1,2-dioxetane

The chemical substance 1,2-dioxetane (systematically named 1,2-dioxacyclobutane, also known as ethylene peroxide or peroxyethane) is a heterocyclic, organic compound with formula , containing a ring of two adjacent oxygen atoms and two adjacent carbon atoms. It is therefore an organic peroxide, and can be viewed as a dimer of formaldehyde ().

In the Vinony graph

Within Vinony's link graph, 1,2-dioxetane is referenced by 14 other articles, and connects out to oxygen, carbon and carbon dioxide.

It is catalogued under topics including Chemical articles with multiple compound IDs, Dioxetanes and Multiple chemicals in an infobox that need indexing.

Its subject is documented across 15 Wikipedia language editions.

Chemical data

Formula: C2H4O2
Molecular weight: 60.05 g/mol
IUPAC name: dioxetane
SMILES: C1COO1
InChIKey: BVTJGGGYKAMDBN-UHFFFAOYSA-N
XLogP: -0.1
Polar surface area: 18.5 Å²
H-bond donors: 0
H-bond acceptors: 2
Formal charge: 0

via PubChem

Research

296 papers

Energy Transfer Chemiluminescent Spiroadamantane 1,2-Dioxetane Probes for Bioanalyte Detection and Imaging.Angewandte Chemie (International ed. in English) · 2022
Chemiluminescent Probes Based on 1,2-Dioxetane Structures For Bioimaging.Chemistry, an Asian journal · 2022
Phenoxy-1,2-dioxetane-based activatable chemiluminescent probes: tuning of photophysical properties for tracing enzymatic activities in living cells.The Analyst · 2024
Chemiluminescent 1,2-Dioxetane Iridium Complexes for Near-Infrared Oxygen Sensing.Angewandte Chemie (International ed. in English) · 2022
Sensitive detection of fluid biomarkers using adamantylidene 1,2-dioxetane based chemiluminescent probes.Chemical communications (Cambridge, England) · 2025

via PubMed

Wikidata facts

Mass: 60.021

Show 3 more facts

Commons category: 1,2-Dioxetane
chemical formula: C₂H₄O₂
canonical SMILES: C1COO1

Sources (2)

via Wikidata · CC0

~3 min read

Encyclopedic overview

5 sections

Contents

Luminescence
Derivatives
Carbon monoxide generation
See also
References

== Luminescence == Chemiluminescence was first observed with lophine (triphenylimidazole). When in basic solution, this compound converts to the imidazolate, which reacts with oxygen to eventually give the 1,2-dioxetane. Fragmentation of the dioxetane gives the excited state of an anionic diamide.

Excerpted from Wikipedia’s “1,2-dioxetane” article, available under the CC BY-SA 4.0 licence.