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Saving copy of the {{chembox}} taken from revid 463667630 of page 2,4-Dichlorophenol for the Chem/Drugbox validation project (updated: '').
 
Added bibcode. | Use this tool. Report bugs. | #UCB_Gadget
 
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{{cs1 config|name-list-style=vanc}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid [{{fullurl:2,4-Dichlorophenol|oldid=463667630}} 463667630] of page [[2,4-Dichlorophenol]] with values updated to verified values.}}
{{chembox
{{chembox
| Watchedfields = changed
| verifiedrevid = 443343085
| verifiedrevid = 477211152
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageFileL1 = 2,4-Dichlorophenol.png
| ImageFileL1 = 2,4-Dichlorophenol.png
| ImageSizeL1 = 95px
| ImageNameL1 = Skeletal formula
| ImageNameL1 = Skeletal formula
| ImageFileR1 = 2,4-Dichlorophenol-3D-balls-B.png
| ImageFileR1 = 2,4-Dichlorophenol-3D-balls-B.png
| ImageSizeR1 = 110px
| ImageNameR1 = Ball-and-stick model
| ImageNameR1 = Ball-and-stick model
|IUPACName=2,4-Dichlorophenol
| PIN = 2,4-Dichlorophenol
|OtherNames=
| OtherNames =
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C02625
| KEGG = C02625
| InChI = 1/C6H4Cl2O/c7-4-1-2-6(9)5(8)3-4/h1-3,9H
| InChI = 1/C6H4Cl2O/c7-4-1-2-6(9)5(8)3-4/h1-3,9H
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| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1143
| ChEMBL = 1143
| EINECS = 204-429-6
| Gmelin = 261170
| Beilstein = 742467
| RTECS = SK8575000
| UNNumber = 2020
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H4Cl2O/c7-4-1-2-6(9)5(8)3-4/h1-3,9H
| StdInChI = 1S/C6H4Cl2O/c7-4-1-2-6(9)5(8)3-4/h1-3,9H
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| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=120-83-2
| CASNo=120-83-2
| PubChem=8449
| PubChem=8449
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8140
| ChemSpiderID = 8140
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 16738
| ChEBI = 16738
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII_Ref = {{fdacite|correct|FDA}}
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}}
}}
|Section2={{Chembox Properties
|Section2={{Chembox Properties
| C=6|H=4|O=1|Cl=2
| Formula=C<sub>6</sub>H<sub>4</sub>Cl<sub>2</sub>O
| MolarMass=163.00 g/mol
| MolarMass=
| MolarMass_notes =
| MolarMass_notes =
| Appearance=White/off-white crystalline solid
| Appearance=White solid
| Odour=Phenolic
| Odor=Phenolic
| Density=1.38g/cm<sup>3</sup>
| Density=1.38 g/cm<sup>3</sup>
| MeltingPtC=43.2
| MeltingPtCL=42
| MeltingPt_ref=<ref name=crc>Haynes, p. 3.166</ref>
| MeltingPtCH=43
| BoilingPtC=210
| BoilingPtCL=209
| BoilingPt_ref=<ref name=crc>Haynes, p. 3.166</ref>
| BoilingPtCH=210
| Solubility=5 g/100mL
| Solubility=50 g/L
}}
| SublimationConditions=
|Section4={{Chembox Thermochemistry
| Solubility=
| Thermochemistry_ref=<ref>Haynes, p. 5.12</ref>
| SolubilityProduct=
| DeltaHf = −226.4 kJ·mol<sup>−1</sup> (s)<br> −156.3 kJ·mol<sup>−1</sup> (gas)
| SolubilityProductAs=
| DeltaHc =
| SolubilityOther=
| Solvent=
| Entropy =
| HeatCapacity =
| pKa=
}}
| pKb=
|Section8={{Chembox Hazards
| IsoElectricPt=
| ExternalSDS = [http://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do External MSDS]
| LambdaMax=
| Absorbance=
| MainHazards=
| BandGap=
| NFPA-H = 0
| NFPA-F = 1
| ElectronMobility=
| NFPA-R = 0
| SpecRotation=
| NFPA-S = COR
| MagSus=
| GHSPictograms = {{GHS05}}{{GHS06}}{{GHS07}}{{GHS09}}
| ThermalConductivity=
| GHSSignalWord = Danger
| RefractIndex=
| HPhrases = {{H-phrases|302|311|314|411}}
| Viscosity=
| PPhrases = {{P-phrases|260|264|270|273|280|301+312|301+330+331|302+352|303+361+353|304+340|305+351+338|310|312|321|322|330|361|363|391|405|501}}
| CriticalRelativeHumidity=
| FlashPtC =114
| Dipole=
| FlashPt_ref = <ref>Haynes, p. 16.20</ref>
| AveragePoreSize=
| AutoignitionPtC =
| PoreVolume=
| ExploLimits=
| SpecificSurfaceArea=
| LD50=47.0 mg/kg (oral in rats)<br/>790.0 mg/kg ([[Dermis|Dermal]] exposure in mammals)
}}
| PEL=
|Section3={{Chembox Hazards
| ExternalMSDS= [http://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do External MSDS]
| EUClass =
| MainHazards=
| EUIndex =
| NFPA-H = 4
| NFPA-F = 1
| NFPA-R = 0
| NFPA-O = COR
| RPhrases= {{R22}} {{R24}} {{R34}} {{R51/53}}
| SPhrases= {{S26}} {{S36/37/39}} {{S45}} {{S61}}
| RSPhrases=
| FlashPt=114 °C
| Autoignition=
| ExploLimits=
| LD50=47.0 mg/kg (Oral in rats)<br/>790.0 mg/kg ([[Dermis|Dermal]] exposure in mammals)
| PEL=
}}
}}
}}
}}

