12-Crown-4

12-Crown-4

Names
IUPAC name 1,4,7,10-tetraoxacyclododecane
Other names 12-crown-4, Lithium Ionophore V
Identifiers
CAS Number	294-93-9
ChEBI	CHEBI:32399
ChemSpider	8912
Jmol interactive 3D	Image Image
InChI InChI=1S/C8H16O4/c1-2-10-5-6-12-8-7-11-4-3-9-1/h1-8H2 Key: XQQZRZQVBFHBHL-UHFFFAOYSA-N InChI=1/C8H16O4/c1-2-10-5-6-12-8-7-11-4-3-9-1/h1-8H2 Key: XQQZRZQVBFHBHL-UHFFFAOYAA
SMILES O1CCOCCOCCOCC1 C1COCCOCCOCCO1
Properties
Chemical formula	C8H16O4
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
Hazards
Flash point	113 °C (235 °F; 386 K)
Except where otherwise noted, data are 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]

References

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.

• Sigma-Aldrich Handbook of Fine Chemicals, 2007, page 768.

See also

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