2351-33-9

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CYCLOTRIMETHYLENEDICHLOROSILANE

Product Code: SIC2568.0

Cas No: 2351-33-9

R&D quantities:

50 g
$429.00
10 g
$108.00
Silane 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.

Cyclotrimethylenedichlorosilane; 1,1-Dichlorosilacyclobutane
  • Reaction with LiN(iPr)2 and CH2X2 provides 1,1-dimethyl-2-halosilacyclopentanes
  • Arylchlorosilyl derivatives used in cross-coupling to biaryls
  • Vinylchlorosilyl derivatives used in cross-coupling to 1,3-butadienes
  • Starting material for spirocyclic organosilanes
  • Precursor for aryl-substituted silacyclobutanes useful for aryl cross-coupling reactions
  • 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: 113-4°

    EINECS Number: 219-084-7

    Molecular Weight: 141.07

    Alternative Name: 1,1-DICHLOROSILACYCLOBUTANE

    Specific Gravity: 1.201

    Flashpoint: 9°C (48°F)

    HMIS Key: 3-4-1-X

    Hydrolytic Sensitivity: 8: reacts rapidly with moisture, water, protic solvents

    Formula: C3H6Cl2Si

    Refractive Index: 1.4620

    TSCA: TSCA

    Application: Reaction with LiN(iPr)2 and CH2X2 provides 1,1-dimethyl-2-halosilacyclopentanes.1
    Arylchlorosilyl derivatives used in cross-coupling to biaryls.2
    Vinylchlorosilyl derivatives used in cross-coupling to 1,3-butadienes.3
    Starting material for spirocyclic organosilanes.4

    Reference: 1. Matsumoto, K. Tetrahedron 1993, 49, 8487.
    2. Denmark, S. E.; Wu, Z. Org. Lett. 1999, 1, 1495.
    3. Denmark, S. E.; Choi, J. Y. J. Am. Chem. Soc. 1999, 121, 5821.
    4. Déjean, V. et al. Organometallics 2000, 19, 711.

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