TRI-n-BUTYLSTANNYLTRIMETHYLSILANE

Product Code: SNT8585
CAS No: 17955-46-3
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17955-46-3
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2.5 g
$99.00
10 g
$317.00

Prices listed are EXW price (Morrisville, PA US) in USD. Prices vary depending on currency and Incoterms.

Product data and descriptions listed are typical values, not intended to be used as specification.

  • Synonyms

    TRIMETHYLSILYLTRI-n-BUTYLTIN
  • HMIS

    2-1-1-X
  • Molecular Formula

    C15H36SiSn
  • Molecular Weight (g/mol)

    363.22
  • TSCA

    No
  • Boiling Point (˚C/mmHg)

    102-103/0.5
  • Density (g/mL)

    1.040
  • Refractive Index @ 20˚C

    1.4880

Additional Properties

  • Hydrolytic Sensitivity

    1: no significant reaction with aqueous systems

    • Application

    Review of synthetic utility.1
    Undergoes cis addition to terminal acetylenes with Bu3Sn internal.2
    Intermediate for 3-substituted cyclobutenone.3
    Sn-Si bond shown to react with COD Pt(cod)2 and phosphines to form bis((phosphino)silyl)tinplatinum(ll) complexes, which insert into acetylenes.4
    Used in the synthesis of ?-amidotributylstannanes.5

    Reference

    1. Handbook of Reagents for Organic Synthesis, Reagents for Silicon-Mediated Organic Synthesis, Fuchs, P. L. Ed., John Wiley and Sons, Ltd., 2011, p. 719-723.
    2. Chenard, B. et al. J. Org. Chem. 1986, 51, 3561.
    3. Liebeskind, L. S. et al. J. Org. Chem. 1994, 59, 7917.
    4. Sagawa, T. et al. Organometallics 2003, 22, 4433.
    5. Mita, T.; et al. Synthesis 2012, 194.

    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.

    Tri-n-butylstannyltrimethylsilane; Trimethylsilyltri-n-butyltin; Trimethyl(tributylstannyl)silane

  • Undergoes addition to olefins
  • Undergoes cis addition to terminal acetylenes with Bu3Sn internal
  • Intermediate for 3-substituted cyclobutenone
  • Sn–Si bond shown to react with COD Pt(cod)2 and phosphines to form bis((phosphino)silyl)tinplatinum(ll) complexes, which insert into acetylenes
  • Used in the synthesis of α-amidotributylstannanes
  • 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