Dibenzo[a,j]-1,4,7,10,13,16-hexaoxacyclooctadeca-2,11-dien
Dibenzo-18-crown-6
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Grundinformationen
- CAS
14187-32-7- Standard-SMILES
c1ccc2c(c1)OCCOCCOc1ccccc1OCCOCCO2- InChIKey
YSSSPARMOAYJTE-UHFFFAOYSA-N- Summenformel
- C20H24O6
- Durchschnittliche Molmasse
- 360,4 g/mol
- Monoisotopische Masse
- 360,15728849
Überblick
Dibenzo-18-crown-6 is a crown ether that is 18-crown-6 ortho-fused to two benzene rings at positions 8-9 and 17-18. It has a role as a phase-transfer catalyst. It is a member of benzenes and a crown ether.
Namen und Bezeichner
- Bevorzugter Name
- Dibenzo-18-crown-6
- IUPAC
- 2,5,8,15,18,21-hexaoxatricyclo[20.4.0.09,14]hexacosa-1(26),9,11,13,22,24-hexaene
- Lokaler Name
- Dibenzo[a,j]-1,4,7,10,13,16-hexaoxacyclooctadeca-2,11-dien
- Englischer Name
- Dibenzo-18-crown-6
- Summenformel
- C20H24O6
- Molmasse
- 360.4
Namen und Synonyme
DIBENZO-18-CROWN-614187-32-7Dibenzo-18-crown-6-etherCrown 18Dibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecin, 6,7,9,10,17,18,20,21-octahydro-2,3:11,12-Dibenzo-1,4,7,10,13,16-hexaoxacyclooctadecane0A7W45JCS9Dibenzo(b,k)(1,4,7,10,13,16)hexaoxacyclooctadecane2,5,8,15,18,21-hexaoxatricyclo[20.4.0.09,14]hexacosa-1(26),9,11,13,22,24-hexaeneNSC-147771Dibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecaneDTXSID6022428
Weitere Namen anzeigen
DB18C6ibenzo-18-crown-66,7,9,10,12,13,15,16-Octahydrodibenzo[b,e][1,4,7,10,13,16]hexaoxacyclooctadecinecrown18crown-18DibenzocrownDibenzo-18-crown-8
CHEBI:358732Dibenzo(b,k)(1,4,7,10,13,16)hexaoxacyclooctadecin, 6,7,9,10,17,18,20,21-octahydro-2,5,8,15,18,21-hexaoxatricyclo(20.4.0.09,14)hexacosa-1(26),9,11,13,22,24-hexaeneRefChem:132840DTXCID802428238-041-36,7,9,10,17,18,20,21-Octahydrodibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecineMFCD00005098
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 2,2
- Polarare Oberfläche (TPSA)
- 55,4 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 6
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 26
- Formalladung
- 0
- Komplexität
- 300
Experimentelle und physikochemische Eigenschaften
Chemical ClassesOther Classes -> Other Organic Compounds
SpringerMaterials PropertiesFusion temperature
LogP2.2
Physical DescriptionLight beige fibers or powder; [Alfa Aesar MSDS]
Physikochemische Eigenschaften
- Schmelzpunkt
- 162 · 162-164 °C (lit.)
- Siedepunkt
- 380 · 380-384 °C (679 mmHg)
- Dichte
- 1.1801 · 1.1801 (rough estimate)
- Brechungsindex
- 1.52 · 1.5200 (estimate)
- Flammpunkt
- 380 · 380-384°C/679mm
- storage temp.
- 30 °C · Store below +30°C.
- Löslichkeit
- 0.007 g/l · 0.007g/l
- Aggregatzustand
- Fluffy Powder
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Warning
H315 (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.
Gefahrenhinweise
Regulatory Information
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
Hazards Summary
A mild skin and moderate eye irritant; Causes 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 animals; A skin and strong eye irritant; [Alfa Aesar MSDS] See 18-Crown-6.
Hazard Classes and CategoriesSkin Irrit. 2 (35.9%)
Toxikologische Informationen
Adverse EffectsNeurotoxin - Other CNS neurotoxin
Sicherheitsdaten
- wgk
- 2
Chemie und Industrie
Verwendung und Herstellung
General Manufacturing InformationDibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecin, 6,7,9,10,17,18,20,21-octahydro-: ACTIVE
Anwendungen
BeschreibungDibenzo-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].
VerwendenDibenzo-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.
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