7486-35-3

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VINYLTRI-n-BUTYLTIN

Product Code: SNV9100

Cas No: 7486-35-3

R&D quantities:

25 g
$402.00
5 g
$102.00
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.

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

    • Boiling Point: 104-6° / 3.5

    EINECS Number: 231-291-4

    Molecular Weight: 317.08

    Specific Gravity: 1.085

    Flashpoint: >110°C (>230°F)

    HMIS Key: 2-2-0-X

    Hydrolytic Sensitivity: 1: no significant reaction with aqueous systems

    Formula: C14H30Sn

    Refractive Index: 1.4776

    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.