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Revision as of 16:28, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 457963284 of page 1,4-Dichlorobenzene for the Chem/Drugbox validation project (updated: 'ChemSpiderID', 'ChEMBL').		Latest revision as of 21:29, 10 February 2024 edit Michael7604 (talk | contribs)Extended confirmed users8,895 edits is an aryl chloride and
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			{{Use dmy dates|date=December 2019}}
	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
	{{chembox		{{chembox
	| Verifiedfields = changed		|Verifiedfields = changed
			|Watchedfields = changed
	| verifiedrevid = 456365616
			|verifiedrevid = 477206149
	| Name = 1,4-Dichlorobenzene
	| ImageFileL1 = 1,4-dichlorobenzene.svg		|Name = 1,4-Dichlorobenzene
			|ImageFileL1 = 1,4-dichlorobenzene.svg
	| ImageSizeL1 = 80px		|ImageSizeL1 = 70px
	| ImageNameL1 = 1,4-Dichlorobenzene		|ImageNameL1 = 1,4-Dichlorobenzene
	| ImageFileR1 = Para-dichlorobenzene-3D-balls.png		|ImageFileR1 = P-Dichlorobenzene-3D-balls.png
			|ImageNameR1 = Ball-and-stick model of 1,4-dichlorobenzene
	| ImageSizeR1 = 100px
	| ImageNameR1 = Ball-and-stick model of 1,4-dichlorobenzene		| ImageFile2=1,4 dichlorobenzene crystallised.jpg
			|ImageCaption2 = 1,4-dichlorobenzene crystallised on paper from ] solution
	| IUPACName = 1,4-Dichlorobenzene
	| OtherNames = ''para''-Dichlorobenzene<br />''p''-Dichlorobenzene<br />p-DCB<br/>PDB<br/>Paramoth<br/>Para crystals<br/>Paracide <br>Moth Nuggets</br>		|PIN = 1,4-Dichlorobenzene
			|OtherNames = 1,4-DCB<br />''para''-Dichlorobenzene<br />''p''-Dichlorobenzene<br />p-DCB<br />PDCB<br/>Paramoth<br />Para crystals<br />Paracide<br />Dichlorocide
	| Section1 = {{Chembox Identifiers		|Section1 = {{Chembox Identifiers
	| SMILES = ClC1=CC=C(Cl)C=C1		|SMILES = ClC1=CC=C(Cl)C=C1
	| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}		|StdInChI_Ref = {{stdinchicite|changed|chemspider}}
			|StdInChI = 1S/C6H4Cl2/c7-5-1-2-6(8)4-3-5/h1-4H
	| ChemSpiderID = 4523
	| ChEMBL_Ref = {{ebicite|changed|EBI}}		|StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
			|StdInChIKey = OCJBOOLMMGQPQU-UHFFFAOYSA-N
	| ChEMBL = <!-- blanked - oldvalue: 190982 -->
			|ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
	| UNII_Ref = {{fdacite|correct|FDA}}
			|ChemSpiderID = 13866817
	| UNII = D149TYB5MK
			|PubChem = 4685
	| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 106-46-7		|EC_number = 203-400-5
			|UNNumber = 3077
	| RTECS = CZ4550000
	| KEGG_Ref = {{keggcite|correct|kegg}}		|ChEBI_Ref = {{ebicite|correct|EBI}}
	| KEGG = C07092		|ChEBI = 28618
			|ChEMBL_Ref = {{ebicite|correct|EBI}}
	}}
			|ChEMBL = 190982
	| Section2 = {{Chembox Properties
