TETRAVINYLTIN

Product Code: SNT7906
CAS No: 1112-56-7
SDS Sheets: EU | US
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1112-56-7
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Quantity
Price
 
5 g
$100.00
25 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.

  • Einecs Number

    214-193-6
  • HMIS

    3-3-0-X
  • Molecular Formula

    C8H12Sn
  • Molecular Weight (g/mol)

    226.88
  • TSCA

    No
  • Boiling Point (˚C/mmHg)

    160-163
  • Density (g/mL)

    1.257
  • Flash Point (˚C)

    40 °C
  • Refractive Index @ 20˚C

    1.4914

Additional Properties

  • Hydrolytic Sensitivity

    1: no significant reaction with aqueous systems

    • Application

    Reviewed.1
    Asymmetrically allylates prochiral ketones with high ee's.2
    Allylates ?-keto esters with high enantioselectivty.3

    Reference

    1. Scott, W. J.; Moretto, A. F. in Encyclopedia of Reagents for Organic Synthesis 1995, Volume 7, 4830-4831.
    2. Wooten, A. J. et al. Org. Lett. 2007, 9, 381.
    3. Zheng, K. et al. J. Org. Chem. 2007, 72, 8478.

    Safety

  • Packaging Under

    Nitrogen

    • Organotin 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.

    Tetravinyltin; Tetraethenylstannane

  • Stille Coupling vinylation reagent
  • Source for vinyl lithium
  • Polymerization catalyst
  • Asymmetrically allylates prochiral ketones with high ee’s
  • Allylates α-keto esters with high enantioselectivty
  • 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

    • Metal-Organic Chemistry, Articles

    Introduction to Organotin Chemistry – Bossert

    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