2-BROMOVINYLTRIMETHYLSILANE

Product Code: SIB1910.1
CAS No: 41309-43-7
SDS Sheets: EU | US
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41309-43-7
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Price
 
5 g
$219.00

Prices listed are EXW price (Morrisville, PA US) in USD. Prices vary depending on currency and Incoterms.

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
  • Purity (%)

    97%
  • TSCA

    No
  • Boiling Point (˚C/mmHg)

    50-51/52
  • Density (g/mL)

    1.167
  • Flash Point (˚C)

    29 °C
  • 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