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.

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.