Tri-n-butyltin hydride

Tributyltin hydride

Names
Systematic IUPAC name Tributylstannane
Identifiers
CAS Number	688-73-3 Y
3D model (JSmol)	Interactive image
Beilstein Reference	3587329
ChEBI	CHEBI:27086 N
ChemSpider	5734 N
ECHA InfoCard	100.010.642
EC Number	211-704-4
Gmelin Reference	4258
MeSH	Tributyltin
PubChem CID	5948
InChI InChI=1S/3C4H9.Sn.H/c3*1-3-4-2;;/h3*1,3-4H2,2H3;; N Key: DBGVGMSCBYYSLD-UHFFFAOYSA-N N
SMILES CCCC[SnH](CCCC)CCCC
Properties
Chemical formula	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
Solubility in water	Slowly reacts
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
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.

The compound is produced by reduction of tributyltin oxide with polymethylhydrosiloxane (Bu = CH₃CH₂CH₂CH₂):

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.

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.