Vinyltrimethylsilane

[754-05-2] C5H12Si (MW 100.26) InChI = 1S/C5H12Si/c1-5-6(2,3)4/h5H,1H2,2-4H3 InChIKey = GCSJLQSCSDMKTP-UHFFFAOYSA-N (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) Physical Data: bp 55–57 °C; 0.691 g cm−3; 1.391. Solubility: sol most common organic solvents (THF, Et2O, benzene, CH2Cl2, etc.) Form Supplied in: commercially available from several suppliers. Analysis of Reagent Purity: characterized by 1H, 13C, and 29Si NMR,2 and IR.3 1H NMR (500 MHz) (CDCl3): δ 0.08 (9H, s), 5.67 (1H, dd, Jtrans = 20.3 MHz, Jgem = 3.8 Hz), 5.93 (1H, dd, Jcis = 14.7 Hz, Jgem = 3.8 Hz), 6.17 (1H, dd, Jtrans = 20.3 Hz, Jcis = 14.7 Hz) ppm; 13C NMR (125 MHz) (CDCl3): δ −1.62, 130.88, 140.27 ppm; 29Si NMR (19.9 MHz) ((MeO)4Si): δ −71.70 ppm; IR (CCl4): ν 1594 cm−1. Preparative Method: prepared in 67–91% yield from Vinylmagnesium Bromide and Chlorotrimethylsilane in THF.4, 5 Purification: fractional distillation at 1 atm using an efficient Vigreux column. Some difficulty in removing trace amounts of THF (bp 67 °C) has been reported. Handling, Storage, and Precautions: highly flammable; flash point −34 °C; hygroscopic. The reagent should be used in a well ventilated hood. Contact with the eyes and skin should be avoided.