13683-41-5

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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