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Dichlorophenylphosphine

Summary

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
  • 644-97-3 checkY
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL1899635
ChemSpider
  • 12053 checkY
ECHA InfoCard 100.010.388 Edit this at Wikidata
EC Number
  • 211-425-8
  • 12573
RTECS number
  • TB2478000
UNII
  • WRU258L1EW checkY
UN number 2798
  • DTXSID4027282 Edit this at Wikidata
  • InChI=1S/C6H5Cl2P/c7-9(8)6-4-2-1-3-5-6/h1-5H checkY
    Key: IMDXZWRLUZPMDH-UHFFFAOYSA-N checkY
  • InChI=1/C6H5Cl2P/c7-9(8)6-4-2-1-3-5-6/h1-5H
    Key: IMDXZWRLUZPMDH-UHFFFAOYAO
  • ClP(Cl)c1ccccc1
Properties
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)
insoluble
Solubility miscible in benzene, CS2, chloroform
1.6030
Hazards
GHS labelling:
GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation mark
Danger
H290, H301, H302, H314, H335
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
3
W
Flash point 101 °C (214 °F; 374 K)
159 °C (318 °F; 432 K)
Lethal dose or concentration (LD, LC):
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).
checkY verify (what is checkY☒N ?)
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]

References edit

  1. ^ B. Buchner; L. B. Lockhart, Jr. (1951). "Phenyldichlorophosphine". Organic Syntheses. 31: 88. doi:10.15227/orgsyn.031.0088.
  2. ^ 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.
  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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