14098-41-0

Basic information

• Product Name: [2,5]-DIBENZO-21-CROWN-7
• Synonyms: [2,5]-DIBENZO-21-CROWN-7;[3,4]-DIBENZO-21-CROWN-7;6,7,9,10,12,13,20,21,23,24-DECAHYDRODIBENZO[B,K][1,4,7,10,13,16,19]HEPTAOXACYCLO HENEICOSIN;6,7,10,12,13,15,16,23,24-DECAHYDRODIBENZO[B,H][1,4,7,10,13,16,19]HEPTAOXACYCLOHENEICOSIN;DIBENZO-21-CROWN-7;DIBENZO-21-CROWN 7-ETHER;3,4-DIBENZO-21-CROWN-7 98%;[3,4]-Dibenzo-21-crown-7,98%
• CAS NO: 14098-41-0
• Molecular Formula: C₂₂H₂₈O₇
• Molecular Weight: 404.45
• Product Categories: Crown Ethers;Functional Materials;Macrocycles for Host-Guest Chemistry;Chelation/Complexation Compounds;Crown Ethers;Synthetic Reagents
• Mol File: 14098-41-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 103-107 °C(lit.)
• Boiling Point: 486.07°C (rough estimate)
• Flash Point: 221.6°C
• Appearance: White/Fluffy Amorphous Powder
• Density: 1.1710 (rough estimate)
• Vapor Pressure: 1.58E-11mmHg at 25°C
• Refractive Index: 1.6380 (estimate)
• Solubility: almost transparency in hot Toluene
• BRN: 1693830
• CAS DataBase Reference: [2,5]-DIBENZO-21-CROWN-7(CAS DataBase Reference)
• NIST Chemistry Reference: [2,5]-DIBENZO-21-CROWN-7(14098-41-0)
• EPA Substance Registry System: [2,5]-DIBENZO-21-CROWN-7(14098-41-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• WGK Germany: 3
• Hazardous Substances Data: 14098-41-0(Hazardous Substances Data)

Usage

Chemical Properties

white fluffy amorphous powder

InChI:InChI=1/C22H28O7/c1-3-7-21-19(5-1)26-15-11-23-9-10-24-12-16-27-20-6-2-4-8-22(20)29-18-14-25-13-17-28-21/h1-8H,9-18H2

Upstream product

• 23116-94-1 bis(2-hydroxyphenoxyethyl)ether 
• 112-26-5 1,2-bis(2-chloroethoxy)ethane 
• 82645-24-7 1,5-bis(benzaldehydeoxy)-3-oxopentane 
• 90-02-8 salicylaldehyde 
• 80322-82-3 triethyleneglycol dimesylate 
• 34604-52-9 diethylene glycol dimesylate 
• 68822-97-9 1,8-bis(2-hydroxyphenoxy)-3,6-dioxaoctane 
• 87117-71-3 2,2'-<1,2-Ethandiylbis(oxy-2,1-ethandiyloxy)>bisphenol-dibenzylether 
• 7460-82-4 diethylene glycol ditosylate 

Downstream Products

• 17455-21-9 dicyclohexano-21-crown-7 

Relevant articles and documents

Application of Bayer-Villiger reaction to the synthesis of dibenzo-18-crown-6, dibenzo-21-crown-7 and dihydroxydibenzo-18-crown-6

Dibenzo-18-crown-6, dibenzo-21-crown-7 and dihydroxy dibenzo-18-crown-6 were synthesized by Bayer-Villiger oxidation strategy. Dibenzo-18-crown-6 and dibenzo-21-crown-7 could be synthesized through a three-step protocol starting from salicylaldehyde. Salicylaldehyde was reacted with bis-(2-chloroethyl)ether using K2CO3 in acetonitrile to link the two phenolic groups with the oxyethylene bridge followed by conversion of the formyl group to the hydroxy group via a Baeyer-Villiger reaction and finally linking the two phenolic group with appropriate oxyethylene bridge. The two target crown ethers were obtained in overall yield, 24% and 30%, respectively. This method has a great potential for synthesis of symmetrical as well as unsymmetrical dibenzo crowns with varying oxyethylene bridges. Baeyer-Villiger oxidation could be used to prepare dihydroxy derivative of dibenzo-18-crown-6 through acetylation of dibenzo-18-crown-6 followed by Baeyer-Villiger oxidation. The Baeyer-Villiger oxidation could be substantially accelerated using trifluoroacetic acid.

An Improved Method for Preparing Dibenzo Crown Ethers

In synthesis of symmetrical and unsymmetrical dibenzo crown ethers, the use of dimethyl sulfoxide as a solvent in cyclization allows an increase in the yields, a significant reduction in the reaction time, and simplification of refining.