Dichlorophenylphosphine

Dichlorophenylphosphine
Names
	Preferred IUPAC name Phenylphosphonous dichloride
	Other names Dichlorophenylphosphane; Phenylphosphorus dichloride
Identifiers
CAS Number	644-97-3 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1899635;
ChemSpider	12053 ;
ECHA InfoCard	100.010.388
EC Number	211-425-8;
PubChem CID	12573;
RTECS number	TB2478000;
UNII	WRU258L1EW ;
UN number	2798
CompTox Dashboard (EPA)	DTXSID4027282 ;
	InChI InChI=1S/C6H5Cl2P/c7-9(8)6-4-2-1-3-5-6/h1-5H Key: IMDXZWRLUZPMDH-UHFFFAOYSA-N ; 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). verify (what is ?) Infobox references

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

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]

References

^ B. Buchner; L. B. Lockhart, Jr. (1951). "Phenyldichlorophosphine". Organic Syntheses. 31: 88. doi:10.15227/orgsyn.031.0088.
^ ^a ^b Engel, Robert; Cohen, Jaime-Lee Iolani (2004). Synthesis of Carbon–Phosphorus Bonds (2 ed.). CRC. §6.2.3. ISBN 0-8493-1617-0.
^ P. Loeliger E. Flückiger (1976). "Sulfide Contraction via Alkylative Coupling: 3-Methyl-2,4-heptanedione". Organic Syntheses. 55: 127. doi:10.15227/orgsyn.055.0127.
^ W. B. McCormack (1963). "3-Methyl-1-Phenylphospholene oxide". Org. Synth. 43: 73. doi:10.15227/orgsyn.043.0073.
^ Marianne Baudler, Klaus Glinka (1993). "Monocyclic and Polycyclic Phosphines". Chem. Rev. 93: 1623–1667. doi:10.1021/cr00020a010.

[1] B. Buchner; L. B. Lockhart, Jr. (1951). "Phenyldichlorophosphine". Organic Syntheses. 31: 88. doi:10.15227/orgsyn.031.0088.

[ECSynth-2] Engel, Robert; Cohen, Jaime-Lee Iolani (2004). Synthesis of Carbon–Phosphorus Bonds (2 ed.). CRC. §6.2.3. ISBN 0-8493-1617-0.

[3] P. Loeliger E. Flückiger (1976). "Sulfide Contraction via Alkylative Coupling: 3-Methyl-2,4-heptanedione". Organic Syntheses. 55: 127. doi:10.15227/orgsyn.055.0127.

[4] W. B. McCormack (1963). "3-Methyl-1-Phenylphospholene oxide". Org. Synth. 43: 73. doi:10.15227/orgsyn.043.0073.

[5] Marianne Baudler, Klaus Glinka (1993). "Monocyclic and Polycyclic Phosphines". Chem. Rev. 93: 1623–1667. doi:10.1021/cr00020a010.

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