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Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: StdInChI StdInChIKey.
→‎External links: ChemID now part of PubChem, which is linked in Chembox
 
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{{see also|1,4-Dioxin|Dioxins and dioxin-like compounds|Polychlorinated dibenzodioxins}}
{{chembox
{{chembox
| Watchedfields = changed
| verifiedrevid = 389085567
| verifiedrevid = 396327766
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| Name = Dibenzo-''p''-dioxin
| ImageFile = Dibenzo-p-dioxin.svg
| Name = Dibenzo-''p''-dioxin
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| ImageFile = Dibenzo-p-dioxin.svg
| ImageSize = 200px
| ImageName = Dibenzodioxin
| ImageSize =180px
| ImageName = Dibenzodioxin
| ImageFile1 = Dibenzo-p-dioxin-3D-vdW.png
| ImageFile1 = Dibenzo-1,4-dioxin-3D-balls.png
| ImageSize1 = 160
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| IUPACName = Dibenzo-1,4-dioxin
| ImageAlt1 = Ball-and-stick model
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| OtherNames =Dibenzodioxin, <br>Dibenzo-''p''-dioxin, <br>Oxanthrene
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| ImageFile2 = Dibenzo-1,4-dioxin-3D-spacefill.png
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| Section1 = {{Chembox Identifiers
| ChemSpiderID = 8861
| ImageSize2 = 140
| ImageAlt2 = Space-filling model
| PIN = Oxanthrene<ref>{{cite book |author=[[International Union of Pure and Applied Chemistry]] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=[[Royal Society of Chemistry|The Royal Society of Chemistry]] |pages=216 |doi=10.1039/9781849733069-00130 |isbn=978-0-85404-182-4}}</ref>
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| OtherNames = Dibenzodioxin, <br>Dibenzo-''p''-dioxin, <br>Dibenzo-1,4-dioxin
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|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8861
| InChI = 1/C12H8O2/c1-2-6-10-9(5-1)13-11-7-3-4-8-12(11)14-10/h1-8H
| InChI = 1/C12H8O2/c1-2-6-10-9(5-1)13-11-7-3-4-8-12(11)14-10/h1-8H
| SMILES = O1c3c(Oc2c1cccc2)cccc3
| SMILES = O1c3c(Oc2c1cccc2)cccc3
| InChIKey = NFBOHOGPQUYFRF-UHFFFAOYAJ
| InChIKey = NFBOHOGPQUYFRF-UHFFFAOYAJ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C12H8O2/c1-2-6-10-9(5-1)13-11-7-3-4-8-12(11)14-10/h1-8H
| StdInChI = 1S/C12H8O2/c1-2-6-10-9(5-1)13-11-7-3-4-8-12(11)14-10/h1-8H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = NFBOHOGPQUYFRF-UHFFFAOYSA-N
| StdInChIKey = NFBOHOGPQUYFRF-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 262-12-4
| CASNo = 262-12-4
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C07732
| PubChem = 9216
| EC_number = 205-974-2
| UNNumber = 3077
| UNII = O1B5KJ235I
| ChEBI = 28891
| ChEMBL = 3184198
| Beilstein = 143227
| Gmelin = 280302
}}
}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
| C=12 | H=8 | O=2
| Formula = C<sub>12</sub>H<sub>8</sub>O<sub>2</sub>
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| Appearance = White crystals
| MolarMass = 184.20 g/mol
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| Density =
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| Appearance = White crystals
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| Solubility = 0.901 g/L (25 °C)
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| Density =
| MeltingPtC = 122
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| Solubility in water = 0.901 g/L (25 °C)
| MeltingPtC = 122
| BoilingPtC = 283.5
| Viscosity =
| BoilingPtC = 283.5
| Viscosity =
| Dipole =
| Dipole =
}}
}}
| Section7 = {{Chembox Hazards
|Section7={{Chembox Hazards
| FlashPt =
| FlashPt =
| EUClass =
| NFPA-F =
| NFPA-F =
| NFPA-R =
| GHSPictograms = {{GHS07}}{{GHS09}}
| NFPA-R =
| GHSSignalWord = Warning
| RPhrases =
| HPhrases = {{H-phrases|H302|411}}
| SPhrases =
| PPhrases = {{P-phrases|P264|270|273|301+312|330|391|501}}
}}
}}
| Section8 = {{Chembox Related
|Section8={{Chembox Related
| OtherCpds = [[Polychlorinated dibenzodioxins|dioxin]]<br>[[1,4-dioxin]]<br>[[polychlorinated dibenzodioxins]]}}
| OtherCompounds = [[polychlorinated dibenzodioxins]] ("dioxin"),<br>[[dioxins and dioxin-like compounds]]}}
}}
}}


