Tributyltin hydride
| Tributyltin hydride | |
|---|---|
 |
 |
 |
|
|
Tributylstannane[1] |
|
| Identifiers | |
| CAS number | 688-73-3  |
| PubChem | 5948 |
| ChemSpider | 5734  |
| EC number | 211-704-4 |
| MeSH | Tributyltin |
| ChEBI | CHEBI:27086 |
| Beilstein Reference | 3587329 |
| Gmelin Reference | 4258 |
| Jmol-3D images | Image 1 |
|
|
|
|
| Properties | |
| Molecular formula | SnC12H28 |
| Molar mass | 291.06 g mol-1 |
| Exact mass | 292.121297467 g mol-1 |
| Density | 1.082 g cm-3 |
| Boiling point |
80 °C, 353 K, 176 °F (at 50 Pa) |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
|
| Infobox references | |
Tributyltin hydride is an organotin compound with the formula (C4H9)3SnH. It is a colorless liquid that is soluble in organic solvents. The compound is used as a source of hydrogen atoms in organic synthesis.
Contents |
[edit] Synthesis and characterization
The compound is produced by reduction of tributyltin oxide with polymethylhydrosiloxane (Bu = CH3CH2CH2CH2):[2]
- (Bu3Sn)2O + 2/n (MeSi(H)O)n → 2 Bu3SnH + 1/n [(MeSiO)2O]n
The hydride is a distillable liquid that is mildly sensitive to air, decomposing to (Bu3Sn)2O. Its IR spectrum exhibits a strong band at 1814 cm-1 for νSn-H.
[edit] Applications
It is a useful reagent in organic synthesis. Combined with azobisisobutyronitrile or by irradiation with light, tributyltin hydride converts organic halides (and related groups) to the corresponding hydrocarbon. This process occurs via a radical chain mechanism involving the radical Bu3Sn.[3][4]
[edit] See also
[edit] References
- ^ "SnBu3H - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5948.
- ^ Hayashi, K.; Iyoda, J.; Shiihara, I. "Reaction of organotin oxides, alkoxides and acyloxides with organosilicon hydrides. New preparative method of organotin hydrides " J. Organomet. Chem. 1967, 10, 81. doi:10.1016/S0022-328X(00)81719-2
- ^ OUP catalogue page, J. Clayden, N. Greeves, S. Warren and P. Wothers, in Organic Chemistry, 2000, OUP, Oxford, ch. 39, pp. 1040-1041.
- ^ T. V. (Babu) RajanBabu, Philip C. Bulman Page, Benjamin R. Buckley, "Tri-n-butylstannane" Encyclopedia of Reagents for Organic Synthesis 2004, John Wiley & Sons. doi:10.1002/047084289X.rt181.pub2
