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| Vinyltrimethylsilane Basic information |
| Vinyltrimethylsilane Chemical Properties |
| 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.) | | Fp | <-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) |
| Vinyltrimethylsilane Usage And Synthesis |
| 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.] |
| Vinyltrimethylsilane Preparation Products And Raw materials |
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