ALLYLTRI-n-BUTYLTIN

Product Code: SNA0500
CAS No: 24850-33-7
SDS Sheets: EU | US
COMMERCIAL
24850-33-7
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Quantity
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10 g
$59.00
50 g
$231.00
2 kg
$3,662.00
18 kg
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Product data and descriptions listed are typical values, not intended to be used as specification.

  • Einecs Number

    246-494-3
  • HMIS

    2-2-1-X
  • Molecular Formula

    C15H32Sn
  • Molecular Weight (g/mol)

    331.11
  • Boiling Point (˚C/mmHg)

    88-92° / 0.2
  • Density (g/mL)

    1.068
  • Flash Point (˚C)

    103°C (217°F)
  • Refractive Index @ 20˚C

    1.4846

Additional Properties

  • Hydrolytic Sensitivity

    1: no significant reaction with aqueous systems
  • Application

    Reviewed.1
    Conjugatively allylates alkylidene Meldrum’s acids.10
    Generates homoallylic amines with aldehydes and amines.11
    Allylates bromides and chloroethers.,2,3
    Radical initiation induces 1,2-addition of allyltins and alkyl iodides to electron deficient alkenes.4
    Polymerization by Natta catalyst - Et3Al-TiCl4.5
    Converts aldehydes to homoallylic alcohols and imines to homoallylic amines.6
    Converts combination of aldehyde and amine to homoallylic amines.7
    Enantioselectively generates homoallylic amines in a 3-component reaction scheme.8
    Adds enantioselectively to prochiral ketones to form homoallyl alcohols in good enantioselectively.9

    Fieser

    F&F: Vol. 9, p 8; Vol. 11, p 15; Vol. 12, p 21; Vol. 13, p. 10; Vol. 14, p. 14; Vol. 16, p. 7; Vol. 17, p 12.

    Reference

    1. Castellino, S. in Encyclopedia of Reagents for Organic Synthesis 1995, Volume 1, 125-128.
    10. Duma, A. N.; Fillion, E. Org. Lett. 2009, 11, 1919.
    11. Narsaiah, A. et al. Synthesis, 2010, 1609.
    2. Corey, E. et al. Tetrahedron Lett. 1990, 31, 3715.
    3. Keck, G. et al. J. Am. Chem. Soc. 1982, 104, 5829.
    4. Mizuno, K. et al. F&F: Vol. 14, p 16; J. Am. Chem. Soc. 1988, 110, 1288.
    5. Montecatini. Soc. Chem. Abstr. 53, 1837; Ital. Patent 589,299, 1959.
    6. Shen, W. et al. Tetrahedron Lett. 2008, 49, 4047.
    7. Kalita, P. K.; Phukan, P. Tetrahedron Lett. 2008, 49, 5495.
    8. Li, X. et al. Chem. Eur. J. 2008 14, 4796.
    9. Lu, J. et al. Tetrahedron Lett. 2005, 46, 7435.

    Safety

  • Packaging Under

    Nitrogen