Pack Size
Quantity
Price
 
5 g
$121.00

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

  • Synonyms

    2-(TRIMETHYLSILYL)VINYLBROMIDE
  • HMIS

    2-3-1-X
  • Molecular Formula

    C5H11BrSi
  • Molecular Weight (g/mol)

    179.13
  • Boiling Point (˚C/mmHg)

    50-1° / 52
  • Density (g/mL)

    1.167
  • Flash Point (˚C)

    29°C (84°F)
  • Refractive Index @ 20˚C

    1.467

Additional Properties

  • Hydrolytic Sensitivity

    3: reacts with aqueous base
  • Application

    Potential for cross-coupling protocols to yield ?-substituted vinylsilanes.1
    Starting point for substituted vinyl silanes

    Reference

    1. Larson, G. L. “Silicon-Based Cross-Coupling Reagents” Gelest, Inc. 2011.
    F&F: Vol. 11, p 82.

    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.

    2-Bromovinyltrimethylsilane; 2-(Trimethylsilyl)vinylbromide

  • Contains 10-15% cis-isomer
  • Slowly decomposes above 60 °C yielding ethylene
  • Useful for cross-coupling to 2-substituted vinylsilanes
  • Potential for cross-coupling protocols to yield β-substituted vinylsilanes
  • 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