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			{{Chembox
	{{cleanup|reason = avoid mixing up dibenzofuran with chlorinated derivatives|date=December 2010}}
			| Watchedfields = changed
	{{chembox
	| verifiedrevid = 414417988		| verifiedrevid = 443634542
	| ImageFile_Ref = {{chemboximage|correct|??}}		| ImageFile_Ref = {{chemboximage|correct|??}}
	| ImageFile = Dibenzofuran-numbering-2D-skeletal.png		| ImageFile = Dibenzofuran-numbering-2D-skeletal.png
	| ImageName = Skeletal formulashowing numbering convention		| ImageAlt = Skeletal formula showing numbering convention
	| ImageFile1 = Dibenzofuran-3D-balls.png		| ImageFile1 = Dibenzofuran 3D ball.png
	| ImageName1 = Ball-and-stick model		| ImageAlt1 = Ball-and-stick model of the dibenzofuran molecule
			| PIN = Dibenzofuran
	| IUPACName =
	| OtherNames =		| OtherNames =
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| KEGG_Ref = {{keggcite|correct|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = C07729		| KEGG = C07729
Line 16:		Line 16:
	| ChEMBL_Ref = {{ebicite|correct|EBI}}		| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 277497		| ChEMBL = 277497
			| EC_number = 205-071-3
			| UNNumber = 3077
			| 3DMet = B01101
			| Beilstein = 121100
			| Gmelin = 67825
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C12H8O/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8H		| StdInChI = 1S/C12H8O/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8H
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	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 132-64-9		| CASNo = 132-64-9
			| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = 8U54U639VI
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 551		| ChemSpiderID = 551
	| PubChem = 568		| PubChem = 568
			| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 28145		| ChEBI = 28145
	| SMILES = o2c1ccccc1c3c2cccc3		| SMILES = o2c1ccccc1c3c2cccc3
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| Formula = C<sub>12</sub>H<sub>8</sub>O		| Formula = C<sub>12</sub>H<sub>8</sub>O
	| MolarMass = 168.19 g/mol		| MolarMass = 168.19 g/mol
	| Appearance = white to pale yellow crystalline powder		| Appearance = white crystalline powder
	| Density =		| Density =
	| MeltingPt = 81 - 85 °C		| MeltingPtC = 81 to 85
			| MeltingPt_notes =
	| BoilingPt = 285 °C
			| BoilingPtC = 285
	| Solubility = Insoluble		| Solubility = Insoluble
	}}		}}
	| Section3 = {{Chembox Hazards		|Section3={{Chembox Hazards
	| MainHazards =		| MainHazards =
	| FlashPt =		| FlashPt =
	| Autoignition =		| AutoignitionPt =
	| RPhrases = {{R51/53}}		| GHSPictograms = {{GHS07}}{{GHS09}}
			| GHSSignalWord = Warning
	| SPhrases = {{S24/25}} {{S29}} {{S61}}
			| HPhrases = {{H-phrases|302|312|332|411}}
			| PPhrases = {{P-phrases|273|391|501}}
	}}		}}
	| Section4 = {{Chembox Related		|Section4={{Chembox Related
	| OtherCpds = ]<br />]<br />]<br />]<br />]<br />] (compound with a ''kernel'' with two dibenzofurans that share the same benzene ring)		| OtherCompounds = ]<br />]<br />]<br />]<br />]<br />] (compound with a ''kernel'' with two dibenzofurans that share the same benzene ring)
	}}		}}
	}}		}}
	'''Dibenzofuran''', is a ] ] with the ] shown at right. It is an ] that has two ] rings fused to one ] ring in the middle. All of the numbered ] atoms have a ] atom bonded to each of them (not shown in the image). Dibenzofuran is an ] ] having the chemical formula C<sub>12</sub>H<sub>8</sub>O.		'''Dibenzofuran''' is a ] ] with the ] shown at right. It is an ] that has two ] rings fused to a central ] ring. All the numbered ] atoms have a ] atom bonded to each of them. It is a volatile white solid that is soluble in nonpolar organic solvents. It is obtained from ], where it exists as a 1% component.<ref name=Ullmann>Gerd Collin and Hartmut Höke "Benzofurans" in Ullmann's Encyclopedia of Industrial Chemistry, 2007, Wiley-VCH, Weinheim. {{doi|10.1002/14356007.l03_l01}}</ref>
	==Dibenzofurans==		==Reactions==
			Dibenzofuran is thermally robust with a convenient liquid range. These properties, together with its low toxicity, are exploited by the use of DBF as a heat transfer agent.<ref name=Ullmann/>
	'''Dibenzofurans''' can also refer to ] (PCDFs), a family of organic compounds which are ]s which have atom or group substitutions made for the hydrogens on any of the numbered carbon atoms in the dibenzofuran structure. For example, 2,3,7,8-tetrachlorodibenzofuran (TCDF) has ] atoms substituted for each of the hydrogens on the number 2, 3, 7, and 8 carbons (see structure below). Polychlorinated dibenzofurans are very ] chemicals with properties and chemical structures similar to ], often simply called ].
