Tributyltin hydride
Tributyltin hydride | |
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Systematic name 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 | {{#if:CCCC[SnH](CCCC)CCCC|Image 1 |
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Properties | |
Molecular formula | SnC 12H 28 |
Molar mass | 291.06 g mol-1 |
Density | 1.082 g cm-3 |
Boiling point | 80 °C; 176 °F; 353 K (at 50 Pa) |
Solubility in water | Slowly reacts[citation needed] |
(verify) (what is: / ?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 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.
Synthesis and characterization
The compound is produced by reduction of tributyltin oxide with polymethylhydrosiloxane (Bu = CH3CH2CH2CH2):[2][3]
- 2"(MeSiH)" + (Bu3Sn)2O → "(Me2Si2O" + 2 Bu3SnH
- (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.
Applications
It is a useful reagent in organic synthesis. Combined with azobisisobutyronitrile (AIBN) 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.[4][5]
See also
References
- ↑ "SnBu3H - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information.
- ↑ 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
- ↑ Jordi Tormo and Gregory C. Fu (2002), "Tributylstannane (Bu3SnH)-Catalyzed Barton-McCombie deoxygenation of Alcohols: 3-Deoxy-1,2:5,6-bis-O-(1-methylethyilidine)-α-D-ribo-hexafuranose", Org. Synth. 78: 239
- ↑ 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