Additional Properties
- Einecs Number 211-704-4
- Synonyms TRIBUTYLSTANNANE
- HMIS 3-2-1-X
- Molecular Formula C12H28Sn
- Molecular Weight (g/mol) 291.05
- TSCA Yes
- Boiling Point (˚C/mmHg) 78-80/0.2
- Density (g/mL) 1.082
- Flash Point (˚C) 40 °C
- Refractive Index @ 20˚C 1.4731
- Additional Viscosity (cSt) '1.5, 20
- Viscosity at 25 ˚C (cSt) '1.5
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
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.
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.
Safety
Tin-Based Reducing Agent
Tri-n-butyltin hydride; Tributylstannane; Tributylhydridotin; Tributyltin
Storage Stability: 5 °C: ~6 months
Storage Stability: 25 °C: ~6 weeks
Metal-Organic Chemistry, Articles