VINYLTRI-n-BUTYLTIN

Product Code: SNV9100
CAS No: 7486-35-3
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5 g
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25 g
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2 kg
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Product data and descriptions listed are typical values, not intended to be used as specification.

  • Einecs Number

    231-291-4
  • HMIS

    2-2-0-X
  • Molecular Formula

    C14H30Sn
  • Molecular Weight (g/mol)

    317.08
  • TSCA

    No
  • Boiling Point (˚C/mmHg)

    104-106/3.5
  • Density (g/mL)

    1.085
  • Flash Point (˚C)

    >110 °C
  • Refractive Index @ 20˚C

    1.4776

Additional Properties

  • Hydrolytic Sensitivity

    1: no significant reaction with aqueous systems

    • Application

    Reviewed.1
    Intermediate for vinyllithium by exchange with phenyllithium.2
    With CO forms divinyl ketones on reaction with vinyl iodides.3
    Reacts with IC6H4CHO in DMF with PdCl2(CH3CN)2 to yield CH2=CHC6H4CHO.4
    Reacts with halopyrimidines to yield vinylpyrimidines.5
    Employed in one-pot synthesis of pyrroles.6

    Reference

    1. Scott, W. J.; Moretto, A. F. in Encyclopedia of Reagents for Organic Synthesis 1995, Volume 8, 5503-5506.
    2. Seyferth, D. et al. J. Am. Chem. Soc. 1961, 83, 3583.
    3. Goure, W. et al. F&F: Vol. 12, p 45; J. Am. Chem. Soc. 1984, 106, 6417.
    4. Bumagin, N. Chem. Abstr. 111, 214179; Metal Org. Chem. 1989, 2, 475.
    5. Kondo, Y. et al. Chem. Pharm. Bull. 1989, 37, 2814.
    6. Nakamura, M. et al. Org. Lett. 1999, 1, 1505.

    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.

    Vinyltri-n-butyltin; Tributylethenylstannane; Tributylvinylstannane

  • Copolymerization parameters - e,Q: 0.800, 0.024
  • Stille Coupling vinylation reagent
  • Intermediate for vinyllithium by exchange with phenyllithium
  • With CO forms divinyl ketones on reaction with vinyl iodides
  • Reacts with IC6H4CHO in DMF with PdCl2(CH3CN)2 to yield CH2=CHC6H4CHO
  • Reacts with halopyrimidines to yield vinylpyrimidines
  • Employed in one-pot synthesis of pyrroles
  • 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