Tetraphenyllead

Last updated
Tetraphenyllead
Tetraphenylblei.svg
Names
IUPAC name
Tetraphenylplumbane
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.976 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 209-871-3
PubChem CID
UNII
  • InChI=1S/4C6H5.Pb/c4*1-2-4-6-5-3-1;/h4*1-5H;
    Key: WBJSMHDYLOJVKC-UHFFFAOYSA-N
  • c1ccccc1[Pb](c2ccccc2)(c3ccccc3)c4ccccc4
Properties
Pb(C6H5)4
Molar mass 515.6 g·mol−1
Appearancewhite powder [1]
Density 1.53 g/cm3 [2]
Melting point 227–228 °C [2]
Boiling point 270 °C (decomposes [3] )
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]
GHS-pictogram-skull.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Danger
H301, H302, H311, H331, H332, H360, H373, H410
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
Other cations
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tetraphenyllead is an organolead compound with the chemical formula Pb(C 6 H 5)4 or PbPh4. It is a white solid.

Contents

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]

References

  1. 1 2 Tetraphenyllead, 97% at AlfaAesar, accessed on 2015-03-27 ( PDF ) (JavaScript required).[ dead link ]
  2. 1 2 3 "Tetraphenyllead". ChemicalBook.
  3. ↑ 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)
  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.
  10. ↑ https://pubchem.ncbi.nlm.nih.gov/compound/Tetraphenyllead
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.