TRI-n-BUTYLSTANNYLTRIMETHYLSILANE

Product Code: SNT8585
CAS No: 17955-46-3
SDS Sheets: EU | US
Navigate this page...
17955-46-3
Save for Later
Pack Size
Quantity
Price
 
2.5 g
$82.00
10 g
$264.00

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)

    102-3° / 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