Tributyltin hydride

The compound is used as a source of hydrogen atoms in organic synthesis.

The hydride is a distillable liquid that is mildly sensitive to air, decomposing to (Bu3Sn)2O.

Combined with azobisisobutyronitrile (AIBN) or by irradiation with light, tributyltin hydride converts organic halides (and related groups) to the corresponding hydrocarbon.

[4][5] 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).

Skeletal formula of tributyltin with one explicit hydrogen added
Skeletal formula of tributyltin with one explicit hydrogen added
Spacefill model of tributyltin
Spacefill model of tributyltin
Ball and stick model of tributyltin
Ball and stick model of tributyltin