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Dibenzo-18-crown-6

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Dibenzo-18-crown-6 Basic information
Product Name:Dibenzo-18-crown-6
Synonyms:CROWN ETHER/DIBENZO-18-CROWN-6;DIBENZO-18-CROWN-6;dibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecin,6,7,9,10,17,18,20,21-octahyd;dibenzo[bk][1,4,7,10,13,16]hexaoxacyclooctadecane;Dibenzocrown;Diphenyl-18-crown-6-polyether;k](1,4,7,10,13,16)hexaoxacyclooctadecin,6,7,9,10,17,18,20,21-octahydro-Dibenzo[b;6,7,9,10,12,13,20,21-Octahydrodibenzo[b,k][1,4,7,10,13,16]hexaoxacyclo-octadecin
CAS:14187-32-7
MF:C20H24O6
MW:360.4
EINECS:238-041-3
Product Categories:crown ether;API intermediates;Crown Ethers;Functional Materials;Macrocycles for Host-Guest Chemistry
Mol File:14187-32-7.mol
Dibenzo-18-crown-6 Structure
Dibenzo-18-crown-6 Chemical Properties
Melting point 162-164 °C (lit.)
Boiling point 380-384 °C (679 mmHg)
density 1.1801 (rough estimate)
refractive index 1.5200 (estimate)
Fp 380-384°C/679mm
storage temp. Store below +30°C.
solubility 0.007g/l
form Fluffy Powder
color White to slightly beige
Water Solubility sparingly soluble
Sensitive air sensitive
λmax277nm(CH2Cl2)(lit.)
Merck 14,2602
BRN 1162153
InChIKeyYSSSPARMOAYJTE-UHFFFAOYSA-N
CAS DataBase Reference14187-32-7(CAS DataBase Reference)
NIST Chemistry ReferenceDibenzo-18-crown-6(14187-32-7)
EPA Substance Registry SystemDibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecin, 6,7,9,10,17,18,20,21-octahydro- (14187-32-7)
Safety Information
Hazard Codes Xi,Xn
Risk Statements 36-36/37/38-20/21/22
Safety Statements 26-37/39-36
WGK Germany 2
RTECS HP5386000
Hazard Note Irritant
TSCA Yes
HS Code 29329995
ToxicityLD50 orally in Rabbit: 2600 mg/kg
MSDS Information
Dibenzo-18-crown-6 Usage And Synthesis
DescriptionDibenzo-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].
Chemical Propertieswhite to slightly beige fluffy powder
UsesCrown ether/Dibenzo-18-crown-6 for synthesis. CAS 14187-32-7, molar mass 360.41 g/mol.
UsesDibenzo-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.
DefinitionChEBI: 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.
Purification MethodsCrystallise it from *benzene, n-heptane or toluene and dry it under vacuum at room temperature for several days. [Szezygiel J Phys Chem 91 1252 1987, V.gtle ed. Top Corr Chem (Host Guest Complex Chemistry) 98 1981.]
References [1] Pooja Sahu, Jayant K. Singh, Sk. M. Ali. “Structural and dynamical properties of Li+-dibenzo-18-crown-6(DB18C6) complex in pure solvents and at the aqueous-organic interface.” Journal of Molecular Modeling 20 9 (2014).
[2] Chang Min Choi, Nam Joon Kim, Jiyoung Heo. “Binding selectivity of dibenzo-18-crown-6 for alkali metal cations in aqueous solution: A density functional theory study using a continuum solvation model.” Chemistry Central Journal 6 1 (2012): 84.
Tag:Dibenzo-18-crown-6(14187-32-7) Related Product Information
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