CYCLOTRIMETHYLENEDICHLOROSILANE

Product Code: SIC2568.0
CAS No: 2351-33-9
SDS Sheets: EU | US
Pack Size
Quantity
Price
 
10 g
$650.00
50 g
$2,575.00

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.

  • Einecs Number

    219-084-7
  • Synonyms

    1,1-DICHLOROSILACYCLOBUTANE
  • HMIS

    3-4-1-X
  • Molecular Formula

    C3H6Cl2Si
  • Molecular Weight (g/mol)

    141.07
  • Purity (%)

    97%
  • TSCA

    Yes
  • Boiling Point (˚C/mmHg)

    113-114
  • Density (g/mL)

    1.201
  • Flash Point (˚C)

    9 °C
  • 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