			|UNII_Ref = {{fdacite|correct|FDA}}
	| C=6|H=4|Cl=2
			|UNII = D149TYB5MK
	| Density = 1.25&nbsp;g/cm³, solid
			|CASNo_Ref = {{cascite|correct|CAS}}
	| Solubility = 10.5&nbsp;mg/100&nbsp;mL (20&nbsp;°C)
			|CASNo = 106-46-7
	| MeltingPtC = 53.5
			|RTECS = CZ4550000
	| BoilingPtC = 174
			|KEGG_Ref = {{keggcite|correct|kegg}}
	}}
			|KEGG = C07092
	| Section7 = {{Chembox Hazards
			|Beilstein = 1680023
	| EUClass = {{Hazchem Xn}}<br />{{Hazchem N}}<br />]
	| NFPA-H = 2		|Gmelin = 49722
	| NFPA-F = 2
	| NFPA-R =
	| RPhrases = {{R36}} {{R40}} {{R50/53}}
	| SPhrases = {{S2}} {{S36/37}} {{S46}} {{S60}} {{S61}}
	| FlashPt = 66&nbsp;°C
	}}
	| Section8 = {{Chembox Related
	| OtherCpds = ]<br />]
	}}
	}}		}}
			|Section2 = {{Chembox Properties
			|C=6 | H=4 | Cl=2
			|Density = 1.25&nbsp;g/cm<sup>3</sup>, solid
			|Solubility = 10.5&nbsp;mg/100&nbsp;mL (20&nbsp;°C)
			|MeltingPtC = 53.5
			|BoilingPtC = 174
			|Appearance = Colorless/white crystals<ref name=PGCH/>
			|Odor = mothball-like<ref name=PGCH/>
			|VaporPressure = 1.3 mmHg (20&nbsp;°C)<ref name=PGCH/>
			|MagSus = -82.93·10<sup>−6</sup> cm<sup>3</sup>/mol
			}}
			|Section3 = {{Chembox Hazards
			|MainHazards = Suspected ]
			|NFPA-H = 2
			|NFPA-F = 2
			|NFPA-R = 0
			|GHSPictograms = {{GHS07}}{{GHS08}}{{GHS09}}
			|GHSSignalWord = Warning
			|HPhrases = {{H-phrases|302|315|317|319|332|335|351|410}}
			|PPhrases = {{P-phrases|201|202|261|264|270|271|272|273|280|281|301+312|302+352|304+312|304+340|305+351+338|308+313|312|321|330|332+313|333+313|337+313|362|363|391|403+233|405|501}}
			|FlashPtC = 66
			|PEL = TWA 75 ppm (450 mg/m<sup>3</sup>)<ref name=PGCH>{{PGCH|0190}}</ref>
			|ExploLimits = 2.5%-?<ref name=PGCH/>
			|IDLH = Ca <ref name=PGCH/>
			|REL = Ca<ref name=PGCH/>
			|LD50 = 500 mg/kg (rat, oral)<br/>2950 mg/kg (mouse, oral)<br/>2512 mg/kg (rat, oral)<br/>2830 mg/kg (rabbit, oral)<ref name=IDLH>{{cite web |url = https://www.cdc.gov/niosh/idlh/106467.html |title = ''p''-Dichlorobenzene |publisher = National Institute for Occupational Safety and Health (NIOSH) |date = 4 December 2014 |access-date = 6 March 2015}}</ref>
			|LDLo = 857 mg/kg (human, oral)<br/>4000 mg/kg (rat, oral)<br/>2800 mg/kg (guinea pig, oral)<ref name=IDLH/>
			}}
			|Section4 = {{Chembox Related
			|OtherCompounds = ]<br />]
			}}
			}}
			'''1,4-Dichlorobenzene''' ('''1,4-DCB''', '''''p'''''-'''DCB''', or '''''para'''''-'''dichlorobenzene''', sometimes abbreviated as '''PDCB''' or '''para''') is an ] and isomer of ] with the ] C<sub>6</sub>H<sub>4</sub>Cl<sub>2</sub>. This colorless solid has a strong ]. The molecule consists of a ] ring with two ] atoms (replacing hydrogen atoms) on opposing sites of the ring.
