12-crown-4

Also known as 12-crown-4 ether, EOCT, ethylene oxide cyclic tetramer, 1,4,7,10-tetraoxacyclododecane

12-Crown-4, also called 1,4,7,10-tetraoxacyclododecane and lithium ionophore V, is a crown ether with the formula C8H16O4. It is a cyclic tetramer of ethylene oxide which is specific for the lithium cation.

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Vinony's link graph records 12 inbound references to 12-crown-4, and connects out to International Standard Book Number, mass density and digital object identifier.

Vinony files it under Chembox image size set, Chemical articles with multiple compound IDs and Crown ethers.

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Chemical data

Formula: C8H16O4
Molecular weight: 176.21 g/mol
IUPAC name: 1,4,7,10-tetraoxacyclododecane
SMILES: C1COCCOCCOCCO1
InChIKey: XQQZRZQVBFHBHL-UHFFFAOYSA-N
XLogP: 0
Polar surface area: 36.9 Å²
H-bond donors: 0
H-bond acceptors: 4
Formal charge: 0

via PubChem

Wikidata facts

Subclass of: crown ether
Mass: 176.105

Show 3 more facts

chemical formula: C₈H₁₆O₄
Commons category: 12-crown-4
canonical SMILES: C1COCCOCCOCCO1

Sources (3)

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Encyclopedic overview

4 sections

Contents

Synthesis
Properties
References
See also

== Synthesis == 12-Crown-4 can be synthesized using a modified Williamson ether synthesis, using LiClO4 as a templating cation: (CH2OCH2CH2Cl)2 + (CH2OH)2 + 2 NaOH → (CH2CH2O)4 + 2 NaCl + 2 H2O

Excerpted from Wikipedia’s “12-crown-4” article, available under the CC BY-SA 4.0 licence.