Oxirane

The smallest epoxide, with two carbon atoms and one oxygen in a three-membered ring.

Formula
C2H4O
Functional group
Epoxides; Ethers
Molar mass
44.05 g/mol
Also known as
Ethylene oxide, Epoxyethane, 环氧乙烷

Overview

The smallest epoxide, with two carbon atoms and one oxygen in a three-membered ring.

The two ring carbons are equivalent. Ring opening breaks a carbon–oxygen bond and relieves ring strain; addition of water can produce ethylene glycol. This small cyclic ether therefore has different reactivity from an ordinary open-chain ether.

Identifiers

Formula
C2H4O
Functional group
Epoxides; Ethers
Molar mass
44.05 g/mol
Also known as
Ethylene oxide, Epoxyethane, 环氧乙烷
Chemical identifiers
SMILES
C1CO1
InChI
InChI=1S/C2H4O/c1-2-3-1/h1-2H2
PubChem CID
6354

Related compounds

  • Epoxides

    The smallest epoxide, with two carbon atoms and one oxygen in a three-membered ring.

  • Ethers

    The smallest epoxide, with two carbon atoms and one oxygen in a three-membered ring.

References

  1. PubChem Compound Summary: Oxirane (CID 6354)National Center for Biotechnology Information · PubChem

    Identity, molecular formula, molecular weight and selected English aliases retrieved via PUG REST on 2026-09-16. Chinese search names are curated nomenclature translations. Unspecified stereochemistry remains unspecified.

  2. Organic Chemistry: Cyclic Ethers: EpoxidesJohn McMurry · OpenStax Organic Chemistry · 2023

    Supports functional-group chemistry used to curate the linked examples. Checked 2026-09-16; named examples are applications of textbook scope, without claimed experimental yields.

  3. Organic Chemistry: Reactions of Epoxides: Ring-OpeningJohn McMurry · OpenStax Organic Chemistry · 2023

    Supports functional-group chemistry used to curate the linked examples. Checked 2026-09-16; named examples are applications of textbook scope, without claimed experimental yields.