Dichloro (phenyl) phosphine

Structural formula
General
Surname	Dichloro (phenyl) phosphine
other names	Dichloro (phenyl) phosphine Dichlorophenylphosphine Phenyl dichlorophosphine Phenyl phosphorus dichloride
Molecular formula	C 6 H 5 Cl 2 P
Brief description	colorless liquid with a pungent odor
External identifiers / databases
CAS number 644-97-3 EC number 211-425-8 ECHA InfoCard 100.010.388 PubChem 12573 Wikidata Q410415
properties
Molar mass	178.99 g · mol -1
Physical state	liquid
density	1.32 g cm −3 (20 ° C)
Melting point	−51 ° C
boiling point	225 ° C
solubility	Decomposes with water, miscible with benzene , chloroform and carbon disulphide
Refractive index	1.5962
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 301-314-335 EUH: 014 P: 280-301 + 310 + 330-303 + 361 + 353-304 + 340 + 310-305 + 351 + 338
Toxicological data	200 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

Dichlorophenylphosphine is a chemical compound from the group of phosphines . It has a phenyl residue and two chlorine atoms attached to the central phosphorus .

Manufacturing

The reaction between phosphorus trichloride and benzene in the presence of aluminum chloride can be used to synthesize dichlorophenylphosphine . The reaction proceeds analogously to a Friedel-Crafts acylation . The Lewis acid aluminum chloride first activates phosphorus trichloride and thus enables the subsequent electrophilic attack on the benzene.

${\displaystyle \mathrm {PCl_{3}\ +\ C_{6}H_{6}\ {\xrightarrow {[AlCl_{3}]}}\ \ PhPCl_{2}+HCl\uparrow } }$

Reaction of phosphorus trichloride with benzene to form dichlorophenylphosphine. Ph = phenyl. The hydrogen chloride formed as a by-product escapes from the reaction mixture as a gas.

properties

Dichlorophenylphosphine is a colorless liquid with a pungent odor with a melting point of −51 ° C and a boiling point of 225 ° C. It decomposes with water to form hydrogen chloride .

use

Dichloride can be used for synthesis of chlorodiphenylphosphane be used. At temperatures above 280 ° C, dichlorophenylphosphine disproportionates to chlorodiphenylphosphine and phosphorus trichloride.

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

Disproportionation of dichlorophenylphosphine into chlorodipenylphosphine and phosphorus trichloride.

Reduction of the compound using lithium aluminum hydride in diethyl ether gives the phenylphosphine .

${\displaystyle \mathrm {2\ C_{6}H_{5}PCl_{2}\ +\ LiAlH_{4}\longrightarrow \ C_{6}H_{5}PH_{2}\ +\ LiAlCl_{4}} }$

Individual evidence

1. ↑ ^{a b c d e f g} Entry on dichloro (phenyl) phosphine in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .
2. ↑ A. Michaelis: About the compounds of the elements of the nitrogen group with the radicals of the aromatic series . In: Justus Liebig's Annals of Chemistry . tape 181 , no. 3 , 1876, p. 265-363 , doi : 10.1002 / jlac.18761810302 .
3. ^ Georg Wittig, Helmut Braun, Henri-Jean Cristau: Presentation and resolution of chiral triarylphosphines . In: Justus Liebig's Annals of Chemistry . tape 751 , no. 1 , October 12, 1971, p. 17-26 , doi : 10.1002 / jlac.19717510103 .
4. ↑ Data sheet dichlorophenylphosphine (PDF) from Merck , accessed on March 24, 2011.
5. ^ F Simeon, P.-A Jaffres, D Villemin: A direct and new convenient oxidation: synthesis of substituted arylphosphonates from aromatics . In: Tetrahedron . tape 54 , no. 34 , 1998, pp. 10111-10118 .
6. ↑ A. Broglie: About the behavior of phosphenyl chloride at higher temperatures . In: Reports of the German Chemical Society . tape 10 , no. 1 , 1877, p. 628 , doi : 10.1002 / cber.187701001174 .
7. ↑ Leon D. Freedman, GO Doak: The Reduction of Benzenephosphonyl Dichloride . In: Journal of the American Chemical Society . tape 74 , no. July 13 , 1952, p. 3414–3415 , doi : 10.1021 / ja01133a504 .