41309-43-7

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2-BROMOVINYLTRIMETHYLSILANE

Product Code: SIB1910.1

Cas No: 41309-43-7

R&D quantities:

5 g
$121.00

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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
  • Boiling Point: 50-1° / 52

    Molecular Weight: 179.13

    Alternative Name: 2-(TRIMETHYLSILYL)VINYLBROMIDE

    Specific Gravity: 1.167

    Flashpoint: 29°C (84°F)

    HMIS Key: 2-3-1-X

    Hydrolytic Sensitivity: 3: reacts with aqueous base

    Formula: C5H11BrSi

    Refractive Index: 1.467

    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.

    Additional Properties: Contains 10-15% cis-isomer
    Slowly decomposes above 60° yielding ethylene