(E)-HEPTENYLDIISOPROPYLSILANOL

Product Code: SIH5844.5
CAS No: 261717-41-3
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261717-41-3
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2.5 g
$455.00

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

  • HMIS

    2-2-0-X
  • Molecular Formula

    C13H28OSi
  • Molecular Weight (g/mol)

    228.45
  • Purity (%)

    97%
  • TSCA

    No
  • Boiling Point (˚C/mmHg)

    88° / 0.1
  • Density (g/mL)

    0.877
  • Refractive Index @ 20˚C

    1.4640

Additional Properties

  • Hydrolytic Sensitivity

    4: no reaction with water under neutral conditions

    • Application

    Undergoes Pd-catalyzed cross-coupling with activated aromatic iodides.1
    Stable silanol for cross-coupling vinylations.2,3,4
    Vinyl silanols cross-couple w/ aryl triflates and nonaflates.5
    Potassium salts of silanols cross-couple in absence of fluoride.6

    Reference

    1. Denmark, S. et al. Org. Syn. 2005, 81, 42.
    2. Denmark, S. E.; Sweis, R. F. J. Am. Chem. Soc. 2001, 123, 6439.
    3. Denmark, S. E.; Pan, W. J. Organomet. Chem. 2002, 653, 98.
    4. Denmark, S. E.; Wehrli, D. Org. Lett. 2000, 2, 565.
    5. Denmark, S. E.; Sweis, R. F. Org. Lett. 2002, 4, 3771.
    6. Denmark, S. E.; Kallemeyn, J. M. J. Am. Chem. Soc. 2006, 128, 15958.

    Safety

  • Packaging Under

    Nitrogen

    • 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.

    (E)-Heptenyldiisopropylsilanol; Hydroxydiisopropylheptenylsilane

  • Stable silanol for cross-coupling of olefinic group
  • Vinylsilanols couple w/ aryl triflates and nonflates
  • Undergoes Pd-catalyzed cross-coupling with activated aromatic iodides
  • Used for cross-coupling vinylations
  • Vinyl silanols cross-couple w/ aryl triflates and nonaflates
  • Potassium salts of silanols cross-couple in absence of fluoride
  • 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