Tetraphenyllead
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3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.008.976 |
| EC Number |
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| 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]) |
| 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] | |
   
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| Danger | |
| H302, H332, H360, H373, H410 | |
| Related compounds | |
Other anions
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Tetramethyllead Tetraethyllead Tetrabutyllead |
Other cations
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Tetraphenylmethane Tetraphenylsilane Tetraphenylgermanium Tetraphenyltin |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Tetraphenyllead is an organolead compound with the chemical formula (C6H5)4Pb or PbPh4. It is a white solid.
Preparation
[edit]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.[6]
![{\displaystyle \mathrm {(C_{6}H_{5})MgBr+\ 2\ PbCl_{2}\ {\xrightarrow[{Et_{2}O}]{}}\ Pb(C_{6}H_{5})_{4}+\ Pb+\ 4\ MgBrCl} }](https://wikimedia.org/api/rest_v1/media/math/render/svg/a68a002fb9900cd1c48b06092065ba8cde358c05)
Reactions
[edit]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}} }](https://wikimedia.org/api/rest_v1/media/math/render/svg/2417302affebdbea4b3f34bc6fc75d673f1ad62d)
![{\displaystyle \mathrm {Pb(C_{6}H_{5})_{3}Cl+\ HCl\ {\xrightarrow[{Ethanol}]{}}\ Pb(C_{6}H_{5})_{2}Cl_{2}+\ C_{6}H_{6}} }](https://wikimedia.org/api/rest_v1/media/math/render/svg/5fbdfb1f11bde306d1775ec460db04f257f26fd8)
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}} }](https://wikimedia.org/api/rest_v1/media/math/render/svg/aa19921cfbe9c8890ff58c0053fbc5c037b79041)
Tetraphenyllead reacts with iodine in chloroform to produce triphenyllead iodide.[9]
References
[edit]- ^ a b Tetraphenyllead, 97% at AlfaAesar, accessed on 2015-03-27 (PDF) (JavaScript required).[dead link]
- ^ a b "Tetraphenyllead". ChemicalBook.
- ^ Greenwood, N. N.; Earnshaw, A. (1997). Chemistry of the elements. Boston, Mass. p. 404. ISBN 0-585-37339-6. OCLC 48138330.
{{cite book}}: CS1 maint: location missing publisher (link) - ^ 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.
- ^ "Tetraphenyllead". pubchem.ncbi.nlm.nih.gov.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.