Chemistry:Triphenyltin hydride

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
EC Number	212-967-8
Gmelin Reference	6741
PubChem CID	6460
RTECS number	WH8882000
UNII	95T92AGN0V Y
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
Main hazards	toxic
GHS pictograms
GHS Signal word	Danger
GHS 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).
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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.

Preparation and reactions

Ph₃SnH, as it is more commonly abbreviated, is prepared by treatment of triphenyltin chloride with lithium aluminium hydride. 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·"