14174-09-5

Basic information

• Product Name: Dibenzo-24-crown-8
• Synonyms: CROWN ETHER/DIBENZO-24-CROWN-8;[4,4]-DIBENZO-24-CROWN-8;6,7,9,10,12,13,20,21,23,24,26,27-DODECAHYDRODIBENZ[B,N]-1,4,7,10,13,16,19,22-OCTAOXYCYCLOTETRACOSANE;2,3,14,15-DIBENZO-1,4,7,10,13,16,19,22-OCTAOXACYCLOTETRACOSA-2,14-DIENE;Dibenzo-24-crown-8=2,3,14,15-Dibenzo-1,4,7,10,1;Dibenzo-24-crown-8,98%;6,7,9,10,12,13,20,21,23,24,26,27-Dodecahydrodibenz[b,n]-1,4,7,10,13,16,19,22-octaoxacyclotetracosane;2,3,14,15-Dibenzo-1,4,7,10,13,16,19,22-octaoxacyclotetracosa-2,14-diene, 6,7,9,10,12,13,20,21,23,24,26,27-Dodecahydrodibenz[b,n]-1,4,7,10,13,16,19,22-octaoxacyclotetracosane
• CAS NO: 14174-09-5
• Molecular Formula: C₂₄H₃₂O₈
• Molecular Weight: 448.51
• EINECS: 238-027-7
• Product Categories: Crown Ethers;Functional Materials;Macrocycles for Host-Guest Chemistry;crown ether
• Mol File: 14174-09-5.mol
• Article Data: 24

Chemical Properties

• Melting Point: 103-105 °C(lit.)
• Boiling Point: 517.23°C (rough estimate)
• Flash Point: 235.5 °C
• Appearance: white/crystal
• Density: 1.1606 (rough estimate)
• Vapor Pressure: 2.42E-13mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: almost transparency in hot Methanol
• Sensitive: air sensitive
• BRN: 1693744
• CAS DataBase Reference: Dibenzo-24-crown-8(CAS DataBase Reference)
• NIST Chemistry Reference: Dibenzo-24-crown-8(14174-09-5)
• EPA Substance Registry System: Dibenzo-24-crown-8(14174-09-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 14174-09-5(Hazardous Substances Data)

Usage

Chemical Properties

white powder

Purification Methods

Recrystallise it from EtOH, and dry in a vacuum at 60o over P2O5 for 16hours. [Delville et al. J Am Chem Soc 109 7293 1987, V.gtle ed. Top Corr Chem (Host Guest Complex Chemistry) 98 1981.]

InChI:InChI=1/C24H32O8/c1-2-6-22-21(5-1)29-17-13-25-9-10-27-15-19-31-23-7-3-4-8-24(23)32-20-16-28-12-11-26-14-18-30-22/h1-8H,9-20H2

Upstream product

• 120-80-9 benzene-1,2-diol 
• 112-26-5 1,2-bis(2-chloroethoxy)ethane 
• 540495-04-3 C₇H₈O₃S*C₁₄H₁₅N*C₂₄H₃₂O₈ 
• 19249-03-7 triethylene glycol di-(p-toluenesulfonate) 
• 77544-68-4 8-tosyloxy-3,6-dioxaoctanol 
• 88037-68-7 1,2-bis{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}benzene 
• 240797-46-0 1,2-bis{2-[2-(2-tosylethoxy)ethoxy]ethoxy}benzene 

Downstream Products

• 17455-23-1 cis-syn-cis dicyclohexano-24-crown-8 
• 102101-76-8 2,5,8,11,18,21,24,27-Octaoxa-tricyclo[26.4.0.0^12,17]dotriaconta-1⁽³²⁾,12⁽¹⁷⁾,13,15,28,30-hexaene; compound with picric acid 
• 121561-12-4 m,m'-ditosyldibenzo-24-crown-8 
• 121561-14-6 m,m'-ditosyldibenzo-24-crown-8 

Relevant articles and documents

Conductance study of binding of some Rb+ and Cs+ ions by macrocyclic polyethers in acetonitrile solution