			It undergoes electrophilic reactions, such as halogenation and ] reactions. Reaction of DBF with butyl lithium results in di].<ref>Ulrich Iserloh, Yoji Oderaotoshi, Shuji Kanemasa, and ] "Synthesis of (R,R)-4,6-Dibenzofurandiyl-2,2'-Bis (4-Phenyloxazoline) (DBFOX/PH) – A Novel Trridentate Ligand" Org. Synth. 2003, volume 80, 46. {{doi|10.15227/orgsyn.080.0046}}</ref>
	]
			Dibenzofuran is the precursor to the drug furobufen by ] reaction with ].
	The dibenzofuran TCDF (2,3,7,8-tetrachlorodibenzofuran) is the dibenzofuran analog of the ] TCDD (]), the poison released in the ].
			==Safety==
	==Environmental and health consequences==
			Dibenzofuran is a relatively non-toxic compound as evidenced by rats being unaffected after a 200-day diet consisting of 0.025 – 0.4% of DBF.<ref name=Ullmann/> The ] are however among the potentially toxic ].
		⚫	Dibenzofuran is cited in the United States Clean Air Act 1990 Amendments -Hazardous Air Pollutants as a volatile hazardous air pollutant of potential concern. The Superfund Amendment Reauthorization Act (SARA) Section 110 placed dibenzofuran on the revised ] (ATSDR) priority list of hazardous substances to be the subject of a toxicological profile. The listing was based on the substance’s frequency of occurrence at Comprehensive Environmental Response, Compensation, and Liability Act (CERCLA) National Priorities List sites, its toxicity, and/or its potential for human exposure.<ref name=niehs>{{cite web |url=https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/dibenzofuran_508.pdf |title=Archived copy |access-date=2014-03-09 |archive-url=https://web.archive.org/web/20121009105332/http://ntp.niehs.nih.gov/ntp/htdocs/Chem_Background/ExSumPdf/Dibenzofuran.pdf |archive-date=2012-10-09 }}</ref>
	'''Probable places of origin'''
	It is a white crystal-like solid created from production of coal tar.<ref>http://www.epa.gov/epawaste/hazard/wastemin/minimize/factshts/dibenzof.pdf</ref> It is used as an insecticide, in the production of PVC, industrial bleaching and incineration.
