COMMERCIAL
97674-02-7

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1-ETHOXYVINYLTRI-n-BUTYLTIN

Product Code: SNE4620

Cas No: 97674-02-7

R&D quantities:

25 g
$528.00
5 g
$132.00
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.

1-Ethoxyvinyltri-n-butyltin; Tri-n-butyl(1-ethoxyvinyl)stannane
  • Transfer of acyl group equivalent in Stille Coupling
  • Can be cross-coupled with aryl chlorides
  • Used to acylate aryl triflates
  • Undergoes Stille cross-coupling reactions as employed in the syntheses of three cladiellins
  • Cross-couples with vinyl sulfides
  • Can be cross-coupled with heteroaromatic chlorides
  • 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

    • Boiling Point: 85-6° / 1

    Molecular Weight: 361.14

    Specific Gravity: 1.069

    Flashpoint: 113°C (235°F)

    HMIS Key: 3-2-1-X

    Formula: C16H34OSn

    Refractive Index: 1.4760

    Application: Can be cross-coupled with aryl chlorides.1
    Used to acylate aryl triflates.2
    Undergoes Stille cross-coupling reactions as employed in the syntheses of three cladiellins.3
    Cross-couples with vinyl sulfides.4
    Can be cross-coupled with heteroaromatic chlorides.5

    Reference: 1. Soderquist, J. et al. Tetrahedron Lett. 1983, 24, 2361.
    2. Stoltz, B. M. et al. J. Am. Chem. Soc. 2000, 122, 9044.
    3. Clark, J. S. et al. Angew. Chem., Int. Ed. Engl. 2010, 49, 9867.
    4. Schleiss, J.; Rollin, P.; Tatibouet, P. Angew. Chem., Int. Ed. Engl. 2010, 49, 577.
    5. Hong. L. et al. Bioorg. Med. Chem. Lett. 2010, 20, 679.