Chemistry:Dichlorophenylphosphine

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Dichlorophenylphosphine
Dichlorophenylphosphine-2D-by-AHRLS-2012.png
Dichlorophenylphosphine-3D-balls-by-AHRLS-2012.png
Names
Preferred IUPAC name
Phenylphosphonous dichloride
Other names
Dichlorophenylphosphane
Phenylphosphorus dichloride
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
EC Number
  • 211-425-8
RTECS number
  • TB2478000
UNII
UN number 2798
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
Safety data sheet Fisher MSDS
GHS pictograms GHS05: CorrosiveGHS06: ToxicGHS07: Harmful
GHS Signal word Danger
H290, H301, H302, H314, H335
P234, P260, P261, P264, P270, P271, P280, P301+310, P301+312, P301+330+331, P303+361+353, P304+340, P305+351+338, P310, P312, P321, P330, P363, P390, P403+233, P404, P405, P501
NFPA 704 (fire diamond)
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity code 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 acidNFPA 704 four-colored diamond
1
3
3
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)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Tracking categories (test):

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] 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]

McCormackRxn.png

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