Wikipedia

Dibenzo-1,4-dioxin

See also: 1,4-Dioxin; Dioxins and dioxin-like compounds; and Polychlorinated dibenzodioxins

Dibenzo-1,4-dioxin, also dibenzodioxin or dibenzo-p-dioxin (dibenzo-para-dioxin), is a polycyclic heterocyclic organic compound in which two benzene rings are connected by a 1,4-dioxin ring. Its molecular formula is C12H8O2. The two oxygen atoms occupy opposite (para-) positions in the six-membered dioxin ring.

Dibenzo-p-dioxin
Dibenzodioxin
Ball-and-stick model
Space-filling model
Names
Preferred IUPAC name
Oxanthrene[1]
Other names
Dibenzodioxin,
Dibenzo-p-dioxin,
Dibenzo-1,4-dioxin
Identifiers
3D model (JSmol)
143227
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.432 Edit this at Wikidata
EC Number
  • 205-974-2
280302
KEGG
UNII
UN number 3077
  • InChI=1S/C12H8O2/c1-2-6-10-9(5-1)13-11-7-3-4-8-12(11)14-10/h1-8H checkY
    Key: NFBOHOGPQUYFRF-UHFFFAOYSA-N checkY
  • InChI=1/C12H8O2/c1-2-6-10-9(5-1)13-11-7-3-4-8-12(11)14-10/h1-8H
    Key: NFBOHOGPQUYFRF-UHFFFAOYAJ
  • O1c3c(Oc2c1cccc2)cccc3
Properties
C12H8O2
Molar mass 184.194 g·mol−1
Appearance White crystals
Melting point 122 °C (252 °F; 395 K)
Boiling point 283.5 °C (542.3 °F; 556.6 K)
0.901 g/L (25 °C)
Hazards
GHS labelling:
GHS07: Exclamation markGHS09: Environmental hazard
Warning
H302, H411
P264, P270, P273, P301+P312, P330, P391, P501
Related compounds
Related compounds
 polychlorinated dibenzodioxins ("dioxin"),
dioxins and dioxin-like compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Dibenzodioxin is the carbon skeleton of the poisonous polychlorinated dibenzodioxins (PCDDs), often called dioxins. The most harmful PCDD is 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

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The general name dibenzodioxin usually refers to dibenzo-p-dioxin.

 
Dibenzo-o-dioxin (dibenzo-1,2-dioxin)

The isomeric compound dibenzo-o-dioxin (dibenzo-ortho-dioxin) or dibenzo-1,2-dioxin, like the unstable 1,2-dioxin, has two adjacent oxygen atoms (ortho-). No detailed information is available on this isomer, but it is expected to be highly unstable, with peroxide-like characteristics.

See also

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References

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  1. ^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 216. doi:10.1039/9781849733069-00130. ISBN 978-0-85404-182-4.
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