“Dichlorophenylphosphine”的意思、由来-开放百科全书

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Dichlorophenylphosphine

释义

References

{{chembox
| Watchedfields = changed
| verifiedrevid = 413715098
| ImageFile1=Dichlorophenylphosphine-2D-by-AHRLS-2012.png
| ImageSize1=150px
| ImageFile2=Dichlorophenylphosphine-3D-balls-by-AHRLS-2012.png
| ImageSize2=150px
| PIN=Phenylphosphonous dichloride
| OtherNames=Dichlorophenylphosphane
Phenylphosphorus dichloride
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 12053
| InChI = 1/C6H5Cl2P/c7-9(8)6-4-2-1-3-5-6/h1-5H
| InChIKey = IMDXZWRLUZPMDH-UHFFFAOYAO
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H5Cl2P/c7-9(8)6-4-2-1-3-5-6/h1-5H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = IMDXZWRLUZPMDH-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=644-97-3
| PubChem=12573
| RTECS = TB2478000
| SMILES = ClP(Cl)c1ccccc1
}}
|Section2={{Chembox Properties
| C=6 | H=5 | Cl=2 | P=1
| Appearance= colorless liquid
| Odor = acrid, pungent
| Density=1.3190 g/mL
| MeltingPtC= -51
| BoilingPtC= 222
| Solubility= insoluble
| SolubleOther = miscible in benzene, CS₂, chloroform
| RefractIndex = 1.6030
|Section3={{Chembox Hazards
| ExternalSDS = [https://fscimage.fishersci.com/msds/24901.htm Fisher MSDS]
| NFPA-H = 3 | NFPA-F = 1 | NFPA-R = 3 | NFPA-S = W
| EUClass = Corrosive (C)
| FlashPtC = 101
| AutoignitionPtC = 159
| LD50 = 200 mg/kg (oral, rat)
}}

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 an 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

In the McCormack reaction dichlorophenylphosphine adds dienes to give the chlorophospholenium ring.^[2]

References

1. ^{{OrgSynth | author = B. Buchner and L. B. Lockhart, Jr. | title = Phenyldichlorophosphine | prep = cv4p0784 | collvol = 4 | collvolpages = 784 | year = 1963}}
2. ^{{cite journal| author = W. B. McCormack | title = 3-Methyl-1-Phenylphospholene oxide| volume=43|doi=10.15227/orgsyn.043.0073 |year=1963|journal=Org. Synth.|page=73}}

1 : Phosphines

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