1-ETHOXYVINYLTRI-n-BUTYLTIN

Product Code: SNE4620
CAS No: 97674-02-7
SDS Sheets: EU | US
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97674-02-7
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5 g
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25 g
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2 kg
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20 kg
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Product data and descriptions listed are typical values, not intended to be used as specification.

  • HMIS

    3-2-1-X
  • Molecular Formula

    C16H34OSn
  • Molecular Weight (g/mol)

    361.14
  • TSCA

    No
  • Boiling Point (˚C/mmHg)

    85-86/1
  • Density (g/mL)

    1.069
  • Flash Point (˚C)

    113 °C
  • Refractive Index @ 20˚C

    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.

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.

    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

    • 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