Triphenyltin hydride

Triphenyltin hydride is the organotin compound with the formula (C₆H₅)₃SnH. It is a colorless 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

Names
IUPAC name Triphenylstannane
Identifiers
CAS Number	892-20-6 Y
3D model (JSmol)	Interactive image Interactive image
Beilstein Reference	3544353
ChEBI	CHEBI:30537 Y
ChemSpider	6217 Y
ECHA InfoCard	100.011.789
EC Number	212-967-8
Gmelin Reference	6741
PubChem CID	6460
RTECS number	WH8882000
UNII	95T92AGN0V Y
CompTox Dashboard (EPA)	DTXSID40893312
InChI InChI=1S/3C6H5.Sn.H/c3*1-2-4-6-5-3-1;;/h3*1-5H;; Y Key: NFHRNKANAAGQOH-UHFFFAOYSA-N Y
SMILES [H][Sn](C2=CC=CC=C2)(C3=CC=CC=C3)C1=CC=CC=C1 c1c(cccc1)[Sn](c2ccccc2)c3ccccc3
Properties
Chemical formula	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)
Solubility in water	insoluble
Solubility in benzene, THF	soluble
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	toxic
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	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). Y verify (what is YN ?) 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]