Oxepine

Oxepine

Names
Preferred IUPAC name Oxepine
Other names Oxacycloheptatriene
Identifiers
CAS Number	291-70-3 Y
3D model (JSmol)	Interactive image
ChemSpider	4953942 Y
ECHA InfoCard
E number
PubChem CID	6451477
UNII	CVP5X85XX5 Y
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI InChI=1S/C6H6O/c1-2-4-6-7-5-3-1/h1-6H ☒N Key: ATYBXHSAIOKLMG-UHFFFAOYSA-N ☒N InChI=1/C6H6O/c1-2-4-6-7-5-3-1/h1-6H Key: ATYBXHSAIOKLMG-UHFFFAOYAS
SMILES C1=CC=COC=C1
Properties
Chemical formula	C6H6O
Molar mass	94.113 g·mol−1
Related compounds
Related compounds	Cyclohexene oxide Oxonane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). ☒N verify (what is Y☒N ?) Infobox references

Oxepine is an oxygen-containing heterocycle consisting of a seven-membered ring with three double bonds. The parent C₆H₆O exists as an equilibrium mixture with benzene oxide.

File:Oxepin-benzene oxide.png

The oxepin–benzene oxide equilibrium is affected by the ring substituents. A related dimethyl derivative exists mainly as the oxepine isomer, an orange liquid.

In nature, oxepine is an intermediate in the oxidation of benzene by the cytochrome P450 (CYP). Other arene oxides are metabolites of the parent arene.

Formation and selected reactions of benzene oxide (2) and oxepin (3)

Benzene oxides are produced in the laboratory from dehydrohalogenation of the corresponding dihaloepoxide:

Oxepin synthesis