Dibenzo[a,j]-1,4,7,10,13,16-hexaoxacyclooctadeca-2,11-dien
DB18C6 · 6,7,9,10,17,18,20,21-Octahydrodibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecine · ibenzo-18-crown-6 · 6,7,9,10,12,13,15,16-Octahydrodibenzo[b,e][1,4,7,10,13,16]hexaoxacyclooctadecine · crown18 · Crown 18 · crown-18 · Dibenzocrown
![Molekülstruktur von Dibenzo[a,j]-1,4,7,10,13,16-hexaoxacyclooctadeca-2,11-dien](/img/chemical/26541.png)
Identifikatoren & physikalische Daten
| CAS No. | 14187-32-7 |
|---|---|
| Summenformel | C20H24O6 |
| Durchschnittliche Molmasse | 360,4 g/mol |
| Monoisotopische Masse | 360,15728849 g/mol |
| SMILES | c1ccc2c(c1)OCCOCCOc1ccccc1OCCOCCO2 |
| InChIKey | YSSSPARMOAYJTE-UHFFFAOYSA-N |
| PubChem CID | 26541 |
| ChEMBL | CHEMBL345536 |
| ChEBI | CHEBI:358732 |
| EC No. | 238-041-3 |
| DTXSID | DTXSID6022428 |
| Lokaler Name | Dibenzo[a,j]-1,4,7,10,13,16-hexaoxacyclooctadeca-2,11-dien |
Chemische & physikalische Eigenschaften
| XLogP | 2,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 55,4 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 6 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 26 |
| Formalladung | 0 |
| Komplexität | 300 |
| Stoffklassen | Other Classes -> Other Organic Compounds |
| SpringerMaterials Properties | Fusion temperature |
| LogP (Verteilungskoeffizient) | 2.2 |
| Physical Description | Light beige fibers or powder[Alfa Aesar MSDS] |
| Schmelzpunkt | 162-164 °C (lit.) |
| Siedepunkt | 380-384 °C (679 mmHg) |
| Dichte | 1.1801 (rough estimate) |
| Brechungsindex | 1.5200 (estimate) |
| Flammpunkt | 380-384°C/679mm |
| Lagerbedingungen | Store below +30°C. |
| Löslichkeit | 0.007g/lsparingly soluble |
| Aggregatzustand | Fluffy Powder |
| Farbe | White to slightly beige |
| Merck | 14,2602 |
| BRN | 1162153 |
| 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 |
| SMILES | C1COc2ccccc2OCCOCCOc3ccccc3OCCO1 |
| CAS Datenbank | 14187-32-7(CAS DataBase Reference) |
| NIST chemische Informationen | Dibenzo-18-crown-6(14187-32-7) |
| EPA chemische Informationen | Dibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecin, 6,7,9,10,17,18,20,21-octahydro- (14187-32-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315 (35.9%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 64 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Dibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecin, 6,7,9,10,17,18,20,21-octahydro-Dibenzob,k1,4,7,10,13,16hexaoxacyclooctadecin, 6,7,9,10,17,18,20,21-octahydro-: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | A mild skin and moderate eye irritantCauses convulsions, lung changes and other liver changes in oral lethal-dose studies of rats[RTECS] Crown ethers have caused convulsions, liver injury, and dermatitis in experimental animalsA skin and strong eye irritant[Alfa Aesar MSDS] See 18-Crown-6. |
| Hazard Classes and Categories | Skin Irrit. 2 (35.9%) |
| Unerwünschte Wirkungen | Neurotoxin - Other CNS neurotoxin |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29329995 |
| RTECS-Nr. | HP5386000 |
| R-Sätze (R) | 36-36/37/38-20/21/22 |
| Toxizität | LD50 orally in Rabbit: 2600 mg/kg |
| Gefahrensymbole | Xi,Xn |
| hazard_note | Irritant |
| Sicherheitshinweise (S) | 26-37/39-36 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Beschreibung
Dibenzo-18-crown-6 (DB18C6) is the first crown ether synthesized by Pedersen in 1967 and has the strongest binding affinity to a potassium cation (K+) among alkali metal cations. With the similarity of the sizes between K+ and the cavity of crown ether, it had long been believed that the binding selectivity comes from the size relationship between the metal cation and the cavity. However, it was reported that under identical experimental conditions, K+ bound strongly to all crown ethers (12-crown-4 to 24-crown-8) irrespective of the ring size among other cations such as Na+, Ca2+, and NH4+. Moreover, in the gas phase, 18-crown-6 (18C6) and dibenzo18-crown-6 (DB18C6) form preferential complexation in the order Li+ > Na+ > K+ > Rb+ > Cs+, while in the aqueous solution both of them show highest complexion capacity for K+ rather than Li+[1-2].
Verwenden
Dibenzo-18-crown-6, is used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff. It is an important organic intermediate.