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754-05-2

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VINYLTRIMETHYLSILANE

Product Code: SIV9250.0

Cas No: 754-05-2

R&D quantities:

100 g
$237.00
10 g
$33.00
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
  • Boiling Point: 55°

    EINECS Number: 212-042-9

    Melting Point: -132°

    Molecular Weight: 100.24

    Specific Gravity: 0.6903

    Flashpoint: -20°C (-4°F)

    HMIS Key: 2-4-0-X

    Hydrolytic Sensitivity: 1: no significant reaction with aqueous systems

    Formula: C5H12Si

    Refractive Index: 1.3910

    TSCA: TSCA

    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

    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.

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

    Additional Properties: 295
    ?Hcomb: 987.3 kcal/mole
    ?Hfus: 7.7 kJ/mole
    Forms polymers which can be fabricated into oxygen enrichment membranes