1-BROMOVINYLTRIMETHYLSILANE

Product Code: SIB1910.0
CAS No: 13683-41-5
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13683-41-5
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5 g
$174.00

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

  • Einecs Number

    237-195-9
  • HMIS

    2-4-1-X
  • Molecular Formula

    C5H11BrSi
  • Molecular Weight (g/mol)

    179.13
  • TSCA

    No
  • Boiling Point (˚C/mmHg)

    55-57/80
  • Density (g/mL)

    1.163
  • Flash Point (˚C)

    15
  • Refractive Index @ 20˚C

    1.4580

Additional Properties

  • Hydrolytic Sensitivity

    4: no reaction with water under neutral conditions

    • Application

    Review of synthetic utility.1
    Starting material for preparation of ?-trimethylsilylvinylketone.2
    Starting material for preparation of trisubstituted olefins.3
    Potential for cross-coupling protocols to yield ?-substituted vinylsilanes.4
    Reacts with dichlorocarbene followed by fluoride-promoted elimination to formcyclopropenes.5

    Fieser

    F&F: Vol. 7, p 193; Vol. 8, p 56, p 515; Vol. 9, p 56; Vol. 10, p 442; Vol. 11, p 286.

    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. 109-110.
    2. Stork, G. et al. J. Am. Chem. Soc. 1973, 95, 6152.
    3. Miller, R. et al. J. Org. Chem. 1979, 44, 4623.
    4. Larson, G. L. “Silicon-Based Cross-Coupling Reagents” Gelest, Inc. 2011.
    5. Billups, W. E. et al. Tetrahedron Lett. 1984, 25, 3935.

    Safety

  • 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.

    1-Bromovinyltrimethylsilane; α-Bromovinyltrimethylsilane

  • Useful for cross-coupling to 1-substituted vinylsilanes
  • Employed in cyclopentene annulations
  • Starting material for preparation of ?-trimethylsilylvinylketone
  • Starting material for preparation of trisubstituted olefins
  • Potential for cross-coupling protocols to yield ?-substituted vinylsilanes
  • Reacts with dichlorocarbene followed by fluoride-promoted elimination to formcyclopropenes
  • 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