			It is used as a ], ], and ], most familiarly in ]s in which it is a replacement for the more traditional ] because of naphthalene's greater ] (though both chemicals have the same ]). It is also used as a ] in the production of the chemically and thermally resistant polymer ].<ref name=Ross>{{Ullmann | last1 = Rossberg | first1 = M. | last2 = Lendle | first2 = W. | last3 = Pfleiderer | first3 = G. | last4 = Tögel | first4 = A. | last5 = Dreher | first5 = E. L. | last6 = Langer | first6 = E. | last7 = Rassaerts | first7 = H. | last8 = Kleinschmidt | first8 = P. | last9 = Strack | first9 = H. | last10 = Cook | first10 = R. | last11 = Beck | first11 = U. | last12 = Lipper | first12 = K.-A. | last13 = Torkelson | first13 = T.R.| last14 = Löser | first14 = E. | last15 = Beutel | first15 = K.K. | last16 = Mann | first16 = T. | title= Chlorinated Hydrocarbons| year = 2006 | doi=10.1002/14356007.a06_233.pub2}}</ref>
			== Production ==
			''p''-DCB is produced by ] of benzene using ] as a catalyst:
			:C<sub>6</sub>H<sub>6</sub> + 2 Cl<sub>2</sub> → C<sub>6</sub>H<sub>4</sub>Cl<sub>2</sub> + 2 ]
			The chief impurity is the 1,2 ]. The compound can be purified by ], taking advantage of its relatively high ] of 53.5&nbsp;°C; the isomeric ]s and ] melt well below room temperature.<ref name=Ross/>
			== Uses ==
			=== Disinfectant, deodorant, and pesticide===
			] disinfectant]]
			''p''-DCB is used to control ]s, ]s, and ].<ref name="orst">{{cite web |url= http://npic.orst.edu/capro/Mothballs1.pdf |title= National Pesticide Information Center – Mothballs Case Profile |access-date= 10 August 2009 |archive-url= https://web.archive.org/web/20100622021329/http://npic.orst.edu/capro/Mothballs1.pdf |archive-date= 22 June 2010 |df= dmy-all}}</ref> It also finds use as a disinfectant<ref name=Ross/> in waste containers and restrooms and is the characteristic smell associated with ]s. Its usefulness for these applications arises from ''p''-DCB's low ] in water and its relatively high ]: it ] readily near room temperature.<ref name=Ross/>
			=== Precursor to other chemicals ===
			] gives ], a precursor to commercial ]s and pigments.<ref name=Ullmann1>K. Hunger. W. Herbst "Pigments, Organic" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim, 2012. {{doi|10.1002/14356007.a20_371}}</ref> The chloride sites on ''p''-DCB can be ] with hydroxylamine and sulfide groups. In a growing application, ''p''-DCB is the precursor to the high performance polymer poly(''p''-phenylene sulfide):<ref>{{Cite journal | last1 = Fahey | first1 = D. R. | last2 = Ash | first2 = C. E. | doi = 10.1021/ma00015a003 | title = Mechanism of poly(''p''-phenylene sulfide) growth from ''p''-dichlorobenzene and sodium sulfide | journal = Macromolecules | volume = 24 | issue = 15 | page = 4242 | year = 1991 | bibcode = 1991MaMol..24.4242F }}</ref>
			:]
			== Environmental and health effects ==
			''p''-DCB is poorly soluble in water and is not easily broken down by ]. Like many ]s, ''p''-DCB is ] and will accumulate in fatty tissues if consumed by a person or animal.
