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Revision as of 17:18, 13 February 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (changes to watched fields - updated 'UNII_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report errors or [[user talk:← Previous edit Latest revision as of 03:13, 7 April 2024 edit undoBernanke's Crossbow (talk | contribs)Extended confirmed users7,846 edits →top: Details 
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{{chembox {{chembox
| Watchedfields = changed |Watchedfields = changed
| verifiedrevid = 396340399 |verifiedrevid = 413715098
|ImageFile=Dichlorophenylphosphine.png |ImageFile1=Dichlorophenylphosphine-2D-by-AHRLS-2012.png
|ImageSize=150px |ImageSize1=150px
|ImageFile2=Dichlorophenylphosphine-3D-balls-by-AHRLS-2012.png
|ImageName=Structural formula
|ImageSize2=150px
|ImageFile1=Phenyldichlorophosphine-3D-balls.png
|ImageSize1=200px
|ImageName1=Ball-and-stick model
|PIN=Phenylphosphonous dichloride |PIN=Phenylphosphonous dichloride
|OtherNames=Dichlorophenylphosphane<br>Phenylphosphorus dichloride |OtherNames=Dichlorophenylphosphane<br>Phenylphosphorus dichloride
|Section1={{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 12053 |ChemSpiderID = 12053
|EC_number = 211-425-8
⚫ | InChI = 1/C6H5Cl2P/c7-9(8)6-4-2-1-3-5-6/h1-5H
|UNNumber = 2798
⚫ | InChIKey = IMDXZWRLUZPMDH-UHFFFAOYAO
|ChEMBL = 1899635
⚫ | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H5Cl2P/c7-9(8)6-4-2-1-3-5-6/h1-5H |InChI = 1/C6H5Cl2P/c7-9(8)6-4-2-1-3-5-6/h1-5H
⚫ |InChIKey = IMDXZWRLUZPMDH-UHFFFAOYAO
⚫ | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫ |StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫ | StdInChIKey = IMDXZWRLUZPMDH-UHFFFAOYSA-N
⚫ |StdInChI = 1S/C6H5Cl2P/c7-9(8)6-4-2-1-3-5-6/h1-5H
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
⚫ |StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫ | CASNo=644-97-3
⚫ |StdInChIKey = IMDXZWRLUZPMDH-UHFFFAOYSA-N
| PubChem=12573
⚫ |CASNo_Ref = {{cascite|correct|CAS}}
⚫ | SMILES = ClP(Cl)c1ccccc1
⚫ |CASNo=644-97-3
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = WRU258L1EW
|PubChem = 12573
|RTECS = TB2478000
⚫ |SMILES = ClP(Cl)c1ccccc1
}} }}
|Section2={{Chembox Properties |Section2={{Chembox Properties
| C = 6 | H = 5 | Cl = 2 | P = 1 |C=6 | H=5 | Cl=2 | P=1
| Appearance= |Appearance= colorless liquid
|Odor = acrid, pungent
| Density=1.3190 g/mL |Density=1.3190 g/mL
| MeltingPt=
|MeltingPtC= -51
| BoilingPt=
|BoilingPtC= 222
| Solubility= |Solubility= insoluble
⚫ }}
|SolubleOther = miscible in ], ], ]
|RefractIndex = 1.6030
⚫ }}
|Section3={{Chembox Hazards |Section3={{Chembox Hazards
| ExternalMSDS = |ExternalSDS =
| NFPA-H = 3 | NFPA-F | NFPA-R = 0 |NFPA-H = 3 | NFPA-F = 1 | NFPA-R = 3 | NFPA-S = W
|GHSPictograms = {{GHS05}}{{GHS06}}{{GHS07}}
| EUClass = Corrosive (C)
|GHSSignalWord = Danger
| FlashPt=
|HPhrases = {{H-phrases|290|301|302|314|335}}
| Autoignition=
|PPhrases = {{P-phrases|234|260|261|264|270|271|280|301+310|301+312|301+330+331|303+361+353|304+340|305+351+338|310|312|321|330|363|390|403+233|404|405|501}}
⚫ }}
|FlashPtC = 101
|AutoignitionPtC = 159
|LD50 = 200 mg/kg (oral, rat)
⚫ }}
}} }}


'''Dichlorophenylphosphine''' is an ] with the ] C<sub>6</sub>H<sub>5</sub>PCl<sub>2</sub>. This colourless viscous liquid is commonly used in the synthesis of ] ligands. '''Dichlorophenylphosphine''' is an ] with the ] C<sub>6</sub>H<sub>5</sub>PCl<sub>2</sub>. This colourless viscous liquid is commonly used in the synthesis of ]s.


Dichlorophenylphosphine is commercially available. It may be prepared by a ] of ] by ], catalyzed by ].<ref>{{OrgSynth | author = B. Buchner and L. B. Lockhart, Jr. | title = Phenyldichlorophosphine | prep = cv4p0784 | collvol = 4 | collvolpages = 784 | year = 1963}}</ref> The compound is an intermediate for the synthesis of other chemicals for instance ]: Dichlorophenylphosphine is commercially available. It may be prepared by an ] of ] by ], catalyzed by ].<ref>{{cite journal | author1 = B. Buchner |author2=L. B. Lockhart, Jr. | title = Phenyldichlorophosphine | journal = Organic Syntheses | doi = 10.15227/orgsyn.031.0088 | volume = 31 | page = 88 | year = 1951}}</ref><ref name=ECSynth>{{cite book|title=Synthesis of Carbon–Phosphorus Bonds|year=2004|edition=2|first1=Robert |last1=Engel |first2=Jaime-Lee Iolani |last2=Cohen|publisher= CRC|isbn=0-8493-1617-0|at=&sect;6.2.3}}</ref> However, ] often induces diarylation; a cleaner catalyst for monoarylation is ].<ref name=ECSynth/> The compound is an intermediate for the synthesis of other chemicals for instance ]:
:C<sub>6</sub>H<sub>5</sub>PCl<sub>2</sub> + 2 CH<sub>3</sub>MgI → C<sub>6</sub>H<sub>5</sub>P(CH<sub>3</sub>)<sub>2</sub> + 2 MgICl :C<sub>6</sub>H<sub>5</sub>PCl<sub>2</sub> + 2 CH<sub>3</sub>MgI → C<sub>6</sub>H<sub>5</sub>P(CH<sub>3</sub>)<sub>2</sub> + 2 MgICl
Many tertiary phosphines can be prepared by this route.<ref>{{cite journal |doi=10.15227/orgsyn.055.0127|title=Sulfide Contraction via Alkylative Coupling: 3-Methyl-2,4-heptanedione |journal=Organic Syntheses |year=1976 |volume=55 |page=127|author=P. Loeliger E. Flückiger }}</ref>


In the ] dichlorophenylphosphine adds ]s to give the ] ring.<ref>{{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}}</ref>
Dichlorophenylphosphine undergoes the ] upon treatment with ]s to give ]s.
:]

Reductive coupling of the dichlorophosphine gives the ] (PhP)<sub>5</sub>.<ref>{{cite journal | author = Marianne Baudler, Klaus Glinka | title = Monocyclic and Polycyclic Phosphines | journal = ] | year = 1993 | volume = 93 | pages = 1623–1667 | doi = 10.1021/cr00020a010}}</ref>


==References== ==References==
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