2,5,8,15,18,21-hexaoxatricyclo[20.4.0.0^{9,14}]hexacosa-1(22),9(14),10,12,23,25-hexaene

• ChemBase ID: 75101
• Molecular Formular: C20H24O6
• Molecular Mass: 360.40096
• Monoisotopic Mass: 360.15728849
• SMILES: O1c2c(cccc2)OCCOCCOc2c(cccc2)OCCOCC1
• Canonical SMILES: O1CCOc2ccccc2OCCOCCOc2c(OCC1)cccc2
• InChI: InChI=1S/C20H24O6/c1-2-6-18-17(5-1)23-13-9-21-11-15-25-19-7-3-4-8-20(19)26-16-12-22-10-14-24-18/h1-8H,9-16H2
• InChIKey: YSSSPARMOAYJTE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5,8,15,18,21-hexaoxatricyclo[20.4.0.0^{9,14}]hexacosa-1(22),9(14),10,12,23,25-hexaene; 2,5,8,15,18,21-hexaoxatricyclo[20.4.0.0^9,^1^4]hexacosa-1(26),9,11,13,22,24-hexaene; 2,5,8,15,18,21-hexaoxatricyclo[20.4.0.0^9,^1^4]hexacosa-1(22),9,11,13,23,25-hexaene; 2,5,8,15,18,21-hexaoxatricyclo[20.4.0.0^9,^1^4]hexacosa-1(22),9(14),10,12,23,25-hexaene; 2,5,8,15,18,21-hexaoxatricyclo[20.4.0.0^{9,14}]hexacosa-1(26),9,11,13,22,24-hexaene
• IUPAC Traditional name: 2,5,8,15,18,21-hexaoxatricyclo[20.4.0.0^{9,14}]hexacosa-1(22),9(14),10,12,23,25-hexaene; 2,5,8,15,18,21-hexaoxatricyclo[20.4.0.0^9,^1^4]hexacosa-1(22),9(14),10,12,23,25-hexaene; dibenzo-18-crown-6
• Synonyms: Dibenzo-18-crown-6-ether; Dibenzo-18-crown-6; 2,5,8,15,18,21-hexaoxatricyclo[20.4.0.0^{9,14}]hexacosa-1(22),9(14),10,12,23,25-hexaene; 6,7,9,10,17,18,20,21-octahydrodibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecine; 6,7,9,10,17,18,20,21-Octahydrodibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecene; 2,3,11,12-Dibenzo-1,4,7,10,13,16-hexaoxacyclooctadeca-2,11-diene; DIBENZO-18-CROWN-6; Dibenzo-18-crown-6; Tin(II) ionophore I; 2,3,11,12-二苯并-1,4,7,10,13,16-六氧杂环十八-2,11-二烯; 6,7,9,10,17,18,20,21-八氢二苯并[b,k][1,4,7,10,13,16]六氧杂环十八碳烯; 二苯并-18-冠醚-6; 二苯并-18-冠醚-6; 锡(II) 离子载体 I; 二苯并-18-冠-6醚

Database IDs

• CAS Number: 14187-32-7
• EC Number: 238-041-3
• MDL Number: MFCD00005098
• Beilstein Number: 1162153
• Merck Index: 142602
• PubChem SID: 24860303; 24849732; 162040019
• PubChem CID: 26541
• CHEBI ID: 358732
• CHEMBL: 345536
• Chemspider ID: 24722
• KEGG ID: C14289
• Wikipedia Title: Dibenzo-18-crown-6

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 2.8788056
• LogD (pH = 7.4): 2.8788056
• Log P: 2.8788056
• Molar Refractivity: 96.1178 cm^3
• Polarizability: 38.03511 Å^3
• Polar Surface Area: 55.38 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 160-164°C; 161-163 °C; 162-164 °C(lit.); 162-164°C; 163 - 164°C
• Boiling Point: 380-384°C/679mm
• Hydrophobicity(logP): 3.488

Safety Information

• Storage Condition: 2-8°C
• Storage Warning: Irritant
• RTECS: HP5386000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36; 36/37/38; R:36/37/38
• Safety Statements: 26; 26-37; S:20-25-26-37/39
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335; H319
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A; P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (UV); 95%; 95+%; 98%; 98+%
• Grade: purum; Selectophore™
• Empirical Formula (Hill Notation): C20H24O6

DETAILS

MP Biomedicals - 02150847

Off-white to gray crystals.
A crown ether that acts as a complexing agent which solubilizes alkali metal ions in non-polar solvents.

Sigma Aldrich - 158399

Application
Phase-transfer catalyst employed in monoazaporphyrin syntheses.1 Agent used for ion transfer across membranes2 and as a synthon for preparation of liquid crystal polyesters.3
Packaging
2.5, 10, 50 g in glass bottle

Sigma Aldrich - 33531

Other Notes
Macrocyclic complexing agent for cations1

Sigma Aldrich - 49902

General description
Visit our Sensor Applications portal to learn more.
Legal Information
Selectophore is a trademark of Sigma-Aldrich GmbH

REFERENCES

• Catalyst for the formation of phenacyl esters from phenacyl bromides and K salts of carboxylic acids in acetonitrile: Synth. Commun., 26, 1747 (1996).
• Catalyst for the halogenative cleavage of epoxides with Br₂ or I₂, giving halohydrins in high yields: J. Org. Chem., 63, 1455 (1998).
• See also 18-Crown-6, A11249 and Appendix 2.
• Comparison of the rates of displacement of F^- in 1-fluoro-2- or 4-nitrobenzene with KOMe and KO-t-Bu in the presence of this crown ether gave a result (t-BuO^- >> MeO^-) opposite to the pattern observed in its absence: J. Chem. Soc., Perkin 2, 55 (1973).
• Promotes the generation of bromochlorocarbene from Chlorodibromomethane, A16938: Syntheis, 783 (1977); Tetrahedron, 33, 363 (1977), and of dibromocarbene from Bromoform, A11904: Org. Synth., 75, 98 (1997).
• In combination with Benzyltriethylammonium chloride, A13268, promotes the oxidative decarboxylation of arylacetic acids with NaIO₄ to give high yields of the aryl aldehydes: Indian J. Chem. B, 35B, 151 (1996). Under the same conditions, phenacyl bromides are converted to benzoic acids.