Dibenzofuran: Difference between revisions
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{{Chembox |
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{{cleanup|reason = avoid mixing up dibenzofuran with chlorinated derivatives|date=December 2010}} |
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| Watchedfields = changed |
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{{chembox |
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| verifiedrevid = |
| verifiedrevid = 443634542 |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFile = Dibenzofuran-numbering-2D-skeletal.png |
| ImageFile = Dibenzofuran-numbering-2D-skeletal.png |
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| ImageAlt = Skeletal formula showing numbering convention |
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| ImageFile1 = Dibenzofuran |
| ImageFile1 = Dibenzofuran 3D ball.png |
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| ImageAlt1 = Ball-and-stick model of the dibenzofuran molecule |
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| PIN = Dibenzo[''b'',''d'']furan |
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| IUPACName = |
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| OtherNames = |
| OtherNames = |
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|Section1={{Chembox Identifiers |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C07729 |
| KEGG = C07729 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 277497 |
| ChEMBL = 277497 |
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| EC_number = 205-071-3 |
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| UNNumber = 3077 |
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| 3DMet = B01101 |
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| Beilstein = 121100 |
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| Gmelin = 67825 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| 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}} |
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| CASNo = 132-64-9 |
| CASNo = 132-64-9 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 8U54U639VI |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 551 |
| ChemSpiderID = 551 |
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| PubChem = 568 |
| PubChem = 568 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 28145 |
| ChEBI = 28145 |
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| SMILES = o2c1ccccc1c3c2cccc3 |
| SMILES = o2c1ccccc1c3c2cccc3 |
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}} |
}} |
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|Section2={{Chembox Properties |
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| Formula = C<sub>12</sub>H<sub>8</sub>O |
| Formula = C<sub>12</sub>H<sub>8</sub>O |
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| MolarMass = 168.19 g/mol |
| MolarMass = 168.19 g/mol |
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| Appearance = white |
| Appearance = white crystalline powder |
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| Density = |
| Density = |
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| MeltingPtC = 81 to 85 |
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| MeltingPt_notes = |
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| BoilingPt = 285 °C |
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| BoilingPtC = 285 |
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| Solubility = Insoluble |
| Solubility = Insoluble |
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}} |
}} |
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|Section3={{Chembox Hazards |
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| MainHazards = |
| MainHazards = |
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| FlashPt = |
| FlashPt = |
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| AutoignitionPt = |
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| GHSPictograms = {{GHS07}}{{GHS09}} |
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| GHSSignalWord = Warning |
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| SPhrases = {{S24/25}} {{S29}} {{S61}} |
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| HPhrases = {{H-phrases|302|312|332|411}} |
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| PPhrases = {{P-phrases|273|391|501}} |
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}} |
}} |
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|Section4={{Chembox Related |
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| OtherCompounds = [[Furan]]<br />[[Benzofuran]]<br />[[Dibenzodioxin]]<br />[[Dibenzothiophene]]<br />[[Carbazole]]<br />[[Polyozellin]] (compound with a ''kernel'' with two dibenzofurans that share the same benzene ring) |
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'''Dibenzofuran''' |
'''Dibenzofuran''' is a [[heterocyclic]] [[organic compound]] with the [[chemical structure]] shown at right. It is an [[aromatic compound]] that has two [[benzene]] rings fused to a central [[furan]] ring. All the numbered [[carbon]] atoms have a [[hydrogen]] atom bonded to each of them. It is a volatile white solid that is soluble in nonpolar organic solvents. It is obtained from [[coal tar]], 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> |
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== |
==Reactions== |
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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/> |
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'''Dibenzofurans''' can also refer to [[polychlorinated dibenzofurans]] (PCDFs), a family of organic compounds which are [[polyhalogenated compound]]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 [[chlorine]] atoms substituted for each of the hydrogens on the number 2, 3, 7, and 8 carbons (see structure below). Polychlorinated dibenzofurans are very [[toxicity|toxic]] chemicals with properties and chemical structures similar to [[polychlorinated dibenzodioxins]], often simply called [[Dioxins and dioxin-like compounds|dioxin]]. |
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It undergoes electrophilic reactions, such as halogenation and [[Friedel-Crafts]] reactions. Reaction of DBF with butyl lithium results in di[[lithiation]].<ref>Ulrich Iserloh, Yoji Oderaotoshi, Shuji Kanemasa, and [[Dennis Patrick Curran|Dennis P. Curran]] "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> |
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[[Image:2,3,7,8-Tetrachlorodibenzofuran.png|frame|left|Chemical structure of TCDF (2,3,7,8-tetrachlorodibenzofuran)]] |
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Dibenzofuran is the precursor to the drug furobufen by [[Friedel-Crafts]] reaction with [[succinic anhydride]]. |
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The dibenzofuran TCDF (2,3,7,8-tetrachlorodibenzofuran) is the dibenzofuran analog of the [[polychlorinated dibenzodioxins|polychlorinated dibenzodioxin]] TCDD ([[2,3,7,8-tetrachlorodibenzodioxin]]), the poison released in the [[Seveso disaster]]. |
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==Safety== |
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==Environmental and health consequences== |
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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 [[polychlorinated dibenzofurans]] are however among the potentially toxic [[dioxins and dioxin-like compounds]]. |
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⚫ | 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 [[Agency for Toxic Substances and Disease Registry]] (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> |
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'''Probable places of origin''' |
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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. |
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==See also== |
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'''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, [[Agency for Toxic Substances and Disease Registry]], 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> |
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* [[Benzofuran]] |
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'''Pathways of exposure''' |
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{{Reflist}} |
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''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> |
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''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> |
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'''Excretion''': |
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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> |
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'''Regulatory Status''': |
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⚫ | 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 [[Agency for Toxic Substances and Disease Registry]] (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. |
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'''Testing process''' |
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No medical test exists to identify dibenzofuran.<ref>New Jersey Department of Health and Senior Services. Hazardous Substance |
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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> |
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{{reflist}} |
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{{Aryl hydrocarbon receptor modulators}} |
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[[de:Dibenzofuran]] |
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[[es:Dibenzofurano]] |
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[[fr:Dibenzofurane]] |
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[[it:Dibenzofurano]] |
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[[ja:ジベンゾフラン]] |
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[[pl:Dibenzofuran]] |
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[[pt:Dibenzofurano]] |