicity
Precautionary Statement Codes P202:Do not handle until all safety precautions have been read and understood.
P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P233:Keep container tightly closed.
P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P308+P313:IF exposed or concerned: Get medical advice/attention.

Computed Descriptors for Vinyltrimethylsilane

InChIKey GCSJLQSCSDMKTP-UHFFFAOYSA-N

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