Tetraphenyllead

Tetraphenyllead

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
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	C24H20Pb
Molar mass	515.6 g·mol−1
Appearance	white powder [1]
Density	1.53 g·cm−3 [2]
Melting point	227–228 °C [2]
Boiling point	270 °C (decomposes [3] )
Solubility in water	insoluble [1]
Solubility	benzene 15.4 g·l−1 dioxane 11.4 g·l−1 carbon tetrachloride 8.04 g·l−1 [4]
Hazards
GHS labelling: [5]
Pictograms
Signal word	Danger
Hazard statements	H302, H332, H360, H373, H410
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

Tetraphenyllead is an organolead compound with the chemical formula (C₆H₅)₄Pb 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 was the method first used by P. Pfeiffer and P. Truskier to produce tetraphenyllead in 1904. ^[6]

${\displaystyle \mathrm {(C_{6}H_{5})MgBr+\ 2\ PbCl_{2}\ {\xrightarrow[{Et_{2}O}]{}}\ Pb(C_{6}H_{5})_{4}+\ Pb+\ 4\ MgBrCl} }$

Reactions

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

${\displaystyle \mathrm {Pb(C_{6}H_{5})_{4}+\ HCl\ {\xrightarrow[{Ethanol}]{}}\ Pb(C_{6}H_{5})_{3}Cl+\ C_{6}H_{6}} }$

${\displaystyle \mathrm {Pb(C_{6}H_{5})_{3}Cl+\ HCl\ {\xrightarrow[{Ethanol}]{}}\ Pb(C_{6}H_{5})_{2}Cl_{2}+\ C_{6}H_{6}} }$

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

${\displaystyle \mathrm {Pb(C_{6}H_{5})_{4}+\ 3\ S\ {\xrightarrow[{}]{}}\ PbS+\ 2\ S(C_{6}H_{5})_{2}} }$

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

References

1. Tetraphenyllead, 97% at AlfaAesar, accessed on 2015-03-27 ( PDF ) (JavaScript required).^{[ dead link ‍]}
2. "Tetraphenyllead". ChemicalBook.
3. Greenwood, N. N.; Earnshaw, A. (1997). Chemistry of the elements. Boston, Mass. p. 404. ISBN   0-585-37339-6. OCLC   48138330.
4. Walter Strohmeier, Karlheinz Miltenberger (June 1958). "Notiz über die Löslichkeiten von Tetraphenylmethan Tetraphenyl-silicium, -germanium, -zinn und -blei in organischen Lösungsmitteln". Chemische Berichte (in German). 91 (6): 1357. doi:10.1002/cber.19580910638.
5. "Tetraphenyllead". pubchem.ncbi.nlm.nih.gov.
6. P. Pfeiffer, P. Truskier (January 1904). "Zur Darstellung organischer Blei- und Quecksilber-Verbindungen". Berichte der Deutschen Chemischen Gesellschaft (in German). 37: 1125. doi:10.1002/cber.190403701183.
7. F. Just (May 1947). "Chemisches Colloquium der Universität Berlin". Angewandte Chemie (in German). 59 (5–6): 176. Bibcode:1947AngCh..59..161J. doi:10.1002/ange.19470590510.
8. Max Schmidt, Herbert Schumann (October 1963). "Spaltungsreaktionen metallorganischer Verbindungen mit Chalkogenen. Reaktionen von Schwefel mit silicium-, germanium- und bleiorganischen Verbindungen". Zeitschrift für Anorganische und Allgemeine Chemie (in German). 325 (3–4): 130. doi:10.1002/zaac.19633250305. ISSN   0044-2313.
9. Richard W. Weiss (2013). Compounds of Germanium, Tin, and Lead, including Biological Activity and Commercial Application Covering the Literature from 1937 to 1964. Springer Science & Business Media. p. 555. ISBN   978-3-642-51889-8.