Triphenyltin hydride

Triphenyltin hydride is the organotin compound with the formula (C6H5)3SnH. It is a white distillable oil that is soluble in organic solvents. It is often used as a source of "H·" to generate radicals or cleave carbon-oxygen bonds.

Triphenyltin hydride
Skeletal formula of triphenyltin hydride
Space-filling model of the triphenyltin hydride molecule
Names
IUPAC name
Triphenylstannane
Identifiers
3D model (JSmol)
3544353
ChEBI
ChemSpider
ECHA InfoCard 100.011.789
EC Number
  • 212-967-8
6741
RTECS number
  • WH8882000
UNII
  • InChI=1S/3C6H5.Sn.H/c3*1-2-4-6-5-3-1;;/h3*1-5H;; checkY
    Key: NFHRNKANAAGQOH-UHFFFAOYSA-N checkY
  • [H][Sn](C2=CC=CC=C2)(C3=CC=CC=C3)C1=CC=CC=C1
  • c1c(cccc1)[Sn](c2ccccc2)c3ccccc3
Properties
C18H16Sn
Molar mass 351.036 g·mol−1
Appearance colorless
Density 1.374 g/cm3
Melting point 28 °C (82 °F; 301 K)
Boiling point 156 °C (313 °F; 429 K) (0.15 mm Hg)
insoluble
Solubility in benzene, THF soluble
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 toxic
GHS labelling:
GHS06: ToxicGHS09: Environmental hazard
Danger
H301, H311, H331, H410
Flash point >230 °F
Related compounds
Related compounds
 SnCl4,
(C6H5)3SnCl,
(C6H5)3SnOH
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Preparation and reactions

Ph3SnH, as it is more commonly abbreviated, is prepared by treatment of triphenyltin chloride with lithium aluminium hydride.[1] Although Ph3SnH is treated as a source of "H·", in fact it does not release free hydrogen atoms, which are extremely reactive species. Instead, Ph3SnH transfers H to substrates usually via a radical chain mechanism. This reactivity exploits the relatively good stability of "Ph3Sn·"[1]

References
  1. Clive, D. L. J. "Triphenylstannane" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. doi:10.1002/047084289X.rt390
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