Vinyltrimethylsilane CAS:754-05-2

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Vinyltrimethylsilane Basic information Product Name: Vinyltrimethylsilane Synonyms: CH2=CHSi(CH3)3;ethenyltrimethyl-silan;Silane, trimethylvinyl-;silane,trimethylvinyl-;Vinyltrimethysilane;VINYLTRIMETHYLSILANE;(TRIMETHYLSILYL)ETHYLENE;Vinyltrimethylsilane, VTMS CAS: 754-05-2 MF: C5H12Si MW: 100.23 EINECS: 212-042-9 Product Categories: Amides;Amines;and Other Vinyl Monomers;Chemical Synthesis;Materials Science;Monomers;Organometallic Reagents;Organosilicon;Others;Polymer Science;Vinyl Halides;Si (Classes of Silicon Compounds);Si-(C)4 Compounds;Vinylsilanes, Allylsilanes Mol File: 754-05-2.mol 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 color  Colorless to Almost colorless Specific Gravity 0.6903 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 Information 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 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.]



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