Dichlorophenylphosphine

Dichlorophenylphosphine
Preferred IUPAC name Phenylphosphonous dichloride
Other names Dichlorophenylphosphane Phenylphosphorus dichloride
Identifiers
CAS number	644-97-3 Y
PubChem	12573
ChemSpider	12053 Y
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
Density	1.3190 g/mL
Hazards
MSDS	Fisher MSDS
EU classification	Corrosive (C)
NFPA 704	3 0
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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 a 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., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv4p0784 ; Coll. Vol. 4: 784