18-Crown-6

18-Crown-6
Names
	Preferred IUPAC name 1,4,7,10,13,16-Hexaoxacyclooctadecane
Identifiers
CAS Number	17455-13-9 ;
3D model (JSmol)	Interactive image; Interactive image;
Beilstein Reference	1619616
ChEBI	CHEBI:32397 ;
ChEMBL	ChEMBL155204 ;
ChemSpider	26563 ;
ECHA InfoCard	100.037.687
EC Number	241-473-5;
Gmelin Reference	4535
PubChem CID	28557;
UNII	63J177NC5B ;
CompTox Dashboard (EPA)	DTXSID7058626 ;
	InChI InChI=1S/C12H24O6/c1-2-14-5-6-16-9-10-18-12-11-17-8-7-15-4-3-13-1/h1-12H2 Key: XEZNGIUYQVAUSS-UHFFFAOYSA-N ; InChI=1/C12H24O6/c1-2-14-5-6-16-9-10-18-12-11-17-8-7-15-4-3-13-1/h1-12H2 Key: XEZNGIUYQVAUSS-UHFFFAOYAP;
	SMILES O1CCOCCOCCOCCOCCOCC1; C1COCCOCCOCCOCCOCCO1;
Properties
Chemical formula	C12H24O6
Molar mass	264.315 g/mol
Density	1.237 g/cm3
Melting point	37 to 40 °C (99 to 104 °F; 310 to 313 K)
Boiling point	116 °C (241 °F; 389 K) (0.2 Torr)
Solubility in water	75 g/L
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H315, H319, H335
Precautionary statements	P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
Related compounds
Related compounds	Dibenzo-18-crown-6; Triglyme; Hexaaza-18-crown-6
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

18-Crown-6 is an organic compound with the formula [C₂H₄O]₆ and the IUPAC name of 1,4,7,10,13,16-hexaoxacyclooctadecane. It is a white, hygroscopic crystalline solid with a low melting point.^[1] Like other crown ethers, 18-crown-6 functions as a ligand for some metal cations with a particular affinity for potassium cations (binding constant in methanol: 10⁶ M⁻¹). The point group of 18-crown-6 is S₆. The dipole moment of 18-crown-6 is solvent- and temperature-dependent. Below 25 °C, the dipole moment of 18-crown-6 is 2.76 ± 0.06 D in cyclohexane and 2.73 ± 0.02 in benzene.^[2] The synthesis of the crown ethers led to the awarding of the Nobel Prize in Chemistry to Charles J. Pedersen.

^ Steed, Jonathan W.; Atwood, Jerry L. (2009). Supramolecular Chemistry (2nd ed.). Wiley. ISBN 978-0-470-51233-3.
^ Caswell, Lyman R.; Savannunt, Diana S. (January 1988). "Temperature and solvent effects on the experimental dipole moments of three crown ethers". J. Heterocyclic Chem. 25 (1): 73–79. doi:10.1002/jhet.5570250111.

[SupraChem-1] Steed, Jonathan W.; Atwood, Jerry L. (2009). Supramolecular Chemistry (2nd ed.). Wiley. ISBN 978-0-470-51233-3.

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

[1]

[2]