			==See also==
	'''Production and Producers''': Dibenzofuran is recovered from a wash oil fraction of coal tar that boils between 275 °C and 290 °C. Redistillation separates dibenzofuran from acenaphthene, which boils at a lower temperature. Crystallization of the redistilled fraction then produces technically pure dibenzofuran.<ref>Elvers, B., Hawkins, S., Ravenscroft, M., Rounsaville, J.F. & Schulz, G., eds. (1989) Ullmann’s Encyclopedia of Industrial Chemistry. 5th ed., vol A12, NY, VCH Publishers, pp130-131</ref> Typical wood preservative creosote is approximately 3.5% dibenzofuran. Dibenzofuran occurs at levels of 0.19-1.50 wt % of dry tar in commercial coal tars.<ref>ATSDR (1990) Toxicological Profile for Creosote (TP-90-09). Atlanta, GA, ], pp 1-4, 9, 63-68</ref> It also is a by-product of smoking and affects both the smoker and second hand smokers.<ref name=niehs>http://ntp.niehs.nih.gov/ntp/htdocs/Chem_Background/ExSumPdf/Dibenzofuran.pdf</ref>
			* ]
		⚫	==References==
	'''Pathways of exposure'''
			{{Reflist}}
	''Occupational exposure'' to dibenzofuran may occur through inhalation and dermal contact, particularly at sites where coal tar, coal tar derivatives, and creosote are produced and used.<ref>U.S. Department of Health and Human Services. Hazardous Substances Data Bank (HSDB, online database).</ref><ref>Polychlorinated dibenzo-p-dioxin and dibenzofuran concentrations in serum samples of workers at intermittently burning municipal waste incinerators in Japan. Occupational and Environmental Medicine 2002;59:362-368</ref>
	''General Population Exposure'': Fish and dairy intake also have been studied to be related with body burden of dibenzofuran in pregnant women.<ref>Associations of diet with body burden of dibenzo-p-dioxins and dibenzofurans (PCDD/Fs) and dioxin-like polychlorinated biphenyls (PCBs): observations on pregnant women from central Taiwan. Food Addit Contam. 2007 Jul;24(7):784-91</ref> Consumption of contaminated water and food are the primary sources of exposure.<ref>Congener-Specific Levels of Dioxins and Dibenzofurans in U.S. Food and Estimated Daily Dioxin Toxic Equivalent Intake. The National Institute of Environmental Health Sciences (NIEHS).</ref>
	'''Excretion''':
	Dibenzofuran is excreted 22% the daily intake of dioxins from meals is excreted from feces and 29% from sebum.<ref>Balance of Intake and Excretion of 20 Congeners of Polychlorinated Dibenzo-p-dioxin, Polychlorinated Dibenzofuran and Coplanar Polychlorinated Biphenyl in Healthy Japanese Men. J Health Sci. VOL.47; NO.2; PAGE.145-154(2001)</ref>
	'''Regulatory Status''':
⚫	Dibenzofuran is cited in the Clean Air Act 1990 Amendments -Hazardous Air Pollutants as a volatile hazardous air pollutant of potential concern. The Superfund Amendment Reauthorization Act (SARA) Section 110 placed dibenzofuran on the revised ] (ATSDR) priority list of hazardous substances to be the subject of a toxicological profile. The listing was based on the substance’s frequency of occurrence at Comprehensive Environmental Response, Compensation, and Liability Act (CERCLA) National Priorities List sites, its toxicity, and/or its potential for human exposure. Dibenzofuran is also listed in the Massachusetts Substance List for Right-to-Know Law, the New Jersey Department of Health Hazard Right-to-Know Program Hazardous Substance List, and the Pennsylvania Department of Labor and Industry Hazardous Substance List. California’s Air Toxics “Hot Spots” List (Assembly Bill).<ref name=niehs/>
	'''Testing process'''
	No medical test exists to identify dibenzofuran.<ref>New Jersey Department of Health and Senior Services. Hazardous Substance
	Fact Sheet: Dibenzofuran - http://nj.gov/health/eoh/rtkweb/documents/fs/2230.pdf</ref> But if symptoms of eye, nose, throat or skin irritation occurs after exposure (accidentally / workplace) medical attention is recommended. EPA uses High Performance Liquid Chromatography (HPLC) to monitor samples.<ref>http://www.osha.gov/dts/chemicalsampling/data/CH_231985.html</ref><ref>Determination of OCDD and OCDF in soils and biological samples by GC/ECD. Waste testing and quality assurance. 3rd Vol. ASTM STP 1075. D.Friedman. American society for testing and materials.</ref>
⚫	==References==
	{{reflist}}
			{{Aryl hydrocarbon receptor modulators}}
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