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754-05-2
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Product data and descriptions listed are typical values, not intended to be used as specification.

  • Einecs Number

    212-042-9
  • HMIS

    2-4-0-X
  • Molecular Formula

    C5H12Si
  • Molecular Weight (g/mol)

    100.24
  • TSCA

    Yes
  • Autoignition Temp (˚C)

    295
  • Boiling Point (˚C/mmHg)

    55
  • Density (g/mL)

    0.6903
  • Flash Point (˚C)

    -20 °C
  • Melting Point (˚C)

    -132°
  • Refractive Index @ 20˚C

    1.3910
  • Additional Viscosity (cSt)

    '0.5, 20
  • Viscosity at 25 ˚C (cSt)

    0.5

Additional Properties

  • Hydrolytic Sensitivity

    1: no significant reaction with aqueous systems
  • Application

    Review of synthetic utility.1
    Polymerization catalyzed by alkyllithium compounds.2,3,4
    Synthetic reactions of vinylsilanes reviewed.5,6
    Undergoes Heck coupling to (E)-?-substituted vinyltrimethylsilanes, which can be cross-coupled further.7
    Reacts w/ azides to form trimethylsilyl-substituted aziridines.8

    Fieser

    F&F: Vol. 9, p 498; Vol. 10, p 44; Vol. 11, p 41; Vol. 12, p 566.

    Reference

    1. Handbook of Reagents for Organic Synthesis, Reagents for Silicon-Mediated Organic Synthesis, Fuchs, P. L. Ed., John Wiley and Sons, Ltd., 2011, p. 755-761.
    2. Oku, J. et al. Polymer J. 1991, 23, 1377; Macromolecules 1992, 25, 2780.
    3. Gan, Y. et al. Macromolecules 1996, 29, 8285.
    4. Rickle, G. J. Macromol. Sci. 1987, A24, 93.
    5. Hudrlik, P. In New Applications of Organometallic Reagents in Organic Synthesis; Seyferth, D., Ed.; Elsevier: 1976.
    6. F&F: Vol. 5, p 375; Vol. 6, p 637.
    7. Jeffery, T. Tetrahedron Lett. 1999, 40, 1673.
    8. Bassindale, A. R. et al. J. Chem. Soc., Perkin Trans. 1 2000, 1173.

    Safety

  • Hazard Info

    oral rat, LD50: >2,000 mg/kg
  • Packaging Under

    Nitrogen
  • Alkenylsilane Cross-Coupling Agent

    The cross-coupling reaction is a highly useful methodology for the formation of carbon-carbon bonds. It involves two reagents, with one typically being a suitable organometallic reagent - the nucleophile - and the other a suitable organic substrate, normally an unsaturated halide, tosylate or similar - the electrophile.

    Vinyltrimethylsilane; Ethenyltrimethylsilane; Trimethylsilylethene; Trimethylvinylsilane

  • Viscosity, 20 °C: 0.5 cSt
  • ΔHcomb: 4,133 kJ/mol
  • ΔHfus: 7.7 kJ/mol
  • Copolymerization parameters- e,Q: 0.04, 0.029
  • Forms polymers which can be fabricated into oxygen enrichment membranes
  • Polymerization catalyzed by alkyllithium compounds
  • Reacts w/ azides to form trimethylsilyl-substituted aziridines
  • Undergoes Heck coupling to (E)-β-substituted vinyltrimethylsilanes, which can then be cross-coupled further
  • Extensive review of silicon based cross-coupling agents: Denmark, S. E. et al. "Organic Reactions, Volume 75" Denmark, S. E. ed., John Wiley and Sons, 233, 2011
  • Silicon Chemistry, Articles

    Silicon-Based Formation of Carbon-Carbon Bonds – Larson

    Hatanaka and Hiyama first reported the palladium-catalyzed, fluoride-promoted reaction of aryl, alkenyl, allyl, and ethynyltrimethylsilanes with aryl, vinil and allyl halides to form the respective cross-coupled products