'''2,4-Dichlorophenol''' ('''2,4-DCP''') is a [[chlorine|chlorinated]] derivative of [[phenol]] with the molecular formula Cl<sub>2</sub>C<sub>6</sub>H<sub>3</sub>OH. It is a white solid that is mildly acidic (pK<sub>a</sub> = 7.9). It is produced on a large scale as a precursor to the [[herbicide]] [[2,4-dichlorophenoxyacetic acid]] (2,4-D).<ref name=Ull/>

==Production and use==
2,4-DCP is produced by chlorination of phenol.<ref name=Ull>{{Ullmann|author1=François Muller |author2=Liliane Caillard|title=Chlorophenols|year=2011|doi=10.1002/14356007.a07_001.pub2}}</ref>

Annual worldwide production is estimated at 88 million pounds.<ref>Desmurs J, Ratton S. Chlorophenols. In: ''Kirk-Othmer Encyclopedia of Chemical Technology'', 4th Edition. Kroschwitz JI, Howe-Grant M, eds. New York: John Wiley and Sons, 1993;6:156–168</ref> It is also a photo-degradation product of the common [[antibacterial]] and [[Fungicide|antifungal]] agent [[triclosan]] along with the [[Dioxins and dioxin-like compounds|dioxin]] 2,8-dichlorodibenzo-p-dioxin.<ref name="pmid12523412">{{cite journal |vauthors=Singer H, Muller S, Tixier C, Pillonel L |title=Triclosan: occurrence and fate of a widely used biocide in the aquatic environment: field measurements in wastewater treatment plants, surface waters, and lake sediments. |journal=Environ Sci Technol |volume=36 |issue=23 |pages=4998–5004 |year=2002 |pmid=12523412 |doi=10.1021/es025750i|bibcode=2002EnST...36.4998S }}</ref><ref name="pmid15779749">{{cite journal |vauthors=Latch DE, Packer JL, Stender BL, VanOverbeke J, Arnold WA, McNeill K |title=Aqueous photochemistry of triclosan: formation of 2,4-dichlorophenol, 2,8-dichlorodibenzo-p-dioxin, and oligomerization products |journal=Environ. Toxicol. Chem. |volume=24 |issue=3 |pages=517–25 |year=2005 |pmid=15779749|doi=10.1897/04-243R.1|s2cid=19322739 }}</ref>

==Safety==
The [[LD50]] is 580&nbsp;mg/kg (rats, oral). Liquid (molten) 2,4-DCP is readily absorbed through the skin.<ref>{{cite journal |vauthors=Kintz P, Tracqui A, Mangin P |title=Accidental death caused by the absorption of 2,4-dichlorophenol through the skin |journal=Arch. Toxicol. |volume=66 |issue=4 |pages=298–9 |year=1992 |pmid=1514931 |doi= 10.1007/BF02307178|s2cid=23764834 }}</ref> Solid 2,4-DCP does not readily absorb through skin and has a lower NFPA H=3 rating (versus H=4 for molten 2,4-DCP). This is primarily caused by instantaneous [[kidney failure]], [[liver failure]], and failure of various other organs.{{dubious|date=July 2020}}

==See also==
* [[Dichlorophenol]]
* [[2,4-dichlorophenol 6-monooxygenase]]

==References==
{{reflist}}

{{DEFAULTSORT:Dichlorophenol, 2,4-}}
[[Category:Chloroarenes]]
[[Category:Phenols]]
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