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

Organic synthesis

Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic molecules can often contain a higher level of complexity compared to purely inorganic compounds, so the synthesis of organic compounds has...

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Synthesis and characterization

The compound is produced by reduction of tributyltin oxide

Tributyltin oxide

Tributyltin oxide , or bisoxide, is an organotin compound chiefly used as a biocide , especially a wood preservative. Its chemical formula is C24H54OSn2. It has the form of a thin, colorless to pale yellow liquid with melting point -45 °C, boiling point 180 °C, and slight water solubility...

 with polymethylhydrosiloxane (Bu = CH₃CH₂CH₂CH₂):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 ν_Sn-H.

Applications

It is a useful reagent in organic synthesis

Organic synthesis

Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic molecules can often contain a higher level of complexity compared to purely inorganic compounds, so the synthesis of organic compounds has...

. 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.