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688-73-3

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TRI-n-BUTYLTIN HYDRIDE

Product Code: SNT8130

Cas No: 688-73-3

R&D quantities:

1 kg
$1,463.00
50 g
$116.00
10 g
$30.00
Tin-Based Reducing Agent
Tri-n-butyltin hydride; Tributylstannane; Tributylhydridotin; Tributyltin

  • Storage Stability: 5 °C: ~6 months

  • Storage Stability: 25 °C: ~6 weeks

  • Viscosity, 20 °: 1.5 cSt
  • Decomposes >250 °C
  • Vapor pressure, 20 °C: 0.02 mm
  • Undergoes hydrostannation reactions
  • Reduces organic halides
  • Reduces acid chlorides to aldehydes
  • Reduces enol triflates to olefins
  • Effects partial reductions of chlorosilanes
  • Rate constant for aryl radical: 7.8 x108 M-1s-1
  • Reacts with HfCl4 to provide hafnium hydride species, which reduces aldehydes and ketones
  • Review published by Chuit, C. et al. Synthesis 1982, 981
  • Catalyzes the Si–H reduction of α,β-unsaturated ketones
  • Useful in the reductive amination of ketones and aldehydes to form 3° amines
  • Selective reducing agent

    • Boiling Point: 78-80° / 0.2

    EINECS Number: 211-704-4

    Molecular Weight: 291.05

    Alternative Name: TRIBUTYLSTANNANE

    Specific Gravity: 1.082

    Flashpoint: 40°C (104°F)

    HMIS Key: 3-2-1-X

    Hydrolytic Sensitivity: 7: reacts slowly with moisture/water

    Formula: C12H28Sn

    Refractive Index: 1.4731

    TSCA: TSCA

    Application: Reviewed.1
    Reduces organic halides.2
    Reduces acid chlorides to aldehydes.3
    Reduces enol triflates to olefins.4
    Effects partial reductions of chlorosilanes.5
    Rate constant for aryl radicals: 7.8 x108 M-1s-1 .6
    Reductions reviewed.7
    Reacts with HfCl4 to provide hafnium hydride species, which reduces aldehydes and ketones.8

    Reference: 1. RajanBabu, T. V. in Encyclopedia of Reagents for Organic Synthesis 1995, Volume 8, 5016-5023.
    2. Van Der Kerk, G. F&F: Vol. 1, p 1192; J. Appl. Chem. 1937, 7, 366.
    3. Kuivala, H. J. Org. Chem. 1961, 25, 284; J. Am. Chem. Soc. 1966, 88, 571.
    4. Scott, W. et al. J. Am. Chem. Soc. Soc. 1986, 108, 3033.
    5. Paetzold, U. et al. J. Organomet. Chem. 1996, 508, 147.
    6. Garden, S. et al. J. Org. Chem. 1996, 61, 805.
    7. Neumann, W. Synthesis 1987, 665.
    8. Shibata, I. et al. Synlett 2009, 1495.

    Fieser: F&F: Vol. 1, p. 1192; Vol. 2, p. 424; Vol. 3, p. 294; Vol. 4, p. 518; Vol. 5, p. 685; Vol. 6, p. 604; Vol. 7, p. 497, Vol. 9, p. 476; Vol. 10, p. 411; Vol. 11, p. 545; Vol. 12, p. 516; Vol 13, p 316; Vol. 14, p. 312; Vl. 15, p. 325; Vol. 16, p. 343; Vol. 19, pp. 352-359; Vol. 21, p. 333.

    Additional Properties: Decomposes >250°
    Stabilized with 50 ppm BHT
    Undergoes hydrostannation reactions; selective reducing agent
    Vapor pressure, 20°: 0.02 mm