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.

Dibenzo-p-dioxin
Names



Preferred IUPAC name Oxanthrene
Other names Dibenzodioxin, Dibenzo-p-dioxin, Dibenzo-1,4-dioxin
Identifiers
CAS Number	262-12-4^Y
3D model (JSmol)	Interactive image
Beilstein Reference	143227
ChEBI	CHEBI:28891
ChEMBL	ChEMBL3184198
ChemSpider	8861^Y
ECHA InfoCard	100.005.432
EC Number	205-974-2
Gmelin Reference	280302
KEGG	C07732^Y
PubChem CID	9216
UNII	O1B5KJ235I
UN number	3077
CompTox Dashboard (EPA)	DTXSID8020410
InChI InChI=1S/C12H8O2/c1-2-6-10-9(5-1)13-11-7-3-4-8-12(11)14-10/h1-8H^Y Key: NFBOHOGPQUYFRF-UHFFFAOYSA-N^Y 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
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
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)
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). Y verify (what is ^YN ?) 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.

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.

Isomer

See also