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.
|Preferred IUPAC name
diphenyl phosphine chloride
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||220.63776 g mol−1|
|Appearance||clear to light yellow liquid|
|Density||1.229 g cm−3|
|Boiling point||320 ˚C|
|Solubility||Reacts with alcohols|
highly soluble in benzene, THF, and ethers
|H290, H302, H314, H412|
|P234, P260, P264, P270, P273, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P390, P404, P405, P501|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
(what is ?)
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) and HCl. Redistribution of PhPCl2 in the gas phase at high temperatures results in chlorodiphenylphosphine.
With ammonia and elemental sulfur, it converts to the thiophosphorylamide:
The phosphines produced from reactions with Ph2PCl are further developed and used as pesticides (such as EPN), stabilizers for plastics (Sandostab P-EPQ), various halogen compound catalysts, flame retardants (cyclic phosphinocarboxylic anhydride), as well as UV-hardening paint systems (used in dental materials) making Ph2PCl an important intermediate in the industrial world.
Both Ph2PNa and Ph2PH are also used in the synthesis of organophosphine ligands.
|Compound||31P chemical shift
(ppm vs 85% H3PO4)