Phenylthiophosphonyl dichloride

Structural formula
General
Surname	Phenylthiophosphonyl dichloride
other names	Dichlorophenylphosphine sulfide DCPPS
Molecular formula	C 6 H 5 Cl 2 PS
Brief description	colorless liquid
External identifiers / databases
CAS number 3497-00-5 EC number 222-494-9 ECHA InfoCard 100.020.451 PubChem 19016 Wikidata Q1419323
properties
Molar mass	211 g mol −1
Physical state	liquid
density	1.4 g cm −3
Melting point	118 ° C
boiling point	270 ° C
Refractive index	1.6178-1.6182
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 290-302 + 312 + 332-314 P: ?
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

Phenylthiophosphonyl dichloride is an aromatic chemical compound from the groups of organophosphorus compounds and thiophosphoric acid esters .

Extraction and presentation

To produce phenylthiophosphonyl dichloride, benzene is first reacted with phosphorus trichloride in the presence of aluminum chloride. The reaction with elemental sulfur then forms phenylthiophosphonyl dichloride.

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

${\displaystyle \mathrm {PhPCl_{2}\ +S\ {\xrightarrow {\ }}\ PhCl_{2}PS} }$

Reaction of phosphorus trichloride with benzene to form dichlorophenylphosphine, then with sulfur to form phenylthiophosphonyl dichloride (Ph = phenyl).

use

Phenylthiophosphonyl dichloride is an intermediate in the synthesis of the insecticide EPN .

The compound can be used as a starting material for the production of bis (4-carboxyphenyl) phenylphosphine oxide , which was investigated as a comonomer for nylon with higher flame retardancy .

Individual evidence

1. ↑ ^{a b c d e} Entry on Phenylthiophosphononic dichloride at ChemicalBook , accessed on April 18, 2012.
2. ↑ There is not yet a harmonized classification for this substance . A labeling of dichloro (phenyl) phosphine sulphide in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on November 5, 2019, is reproduced from a self-classification by the distributor .
3. ↑ Patent US2961405 : Lubricating compositions containing phosphorus compounds for lubrication of silver bearings. Applied on February 17, 1956 , published November 22, 1960 , applicant: Shell Oil, inventor: Richard G. Cunningham. ‌
4. ↑ Thomas A. Unger: Pesticide synthesis handbook. 1996, ISBN 978-0-81551401-5 , p. 284 ( limited preview in Google book search).
5. ^ I-Yuan Wan, JE McGrath, Takashi Kashiwagi: Triarylphosphine Oxide Containing Nylon 6,6 Copolymers. In: Fire and Polymers II. Chapter 2, pp. 29-40, doi : 10.1021 / bk-1995-0599.ch002 ( online ; PDF; 562 kB).