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Names | |||
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Systematic IUPAC name Tributylstannane | |||
Identifiers | |||
CAS Number | |||
3D model (JSmol) | |||
Beilstein Reference | 3587329 | ||
ChEBI | |||
ChemSpider | |||
ECHA InfoCard | 100.010.642 | ||
EC Number |
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Gmelin Reference | 4258 | ||
MeSH | Tributyltin | ||
PubChem CID | |||
CompTox Dashboard (EPA) | |||
InChI
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SMILES
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Properties | |||
Chemical formula | SnC 12H 28 | ||
Molar mass | 291.06 g mol | ||
Density | 1.082 g cm | ||
Boiling point | 80 °C (176 °F; 353 K) | ||
Solubility in water | Slowly reacts | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) 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):
- (Bu3Sn)2O + 2/n (MeSi(H)O)n → 2 Bu3SnH + 1/n 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 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.
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
- 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