Tributyltin hydride
Chemical compound
From Wikipedia, the free encyclopedia
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.
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| Names | |||
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| Systematic IUPAC name
Tributylstannane[1] | |||
| Identifiers | |||
3D model (JSmol) |
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| 3587329 | |||
| ChEBI | |||
| ChemSpider | |||
| ECHA InfoCard | 100.010.642 | ||
| EC Number |
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| 4258 | |||
| MeSH | Tributyltin | ||
PubChem CID |
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| UNII | |||
CompTox Dashboard (EPA) |
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| Properties | |||
| 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 | ||
| Slowly reacts[citation needed] | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis and characterization
The compound is produced by reduction of tributyltin oxide with polymethylhydrosiloxane:[2][3]
- 2 "[MeSi(H)O]n" + (Bu3Sn)2O → "[MeSi(OH)O]n" + 2 Bu3SnH
It can also be synthesized by a reduction of tributyltin chloride with lithium aluminium hydride.[4]
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 specialized 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•.[5][6] The radical abstracts a H• from another equivalent of tributyltin hydride, propagating the chain. Tributyltin hydride's utility as a H• donor can be attributed to its relatively weak bond strength (78 kcal/mol).[7]
It is the reagent of choice for hydrostannylation reactions:[8]
- RC2R′ + HSnBu3 → RC(H)=C(SnBu3)R′