17955-46-3

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TRI-n-BUTYLSTANNYLTRIMETHYLSILANE

Product Code: SNT8585

Cas No: 17955-46-3

R&D quantities:

10 g
$264.00
2.5 g
$82.00
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.

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

    • Boiling Point: 102-3° / 0.5

    Molecular Weight: 363.22

    Alternative Name: TRIMETHYLSILYLTRI-n-BUTYLTIN

    Specific Gravity: 1.040

    HMIS Key: 2-1-1-X

    Hydrolytic Sensitivity: 1: no significant reaction with aqueous systems

    Formula: C15H36SiSn

    Refractive Index: 1.4880

    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.