Dichlorophenylphosphine

Dichlorophenylphosphine
Preferred IUPAC name Phenylphosphonous dichloride
Other names Dichlorophenylphosphane Phenylphosphorus dichloride
Identifiers
CAS number	644-97-3 Y
PubChem	12573
ChemSpider	12053 Y
RTECS number	TB2478000
Jmol-3D images	Image 1
SMILES ClP(Cl)c1ccccc1
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
Properties
Molecular 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
MSDS	Fisher MSDS
EU classification	Corrosive (C)
NFPA 704	1 3 3 W
Flash point	101 °C; 214 °F; 374 K
Autoignition temperature	159 °C; 318 °F; 432 K
LD50	200 mg/kg (oral, rat)
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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

Dichlorophenylphosphine is commercially available. It may be prepared by an electrophilic substitution of benzene by phosphorus trichloride, catalyzed by aluminium chloride.^[1] The compound is an intermediate for the synthesis of other chemicals for instance dimethylphenylphosphine:

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

Dichlorophenylphosphine undergoes the McCormack reaction upon treatment with dienes to give phospholes.

References

1. ↑ B. Buchner and L. B. Lockhart, Jr. (1963), "Phenyldichlorophosphine", Org. Synth. ; Coll. Vol. 4: 784