Dichlorophenylphosphine

Dichlorophenylphosphine is an organophosphorus compound with the formula C₆H₅PCl₂. This colourless viscous liquid is commonly used in the synthesis of organophosphines.

Dichlorophenylphosphine

Names
Preferred IUPAC name Phenylphosphonous dichloride
Other names Dichlorophenylphosphane Phenylphosphorus dichloride
Identifiers
CAS Number	644-97-3 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1899635
ChemSpider	12053 Y
ECHA InfoCard	100.010.388
EC Number	211-425-8
PubChem CID	12573
RTECS number	TB2478000
UNII	WRU258L1EW Y
UN number	2798
CompTox Dashboard (EPA)	DTXSID4027282
InChI InChI=1S/C6H5Cl2P/c7-9(8)6-4-2-1-3-5-6/h1-5H Y Key: IMDXZWRLUZPMDH-UHFFFAOYSA-N Y InChI=1/C6H5Cl2P/c7-9(8)6-4-2-1-3-5-6/h1-5H Key: IMDXZWRLUZPMDH-UHFFFAOYAO
SMILES ClP(Cl)c1ccccc1
Properties
Chemical formula	C6H5Cl2P
Molar mass	178.98 g·mol−1
Appearance	colorless liquid
Odor	acrid, pungent
Density	1.3190 g/mL
Melting point	−51 °C (−60 °F; 222 K)
Boiling point	222 °C (432 °F; 495 K)
Solubility in water	insoluble
Solubility	miscible in benzene, CS2, chloroform
Refractive index (nD)	1.6030
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H290, H301, H302, H314, H335
Precautionary statements	P234, P260, P261, P264, P270, P271, P280, P301+P310, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P330, P363, P390, P403+P233, P404, P405, P501
NFPA 704 (fire diamond)	3 1 3 W
Flash point	101 °C (214 °F; 374 K)
Autoignition temperature	159 °C (318 °F; 432 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)	200 mg/kg (oral, rat)
Safety data sheet (SDS)	Fisher MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Dichlorophenylphosphine is commercially available. It may be prepared by an electrophilic substitution of benzene by phosphorus trichloride, catalyzed by aluminium chloride.^[1][2] However, aluminum chloride often induces diarylation; a cleaner catalyst for monoarylation is stannic chloride.^[2] The compound is an intermediate for the synthesis of other chemicals for instance dimethylphenylphosphine:

C₆H₅PCl₂ + 2 CH₃MgI → C₆H₅P(CH₃)₂ + 2 MgICl

Many tertiary phosphines can be prepared by this route.^[3]

In the McCormack reaction dichlorophenylphosphine adds dienes to give the chlorophospholenium ring.^[4]

Reductive coupling of the dichlorophosphine gives the cyclophosphine (PhP)₅.^[5]