Dibenzo-1,4-dioxin

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.

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

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

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

References
  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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