POTASSIUM TRIETHYLSILANOLATE, 95%

Product Code: SIP6899.0
CAS No: 25706-33-6
SDS Sheets: EU | US
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25706-33-6
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Quantity
Price
 
10 g
$100.00
50 g
$396.00

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.

  • HMIS

    3-2-1-X
  • Molecular Formula

    C6H15KOSi
  • Molecular Weight (g/mol)

    170.37
  • Purity (%)

    95%
  • TSCA

    No
  • Boiling Point (˚C/mmHg)

    NA

Additional Properties

  • Hydrolytic Sensitivity

    7: reacts slowly with moisture/water

    • Application

    Used as a nucleophiles in the enantioselective formation of allyl alcohols from allyl carbonates.1
    Employed in an inexpensive vinylation of aryl bromides.2
    Catalyst for the cross-coupling of aryl and vinylsilanes.3

    Reference

    1. Lyothier, I. et al. Angew. Chem., Int. Ed. Engl. 2006, 45, 6204.
    2. Denmark, S. E.; Butler, C.R. J. Am. Chem. Soc. 2008, 130, 3690.
    3. Jeffery, T. Tetrahedron Lett. 1999, 40, 1673.

    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.

    Potassium triethylsilanolate; Potassium triethylsiloxide; Triethylsilanol, potassium salt

  • Soluble: methylene chloride, THF
  • Catalyst for the cross-coupling of aryl and vinylsilanes
  • Greater solubility and reactivity than KOSiMe3
  • Used as a nucleophiles in the enantioselective formation of allyl alcohols from allyl carbonates
  • Employed in an inexpensive vinylation of aryl bromides
  • 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