|Systematic IUPAC name
|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|
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
|what is: / ?)(|
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 & Characterization
- 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.
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. 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). Recently, transition metal hydrides have emerged as attractive alternatives to tin hydrides, as transition metal hydrides can be used catalytically and have more variety in bond strength.
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