Tetraphenyllead

Tetraphenyllead is an organolead compound with the chemical formula Pb(C₆H₅)₄ or PbPh₄. It is a white solid.

Tetraphenyllead

Names
IUPAC name Tetraphenylplumbane
Identifiers
CAS Number	595-89-1 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:30184
ChemSpider	65738
ECHA InfoCard	100.008.976
EC Number	209-871-3
PubChem CID	72906
UNII	2K9SW63R4N
CompTox Dashboard (EPA)	DTXSID20208203
InChI InChI=1S/4C6H5.Pb/c4*1-2-4-6-5-3-1;/h4*1-5H; Key: WBJSMHDYLOJVKC-UHFFFAOYSA-N
SMILES c1ccccc1[Pb](c2ccccc2)(c3ccccc3)c4ccccc4
Properties
Chemical formula	Pb(C6H5)4
Molar mass	515.6 g·mol−1
Appearance	white powder[1]
Density	1.53 g/cm3[2]
Melting point	227–228 °C[2]
Boiling point	270 °C (decomposes[3])
Solubility in water	insoluble[1]
Solubility	benzene 15.4 g/L dioxane 11.4 g/L carbon tetrachloride 8.04 g/L[4]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	May cause damage to the organs and the unborn child
GHS labelling:[5]
Pictograms
Signal word	Danger
Hazard statements	H301, H302, H311, H331, H332, H360, H373, H410
Precautionary statements	P203, P260, P261, P262, P264, P270, P271, P273, P280, P301+P316, P301+P317, P302+P352, P304+P340, P316, P317, P318, P319, P321, P330, P361+P364, P391, P403+P233, P405, P501
Flash point	126 °C (13 mmHg)[2]
Related compounds
Other anions	Tetramethyllead Tetraethyllead Tetrabutyllead
Other cations	Tetraphenylmethane Tetraphenylsilane Tetraphenylgermanium Tetraphenyltin
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Preparation

Tetraphenyllead can be produced by the reaction of phenylmagnesium bromide and lead(II) chloride in diethyl ether. This was the method first used by P. Pfeiffer and P. Truskier to produce tetraphenyllead in 1904.^[6]

(C₆H₅)MgBr + 2 PbCl₂ → Pb(C₆H₅)₄ + Pb + 4 MgBrCl

Reactions

A solution of hydrogen chloride in ethanol can react with tetraphenyllead and substitute some of the phenyl groups to chlorine atoms:^[7]

Pb(C₆H₅)₄ + HCl → Pb(C₆H₅)₃Cl + C₆H₆

Pb(C₆H₅)₃Cl + HCl → Pb(C₆H₅)₂Cl₂ + C₆H₆

Just like tetrabutyllead, tetraphenyllead and sulfur react explosively at 150 °C and produce diphenyl sulfide and lead(II) sulfide:^[8]

Pb(C₆H₅)₄ + 3 S → PbS + 2 S(C₆H₅)₂

Tetraphenyllead reacts with iodine in chloroform to produce triphenyllead iodide.^[9]

Safety

Tetraphenyllead may damage fertility or the unborn child, to organs through prolonged or repeated exposure (kidneys, male gonads, liver, central nervous system). Possible carcinogen.^[10]