Dibenzo[a,j]-1,4,7,10,13,16-hexaoxacyclooctadeca-2,11-dien

Dibenzo-18-crown-6

HCID 26541CAS 14187-32-7
TeilstruktursucheÄhnliche Strukturen suchen

Grundinformationen

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

Datenbank-Bezeichner

CAS
14187-32-7
PubChem CID
26541
DTXSID
DTXSID6022428
ChEMBL
CHEMBL345536
ChEBI
CHEBI:358732
UNII
0A7W45JCS9
EC Number
238-041-3
Nikkaji
J14.747H

Eigenschaften

Berechnete Struktureigenschaften

XLogP
2,2
Polarare Oberfläche (TPSA)
55,4 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
0
Schwere Atome
26

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.

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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 · 2 Einträge

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 · 1 Eintrag

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
tsca
TSCA listed
hs_code
29329995
RTECS-Nr.
HP5386000
risk_code
36-36/37/38-20/21/22
Toxizität
LD50 orally in Rabbit: 2600 mg/kg

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 · 2 Einträge

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.

Vor- und nachgelagerte Produkte

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