2,5,8,15,18,21-hexaoxatricyclo[20.4.0.0^{9,14}]hexacosane

• ChemBase ID: 53604
• Molecular Formular: C20H36O6
• Molecular Mass: 372.49624
• Monoisotopic Mass: 372.25118887
• SMILES: O1C2C(OCCOCCOC3C(OCCOCC1)CCCC3)CCCC2
• Canonical SMILES: O1CCOC2CCCCC2OCCOCCOC2C(OCC1)CCCC2
• InChI: InChI=1S/C20H36O6/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/h17-20H,1-16H2
• InChIKey: BBGKDYHZQOSNMU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5,8,15,18,21-hexaoxatricyclo[20.4.0.0^{9,14}]hexacosane; 2,5,8,15,18,21-hexaoxatricyclo[20.4.0.0^9,^1^4]hexacosane
• IUPAC Traditional name: dicyclohexyl-18-crown-6
• Synonyms: Icosahydrodibenzo[b,k][1,4,7,10,13,16]-hexaoxacyclooctadecine; 2,3,11,12-Dicyclohexano-1,4,7,10,13,16-hexaoxacyclooctadecane; 2,5,8,15,18,21-Hexaoxatricyclo[20.4.0.09.14]hexacosane; Perhydro-dibenzo-18-crown-6; Dicyclohexano-18-crown-6; Dicyclohexano-18-crown-6, mixture of isomers; Dicyclohexyl-18-Crown-6; DICYCLOHEXANO-18-CROWN-6; icosahydrodibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecine; 2,3,11,12-双环己基-1,4,7,10,13,16-六氧环十八烷; 2,5,8,15,18,21-六氧杂三环[20.4.0.09.14]二十六烷; 二环己基并-18-冠醚-6; 全氢-二苯并-18-冠-6; 二环己烷并-18-冠醚-6; 二环己烷并-18-冠-6, 异构体混合物

Database IDs

• CAS Number: 16069-36-6
• EC Number: 240-216-4
• MDL Number: MFCD00005099
• Beilstein Number: 1130529
• Merck Index: 142602
• PubChem SID: 24862683; 24849733; 162058367
• PubChem CID: 85955

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 2.5470848
• LogD (pH = 7.4): 2.5470848
• Log P: 2.5470848
• Molar Refractivity: 98.4278 cm^3
• Polarizability: 39.571877 Å^3
• Polar Surface Area: 55.38 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 46-53°C; 47-50 °C
• Flash Point: >110°C(230°F); 113 °C; 235.4 °F

Safety Information

• Storage Condition: 2-8°C
• Storage Warning: Hygroscopic; IRRITANT
• RTECS: HP5385000
• European Hazard Symbols: Toxic (T); Irritant (Xi)
• UN Number: 2811; UN2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Australian Hazchem: 2X
• Risk Statements: 23/24/25-36/37/38; 24/25-36; R:25-36
• Safety Statements: 26-36/37/39-45; 26-36/37-45; S:28-29-36/37/39-45
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: false; 是
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H315-H319-H331-H335; H301-H311-H319
• GHS Precautionary statements: P261-P280-P301 + P310-P305 + P351 + P338-P311; P280H-P305+P351+P338-P309-P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

Product Information

• Purity: ≥97.0% (GC); 97%; 98%
• Grade: purum
• Impurities: ≤2% dibenzo-18-crown-6
• Empirical Formula (Hill Notation): C20H36O6

DETAILS

MP Biomedicals - 02157662

Purity: 98%
Mixed Isomers

Sigma Aldrich - 158402

Packaging
1, 10 g in glass bottle
Application
Anion activator,1 and complexing agent which solubilizes alkali metal ions in non-polar solvents.2,3

Sigma Aldrich - 36665

Other Notes
Macrocyclic complexing agent for cations1

REFERENCES

• Crown ether (see Appendix 2). Increases the rate of acetolysis of benzyl chloride in acetonitrile by a factor of >400: Synthesis, 117 (1981).
• In combination with potassium permanganate, effects the stereoselective cis-hydroxylation of a double bond from the less-hindered side: Chem. Lett., 173 (1983).