'''Dibenzo-1,4-dioxin''', also '''dibenzodioxin''' or '''dibenzo-''p''-dioxin''' (dibenzo-''para''-dioxin), is a [[polycyclic compound|polycyclic]] [[heterocyclic compound|heterocyclic]] [[organic chemistry|organic]] compound in which two [[benzene]] rings are connected by a [[1,4-Dioxin|1,4-dioxin]] ring. Its molecular formula is C<sub>12</sub>H<sub>8</sub>O<sub>2</sub>. The two oxygen atoms occupy opposite ([[arene substitution pattern|''para''-]]) positions in the six-membered dioxin ring.
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{{seealso|1,4-Dioxin|Dioxins and dioxin-like compounds|Polychlorinated dibenzodioxins}}


Dibenzodioxin is the [[skeletal formula|carbon skeleton]] of the poisonous [[polychlorinated dibenzodioxins]] (PCDDs), often called dioxins. The most harmful PCDD is [[2,3,7,8-Tetrachlorodibenzodioxin|2,3,7,8-tetrachlorodibenzodioxin]] (TCDD). [[Dioxins and dioxin-like compounds]] is a category of pollutants that includes PCDDs and other compounds that have similar structure, toxicity, and persistence. Dibenzodioxin is also the skeleton of the polybrominated dibenzodioxins.


==Isomer==
'''Dibenzodioxin''', C<sub>12</sub>H<sub>8</sub>O<sub>2</sub>, is an organic [[organic chemistry|heterocyclic]] compound in which two benzene rings are attached to a [[1,4-Dioxin|dioxin]] ring.
The general name '''dibenzodioxin''' usually refers to dibenzo-''p''-dioxin.


[[File:Dibenzo-1,2-dioxin.svg|thumb|left|120px|Dibenzo-''o''-dioxin (dibenzo-1,2-dioxin)]]
[[Image:Dibenzodioxin isomers.png]]
The [[isomer]]ic compound dibenzo-''o''-dioxin (dibenzo-''ortho''-dioxin) or dibenzo-1,2-dioxin, like the unstable [[1,2-Dioxin|1,2-dioxin]], has two adjacent oxygen atoms ([[arene substitution pattern|''ortho''-]]). No detailed information is available on this isomer, but it is expected to be highly unstable, with [[organic peroxide|peroxide]]-like characteristics.{{clear left}}


==See also==
The name generally refers to the '''dibenzo-''p''-dioxin''', as no detailed information is available on the dibenzo-''o''-dioxin isomer, expected to be highly unstable with [[organic peroxide|peroxide]]-like characteristics.
*[[Thianthrene]], the sulfur analog of dibenzodioxin


==References==
Dibenzodioxin forms the scaffold for the class of chemicals known collectively as [[Dioxins and dioxin-like compounds|dioxins]], which include the potent toxins [[polychlorinated dibenzodioxins]] (PCDDs) such as [[2,3,7,8-Tetrachlorodibenzodioxin|2,3,7,8-tetrachlorodibenzodioxin]].
{{More citations needed|date=December 2021}}
{{reflist}}


== References ==
==External links==
{{Unreferenced|date=November 2009}}
<references/>


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{{Commons category|dibenzo-p-dioxin}}


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{{Commons category|Dibenzo-p-dioxin|lcfirst=yes}}


[[Category:Dibenzodioxins]]
[[Category:Dibenzodioxins]]

[[de:Dibenzodioxin]]
[[fr:Dibenzodioxine]]
[[it:Dibenzodiossina]]
[[hu:Dibenzodioxin]]
[[pl:Dibenzodioksyna]]
[[pt:Dibenzodioxina]]
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