1,2-Dioxin

Names

Systematic IUPAC name

1,2-Dioxine

Identifiers

CAS Number

289-87-2^N

3D model (Jmol)

Interactive image

ChemSpider

10606250^Y

PubChem CID

15559065

InChI

InChI=1S/C4H4O2/c1-2-4-6-5-3-1/h1-4H^Y

Key: VCZQYTJRWNRPHF-UHFFFAOYSA-N^Y
InChI=1/C4H4O2/c1-2-4-6-5-3-1/h1-4H

Key: VCZQYTJRWNRPHF-UHFFFAOYAH

SMILES

O1OC=CC=C1

Properties

Chemical formula

C₄H₄O₂

Molar mass

84.07 g·mol⁻¹

Related compounds

Dibenzodioxin

1,4-Dioxin

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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Infobox references

1,4-Dioxin

1,2-Dioxin is a heterocyclic, organic, antiaromatic compound with the chemical formula C₄H₄O₂. It is an isomeric form of 1,4-dioxin (or p-dioxin).

Due to its peroxide-like characteristics, 1,2-dioxin is very unstable and has not been isolated. Even substituted derivatives are very labile, e.g. 1,4-diphenyl-2,3-benzodioxin. Indeed, in 1990, 3,6-bis(p-tolyl)-1,2-dioxin was wrongly accounted as the first stable derivative. It was subsequently shown that the initial compound was not a derivative of 1,2-dioxin, but a thermodynamically more stable dione.

The isomers 1,2-dioxin (left) and 1,4-dioxin (right)

Structure of the transient 1,4-diphenyl- 2,3-benzodioxin

Dioxin (1) and dione form (2)

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