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12-crown-4 skeletal.svg
12-Crown-4 molecule
IUPAC name
Other names
12-crown-4, Lithium Ionophore V
294-93-9 YesY
ChEBI CHEBI:32399 YesY
ChemSpider 8912 YesY
Jmol-3D images Image
Molar mass 176.21
Density 1.089 g/mL at 25 deg C
Melting point 16 deg C
Boiling point 61-70 deg C/0.5 mm Hg
Flash point 113 °C (235 °F; 386 K)
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

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. Its point group is S4. The dipole moment of 12-crown-4 varies in different solvent and under different temperature. Under 25 °C, the dipole moment of 12-crown-4 was determined as 2.33 ± 0.03 D in cyclohexane and 2.46 ± 0.01 D in benzene.[1]

Ball-and-stick model of the bis(12-crown-4)lithium cation


  1. ^ Caswell, Lyman R.; Savannunt, Diana S. (January 1988). "Temperature and solvent effects on the experimental dipole moments of three crown ethers". Journal of Heterocyclic Chemistry 25 (1): 73–79. doi:10.1002/jhet.5570250111. 

See also[edit]

  • Crown ether
  • Cyclen, a similar molecule with N atoms (aza groups) instead of O atoms (ethers)