Chlorodiphenylphosphine

Chlorodiphenylphosphine

Names
Preferred IUPAC name Diphenylphosphinous chloride
Other names chlorodiphenylphosphine p-chlorodiphenylphosphine diphenyl phosphine chloride diphenylchlorophosphine
Identifiers
CAS Number	1079-66-9 Y
3D model (Jmol)	Interactive image
ChemSpider	59567 Y
ECHA InfoCard	100.012.813
UNII	WO975PJK1Y N
InChI InChI=1S/C12H10ClP/c13-14(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H Y Key: XGRJZXREYAXTGV-UHFFFAOYSA-N Y InChI=1/C12H10ClP/c13-14(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H Key: XGRJZXREYAXTGV-UHFFFAOYAM
SMILES ClP(c1ccccc1)c2ccccc2
Properties
Chemical formula	C12H10ClP
Molar mass	220.63776 g mol−1
Appearance	clear to light yellow liquid
Density	1.229 g cm−3
Boiling point	320 ˚C
Solubility in water	Reacts
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Chlorodiphenylphosphine is an organophosphorus compound with the formula (C₆H₅)₂PCl, abbreviated Ph₂PCl. It is a colourless oily liquid with a pungent odor that is often described as being garlic-like and detectable even in the ppb range. It is useful reagent for introducing the Ph₂P group into molecules, which includes many ligands. Like other halophosphines, Ph₂PCl is reactive with many nucleophiles such as water and easily oxidized even by air.

Chlorodiphenylphosphine is produced on a commercial scale from benzene and phosphorus trichloride (PCl₃). Benzene reacts with phosphorus trichloride at extreme temperatures around 600 °C to give dichlorophenylphosphine (PhPCl₂). Redistribution of PhPCl₂ in the gas phase at high temperatures results in chlorodiphenylphosphine.

Alternatively such compounds are prepared by redistribution reactions starting with triphenylphosphine and phosphorus trichloride. Synthesis of Ph₂PCl by the direct reaction of phenylmagnesium bromide and phosphorus trichloride is not practiced. On the other hand, PCl₃ can be usefully converted to its monoamide, which in turn undergoes alkylation or arylation. Subsequent removal of the amide gives :

Unlike the synthesis of chlorodiisopropylphosphine, reaction of two equivalents of the phenyl Grignard reagents with PCl₃ does not efficiently afford the monochloride.

Chlorodiphenylphosphine hydrolyzes to give diphenylphosphine oxide. With amines, it forms the amides Ph₂PNR₂.