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
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 | n |
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) |
Flame Flammables GHS02 Exclamation Mark Irritant GHS07 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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