13683-41-5

All structures are computer generated. Please rely on the product data below for placing your order. If you see any errors in structures, please email customer service so that they can be addressed.

1-BROMOVINYLTRIMETHYLSILANE

Product Code: SIB1910.0

Cas No: 13683-41-5

R&D quantities:

5 g
$174.00
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.

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

    • Boiling Point: 55-7° / 80

    EINECS Number: 237-195-9

    Molecular Weight: 179.13

    Specific Gravity: 1.163

    Flashpoint: 15°C (59°F)

    HMIS Key: 2-4-1-X

    Hydrolytic Sensitivity: 4: no reaction with water under neutral conditions

    Formula: C5H11BrSi

    Refractive Index: 1.4580

    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

    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.

    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.

    Additional Properties: Employed in cyclopentene annulations