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Dichlorophenylphosphine

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(Redirected from Phenyldichlorophosphine)
Dichlorophenylphosphine
Names
Preferred IUPAC name Phenylphosphonous dichloride
Other names Dichlorophenylphosphane
Phenylphosphorus dichloride
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.010.388 Edit this at Wikidata
EC Number
  • 211-425-8
PubChem CID
RTECS number
  • TB2478000
UNII
UN number 2798
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H5Cl2P/c7-9(8)6-4-2-1-3-5-6/h1-5HKey: IMDXZWRLUZPMDH-UHFFFAOYSA-N
  • InChI=1/C6H5Cl2P/c7-9(8)6-4-2-1-3-5-6/h1-5HKey: IMDXZWRLUZPMDH-UHFFFAOYAO
SMILES
  • ClP(Cl)c1ccccc1
Properties
Chemical formula C6H5Cl2P
Molar mass 178.98 g·mol
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 GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation mark
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)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxideSpecial hazard W: Reacts with water in an unusual or dangerous manner. E.g. sodium, sulfuric acid
3 1 3W
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 , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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. However, aluminum chloride often induces diarylation; a cleaner catalyst for monoarylation is stannic chloride. 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.

In the McCormack reaction dichlorophenylphosphine adds dienes to give the chlorophospholenium ring.

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

References

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