Dibenzo-1,4-dioxin

Dibenzo-p-dioxin
Dibenzodioxin
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
CAS Number
3D model (JSmol)
Beilstein Reference
 143227
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.432
EC Number
  • 205-974-2
Gmelin Reference
 280302
KEGG
PubChem CID
UNII
UN number 3077
CompTox Dashboard (EPA)
InChI
  • 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
SMILES
  • O1c3c(Oc2c1cccc2)cccc3
Properties
Chemical formula
 C12H8O2
Molar mass 184.194 g·mol−1
Appearance White crystals
Density 1.243 kg/m3[2]
Melting point 122 °C (252 °F; 395 K)
Boiling point 283.5 °C (542.3 °F; 556.6 K)
Solubility in water
 0.901 g/L (25 °C)
Hazards
GHS labelling:
Pictograms
 GHS07: Exclamation markGHS09: Environmental hazard
Signal word
 Warning
Hazard statements
 H302, H411
Precautionary statements
 P264, P270, P273, P301+P312, P330, P391, P501
Lethal dose or concentration (LD, LC):
LD50 (median dose)
 866 mg/kg (mouse, oral)[2]
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

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.

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.
  2. ^ a b "DIBENZO-P-DIOXIN - Safety Data Sheet". www.chemicalbook.com.
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