Tetraphenyllead

Tetraphenyllead is an organolead compound with the chemical formula Template:Chem2 or PbPh₄. It is a white solid.

Preparation

Tetraphenyllead can be produced by the reaction of phenylmagnesium bromide and lead chloride at diethyl ether. This is the method used by P. Pfeiffer and P. Truskier to produce tetraphenyllead first at 1904.

$\mathrm{(}{\mathrm{C}}_{\mathrm{6}}{\mathrm{H}}_{\mathrm{5}}\mathrm{)}\mathrm{M}\mathrm{g}\mathrm{B}\mathrm{r}\mathrm{+}\mathrm{2}\mathrm{P}\mathrm{b}\mathrm{C}{\mathrm{l}}_{\mathrm{2}}\underset{E{t}_{2}O}{\overset{}{\to }}\mathrm{P}\mathrm{b}\mathrm{(}{\mathrm{C}}_{\mathrm{6}}{\mathrm{H}}_{\mathrm{5}}{\mathrm{)}}_{\mathrm{4}}\mathrm{+}\mathrm{P}\mathrm{b}\mathrm{+}\mathrm{4}\mathrm{M}\mathrm{g}\mathrm{B}\mathrm{r}\mathrm{C}\mathrm{l}$

Reactions

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

$\mathrm{P}\mathrm{b}\mathrm{(}{\mathrm{C}}_{\mathrm{6}}{\mathrm{H}}_{\mathrm{5}}{\mathrm{)}}_{\mathrm{4}}\mathrm{+}\mathrm{H}\mathrm{C}\mathrm{l}\underset{Ethanol}{\overset{}{\to }}\mathrm{P}\mathrm{b}\mathrm{(}{\mathrm{C}}_{\mathrm{6}}{\mathrm{H}}_{\mathrm{5}}{\mathrm{)}}_{\mathrm{3}}\mathrm{C}\mathrm{l}\mathrm{+}{\mathrm{C}}_{\mathrm{6}}{\mathrm{H}}_{\mathrm{6}}$

$\mathrm{P}\mathrm{b}\mathrm{(}{\mathrm{C}}_{\mathrm{6}}{\mathrm{H}}_{\mathrm{5}}{\mathrm{)}}_{\mathrm{3}}\mathrm{C}\mathrm{l}\mathrm{+}\mathrm{H}\mathrm{C}\mathrm{l}\underset{Ethanol}{\overset{}{\to }}\mathrm{P}\mathrm{b}\mathrm{(}{\mathrm{C}}_{\mathrm{6}}{\mathrm{H}}_{\mathrm{5}}{\mathrm{)}}_{\mathrm{2}}\mathrm{C}{\mathrm{l}}_{\mathrm{2}}\mathrm{+}{\mathrm{C}}_{\mathrm{6}}{\mathrm{H}}_{\mathrm{6}}$

Just like tetrabutyllead, tetraphenyllead and sulfur react explosively at 150 °C and produce diphenyl sulfide and lead sulfide:

$\mathrm{P}\mathrm{b}\mathrm{(}{\mathrm{C}}_{\mathrm{6}}{\mathrm{H}}_{\mathrm{5}}{\mathrm{)}}_{\mathrm{4}}\mathrm{+}\mathrm{3}\mathrm{S}\underset{}{\overset{}{\to }}\mathrm{P}\mathrm{b}\mathrm{S}\mathrm{+}\mathrm{2}\mathrm{S}\mathrm{(}{\mathrm{C}}_{\mathrm{6}}{\mathrm{H}}_{\mathrm{5}}{\mathrm{)}}_{\mathrm{2}}$

Tetraphenyllead reacts with iodine in chloroform to produce triphenyllead iodide.

References

Template:Lead compounds