Tetraphenyl lead

Structural formula
General
Surname	Tetraphenyl lead
other names	Lead tetraphenyl
Molecular formula	C 24 H 20 Pb
Brief description	White dust
External identifiers / databases
CAS number 595-89-1 EC number 209-871-3 ECHA InfoCard 100.008.976 PubChem 72906 Wikidata Q4456660
properties
Molar mass	515.62 g mol −1
Physical state	firmly
density	1.53 g cm −3
Melting point	227-228 ° C
boiling point	270 ° C
solubility	soluble in benzene (15.4 g l −1 , 20 ° C), dioxane (11.4 g l −1 , 20 ° C), CCl 4 (8.04 g l −1 , 20 ° C) insoluble in water
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 360FD-373-410-302-332 P: 260-261-281-304 + 340-405-501
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tetraphenyl lead is a chemical compound from the group of organic lead compounds . The white solid is relatively good in organic solvents and almost insoluble in water.

Extraction and presentation

The preparation of tetraphenyl lead by reacting the Grignard reagent phenylmagnesium bromide with lead (II) chloride in diethyl ether was first reported in 1904 by P. Pfeiffer and P. Truskier.

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

properties

By reacting tetraphenyl lead with an alcoholic hydrogen chloride solution, phenyl groups can be successively replaced by chloride ions with the formation of benzene :

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

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

Like the homologous tetrabutyl lead , tetraphenyl lead also reacts explosively with elemental sulfur at temperatures above 150 ° C to form diphenyl sulfide and lead sulfide :

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

use

Triphenyl lead iodide can be obtained by reaction with iodine in chloroform .

Individual evidence

1. ↑ ^{a b c d e} data sheet Tetraphenyllead, 97% at AlfaAesar, accessed on March 27, 2015 ( PDF )(JavaScript required) .
2. ↑ ^{a b c} Entry on tetraphenyl lead in ChemicalBook , accessed March 25, 2015.
3. ↑ Walter Strohmeier, Karlheinz Miltenberger: Note on the solubilities of tetraphenylmethane tetraphenyl-silicon, -germanium, -tin and -lead in organic solvents . In: Chemical Reports . tape 91 , no. 6 , June 1958, p. 1357 , doi : 10.1002 / cber.19580910638 .
4. ↑ P. Pfeiffer, P. Truskier: For the representation of organic lead and mercury compounds . In: Reports of the German Chemical Society . tape 37 , no. 1 , January 1904, p. 1125 , doi : 10.1002 / cber.190403701183 .
5. ^ F. Just: Chemisches Colloquium der Universität Berlin . In: Angewandte Chemie . tape 59 , no. 5-6 , May 1947, pp. 176 , doi : 10.1002 / anie.19470590510 (Original title: Investigations on organic lead and organotin compounds .).
6. ^ Max Schmidt, Herbert Schumann: Cleavage reactions of organometallic compounds with chalcogens. Reactions of sulfur with organosilicon, germanium and lead organic compounds . In: Journal of Inorganic and General Chemistry . tape 325 , no. 3-4 , October 1963, ISSN  0044-2313 , pp. 130 , doi : 10.1002 / zaac.19633250305 .
7. ^ Richard W. Weiss: Compounds of Germanium, Tin, and Lead, including Biological Activity and Commercial Application Covering the Literature from 1937 to 1964 . Springer Science & Business Media, 2013, ISBN 978-3-642-51889-8 , pp. 555 ( limited preview in Google Book search).