			The United States ] (DHHS) and the ] (IARC) have determined that ''p''-DCB may reasonably be anticipated to be a ].<ref> {{Webarchive|url=https://web.archive.org/web/20160809225810/http://monographs.iarc.fr/ENG/Preamble/currentb6evalrationale0706.php |date=9 August 2016 }} definition of "Group 2B: Possibly carcinogenic to humans", the ] classification of this chemical</ref> This has been indicated by animal studies, although a full-scale human study has not been done.<ref name=ToxFAQ-Dichlor>{{cite web|title=ToxFAQs for Dichlorobenzenes|url=https://wwwn.cdc.gov/TSP/ToxFAQs/ToxFAQsLanding.aspx?id=703&tid=126|work=Toxic Substances Portal|publisher=Agency for Toxic Substances and Disease Registry|access-date=24 May 2013}}</ref>
			The ] (EPA) has set a target maximum ] of 75 ] of ''p''-DCB per liter of ] (75&nbsp;μg/L),<ref name="epa-water">{{cite web |url= http://www.epa.gov/ogwdw000/contaminants/dw_contamfs/p-dichlo.html |title= Consumer Factsheet on: PARA-DICHLOROBENZENE (p-DCB) |date= 28 November 2006 |access-date=10 August 2009 | archive-url= https://web.archive.org/web/20091006081817/http://www.epa.gov/ogwdw000/contaminants/dw_contamfs/p-dichlo.html| archive-date= 6 October 2009 <!--Added by DASHBot-->}}</ref> but publishes no information on the cancer risk.<ref>{{Cite web|url=https://www3.epa.gov/airtoxics/hlthef/dich-ben.html|title=1,4-Dichlorobenzene (para-Dichlorobenzene) |website=US Environmental Protection Agency |language=en|access-date=24 March 2016|archive-date=4 April 2016|archive-url=https://web.archive.org/web/20160404214242/https://www3.epa.gov/airtoxics/hlthef/dich-ben.html}}</ref> ''p''-DCB is also an ]-registered ].<ref name="epa-rereg">{{cite web |url= http://www.epa.gov/oppsrrd1/REDs/para-dichlorobenzene-red-revised.pdf |title= Reregistration Eligibility Decision for Para-dichlorobenzene |date= December 2008 |access-date=10 August 2009 | archive-url= https://web.archive.org/web/20090926200251/http://www.epa.gov/oppsrrd1/REDs/para-dichlorobenzene-red-revised.pdf| archive-date= 26 September 2009 <!--Added by DASHBot-->}}</ref> The United States ] (OSHA) has set a maximum level of 75 parts of ''p''-DCB per million parts air in the workplace (75&nbsp;ppm) for an 8-hour day, 40-hour ].<ref>{{Cite web|url=https://www.osha.gov/dts/chemicalsampling/data/CH_232900.html|title=Chemical Sampling – p-Diclorobenzine|website=United States Department of Labor|publisher=Occupational Safety & Health Administration|access-date=23 March 2016|archive-date=31 July 2017|archive-url=https://web.archive.org/web/20170731224645/https://www.osha.gov/dts/chemicalsampling/data/CH_232900.html}}</ref><ref>{{Cite web|url=http://nj.gov/health/eoh/rtkweb/documents/fs/0643.pdf|title=Common Name: 1,4-DICHLOROBENZENE|date=December 2005|publisher=New Jersey Department of Health and Senior Services|access-date=24 March 2016}}</ref>
			A mechanism for the carcinogenic effects of mothballs and some types of air fresheners containing ''p''-DCB has been identified in roundworms.<ref name="EHANS">{{cite journal|title=The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans|last=Kokel|first=David|date=14 May 2006|volume=2|issue=6|doi=10.1038/nchembio791|pmid=16699520|pages=338–345|journal=Nature Chemical Biology|s2cid=18402091 }}</ref>
			Due to its carcinogenic nature, use of paradichlorobenzene in the European Union is forbidden as an air freshener (since 2005) and in mothballs (since 2008).
			=== Biodegradation ===
			'']'' is a ] species able to degrade dichlorobenzene as its sole ] source.<ref>{{Cite journal | last1 = Rehfuss | first1 = M. | last2 = Urban | first2 = J. | doi = 10.1016/j.syapm.2005.05.011 | title = ''Rhodococcus phenolicus'' sp. nov., a novel bioprocessor isolated actinomycete with the ability to degrade chlorobenzene, dichlorobenzene and phenol as sole carbon sources | journal = Systematic and Applied Microbiology | volume = 28 | issue = 8 | pages = 695–701 | year = 2005 | pmid = 16261859}}</ref>
			== See also ==
			* ]
			* ]
			* ]
			== References ==
			{{reflist}}
			== External links ==
			* {{ICSC|0037|00}}
			* , ''BBC News'', 27 July 2006
			* , Centers for Disease Control and Prevention
			{{DEFAULTSORT:Dichlorobenzene, 1, 4-}}
			]
			]
			]