A conductance study of the interaction between Rb+ and Cs+ ions and 18-crown-6 (18C6), dicyclohexyl-18-crown-6 (DC18C6), dibenzo-18-crown-6 (DB18C6), dibenzo-24-crown-8 (DB24C8), and dibenzo-30-crown-10 (DB30C10) in acetonitrile solution has been carried out at various temperatures. The formation constants of the resulting 1:1 complexes were determined from the molar conductance-mole ratio data and found to vary in the order DC18C6 > 18C6 > DB30C10 > DB18C6 ～ DB24C8 for Rb+ ion and DC18C6 > 18C6 > DB30C10 ～ DB24C8 > DB18C6 for Cs+ ion. The enthalpy and entropy of complexation were determined from the temperature dependence of the formation constants. The complexes with the 18-crowns are both enthalpy and entropy stabilized while, in the case of large crown ethers, the corresponding complexes are enthalpy stabilized but entropy destabilized.

Which One is Bulkier: The 3,5-Dimethylphenyl or the 2,6-Dimethylphenyl Group? Development of Size-Complementary Molecular and Macromolecular [2]Rotaxanes

We developed novel size-complementary molecular and macromolecular rotaxanes using a 2,6-dimethylphenyl terminal group as the axle-end-cap group in dibenzo-24-crown-8-ether (DB24C8)-based rotaxanes, where the 2,6-dimethylphenyl group was found to be less bulky than the 3,5-dimethylphenyl group. A series of molecular and macromolecular [2]rotaxanes that bear a 2,6-dimethylphenyl group as the axle-end-cap were synthesized using unsubstituted and fluorine-substituted DB24C8. Base-induced decomposition into their constituent components confirmed the occurrence of deslipping, which supports the size-complementarity of these rotaxanes. The deslipping rate was independent of the axle length but dependent on the DB24C8 substituents. A kinetic study indicated the rate-determining step was that in which the wheel is getting over the end-cap group, and deslipping proceeded via a hopping-over mechanism. Finally, the present deslipping behavior was applied to a stimulus-degradable polymer as an example for the versatile utility of this concept in the context of stimulus-responsive materials.

Interactions between protonated Amine, aza crown ether, and cryptand with dibenzocrown ether studied by a new spectrophotometric technique

The stability constants for the complexation of a diprotonated diamine, a diaza crown ether, and a cryptand with dibenzo-18-crown-6 and dibenzo-24-crown-8, have been studied in aqueous solution using a new spectrophotometric technique. Because of the complex formation, the solubility of the dibenzocrown ethers increases. Complex formation is possible between diamines and dibenzocrown ethers with both 1:1 and 2:1 stoichiometry. However, experimental data are insufficient to decide on the actual stoichiometry of the complexes formed. By computing the stability constants and comparing them with the corresponding results for monoamines, it is possible to decide on the actual stoichiometry of the complexes. Under the experimental conditions only 1:1 complexes with diamines are formed.

Disaggregation reaction of [2]Pseudorotaxanes composed of dibenzo[24]crown-8 and dialkylammonium having isopropyl end groups

[2]Pseudorotaxanes composed of dibenzo[24]crown-8 (DB24C8) and dialkylammonium having isopropyl end groups are converted into the component molecules in C6D6 solution containing PF6 - anion.

Synthesis of Isomeric Dinitro and Diamino Derivatives of Polycyclic Crown Ethers: Dibenzo-18-crown-6 and Dibenzo-24-crown-8

Specific features of the synthesis of polycyclic crown ethers dibenzo-18-crown-6 and dibenzo-24-crown-8 and their dinitro and diamino derivatives have been studied. A mixture of isomers of dibenzocrown ether derivatives was obtained and separated. The spectral and thermal characteristics of the synthesized compounds and the kinetics of synthesis of dibenzo-24-crown-8 by the two-component condensation of pyrocatechol with 1-chloro-2-[2-(2-chloroethoxy)ethoxy]ethane in an alcoholic medium in the presence of a KOH template agent were studied.