Chlorine (diphenyl) phosphine

Structural formula
General
Surname	Chlorine (diphenyl) phosphine
other names	Chlorodiphenylphosphine P -chlorodiphenylphosphine Diphenylphosphine chloride Phosphenyl chloride
Molecular formula	C 12 H 10 ClP
Brief description	colorless liquid with an unpleasant odor
External identifiers / databases
CAS number 1079-66-9 EC number 214-093-2 ECHA InfoCard 100.012.813 PubChem 66180 Wikidata Q411681
properties
Molar mass	220.64 g · mol -1
Physical state	liquid
density	1.2 g cm −3 (20 ° C)
Melting point	14-16 ° C
boiling point	320 ° C
Vapor pressure	1.3 h Pa (20 ° C)
solubility	violent decomposition with water
Refractive index	1.634
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 290-302-314-412 EUH: 014 P: 280-301 + 330 + 331-303 + 361 + 353-305 + 351 + 338-310
Toxicological data	360 mg kg −1 ( LD 50 ,  rat ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Chlorodiphenylphosphine is a chemical compound belonging to the group of phosphines . It has two phenyl radicals and a chlorine atom attached to the central phosphorus .

Manufacturing

Technically, the synthesis of chlorodiphenylphosphine can be accomplished by the disproportionation of dichlorophenylphosphine at temperatures above 280 ° C in the gas phase .

${\displaystyle \mathrm {2\ Cl_{2}PPh\longrightarrow \ ClPPh_{2}\ +\ PCl_{3}} }$

Disproportionation of dichlorophenylphosphine into chlorodipenylphosphine and phosphorus trichloride. Ph = phenyl

The large-scale synthesis takes place via the reaction of phosphorus trichloride with benzene at 600 ° C., whereby dichlorophenylphosphine is formed first, which disproportionates to chlorodiphenylphosphine in the reaction shown above.

For example, the reaction of phosphorus trichloride with a Grignard reagent (e.g. phenylmagnesium bromide) and also with phenylzinc chloride (PhZnCl) or diphenylmercury (Ph ₂ Hg) can be used for production on a laboratory scale .

${\displaystyle \mathrm {PCl_{3}\ +\ 2\ PhZnCl\longrightarrow \ ClPPh_{2}\ +\ 2\ ZnCl_{2}} }$

Phosphorus trichloride reacts with phenylzinc chloride to form chlorodiphenylphosphine and zinc chloride .

Another way is to react triphenylphosphine with molecular chlorine.

${\displaystyle \mathrm {PPh_{3}\ +\ Cl_{2}\longrightarrow \ ClPPh_{2}\ +\ PhCl} }$

Triphenylphosphine reacts with chlorine to form chlorophenylphosphine and chlorobenzene .

properties

Chlorodiphenylphosphine is a corrosive liquid that solidifies below a temperature of 14 to 16 ° C. It reacts violently with water to form hydrogen chloride .

use

The compound has a leaving group with the chlorine atom , which means that nucleophilic substitutions can be carried out on it. By using Grignard reagents as nucleophiles , alkylated and arylated phosphines are accessible.

It is used to phosphine ligand as dppm and dppp produce.

Individual evidence

1. ↑ ^{a b c d e f g h} Entry on diphenylphosphine chloride in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
2. ↑ ^{a b} Th. Weil: About Diarylchlorphosphine , in: Helv. Chim. Acta , 1954 , 37 (2) , pp. 654-655.
3. ↑ Data chlorine (diphenyl) phosphine (PDF) at Merck , accessed March 4, 2010 .
4. ↑ A. Broglie: About the behavior of phosphenyl chloride at higher temperatures , in: Chem. Ber. , 1877 , 21 , p. 628.
5. ↑ J. Svara, N. Weferling, T. Hofmann: Organic Phosphorus Compounds in: Ullmann's Encyclopedia of Industrial Chemistry , 7th edition, John Wiley & Sons., 2008
6. ↑ A. Michaelis, H. v. Soden: About tripenylphosphine and some derivatives of the same , in: Liebigs Ann. , 1885 , 229 (3) , pp. 295-334.