CYCLOTRIMETHYLENEDICHLOROSILANE

Product Code: SIC2568.0
CAS No: 2351-33-9
SDS Sheets: EU | US
Pack Size
Quantity
Price
 
10 g
$108.00
50 g
$429.00

Product data and descriptions listed are typical values, not intended to be used as specification.

  • Einecs Number

    219-084-7
  • Synonyms

    1,1-DICHLOROSILACYCLOBUTANE
  • HMIS

    3-4-1-X
  • Molecular Formula

    C3H6Cl2Si
  • Molecular Weight (g/mol)

    141.07
  • TSCA

    Yes
  • Boiling Point (˚C/mmHg)

    113-114
  • Density (g/mL)

    1.201
  • Flash Point (˚C)

    9
  • Refractive Index @ 20˚C

    1.4620

Additional Properties

  • Hydrolytic Sensitivity

    8: reacts rapidly with moisture, water, protic solvents
  • 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.

    Safety

  • Packaging Under

    Nitrogen
  • 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
  • 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