Dibenzo-18-crown-6

Base Information

• Chemical Name: Dibenzo-18-crown-6
• CAS No.: 14187-32-7
• Deprecated CAS: 54765-16-1,63172-39-4,66105-26-8,73128-69-5,63172-39-4,66105-26-8,73128-69-5
• Molecular Formula: C20H24O6
• Molecular Weight: 360.407
• Hs Code.: 29329995
• European Community (EC) Number: 238-041-3
• NSC Number: 147771
• UNII: 0A7W45JCS9
• DSSTox Substance ID: DTXSID6022428
• Nikkaji Number: J14.747H
• Wikipedia: Dibenzo-18-crown-6
• Wikidata: Q5272256
• Metabolomics Workbench ID: 52751
• ChEMBL ID: CHEMBL345536
• Mol file: 14187-32-7.mol

Synonyms:dibenzo-18-crown-6;polyether XXVIII

Chemical Property of Dibenzo-18-crown-6

Chemical Property:

• Appearance/Colour: white to slightly beige fluffy powder
• Vapor Pressure: 3.65E-10mmHg at 25°C
• Melting Point: 162-164 °C(lit.)
• Refractive Index: 1.5
• Boiling Point: 503.1 °C at 760 mmHg
• Flash Point: 206 °C
• PSA: 55.38000
• Density: 1.108 g/cm³
• LogP: 2.94880
• Storage Temp.: Store below +30°C.
• Sensitive.: air sensitive
• Solubility.: 0.007g/l
• Water Solubility.: sparingly soluble
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 360.15728848
• Heavy Atom Count: 26
• Complexity: 300

Purity/Quality:

99.0% min ^*data from raw suppliers

Dibenzo-18-crown-6 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36-36/37/38-20/21/22
• Safety Statements: 26-37/39-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Other Organic Compounds
• Canonical SMILES: C1COC2=CC=CC=C2OCCOCCOC3=CC=CC=C3OCCO1
• General Description: Dibenzo-18-crown-6 (DBC) is a crown ether derivative that serves as a phase transfer catalyst in organic synthesis, facilitating reactions such as the formation of selenides and phenyl-1,2-dielenole in three-phase catalytic systems. Additionally, its derivatives, including benzothiazole, crown o-aminoketones, quinazolines, and quinones, have been synthesized and evaluated for antiviral activity. While some derivatives exhibited moderate or low activity against viruses like variola vaccine virus and herpes simplex virus, others showed no significant antiviral effects. DBC's versatility in both catalytic and medicinal applications highlights its importance in chemical and pharmaceutical research.

Technology Process of Dibenzo-18-crown-6

There total 15 articles about Dibenzo-18-crown-6 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) + 3-oxa-1,5-dichloropentane (111-44-4) → dibenzo-18-crown-6 (14187-32-7)

Guidance literature:

With potassium hydroxide; In dimethyl sulfoxide; for 0.0833333h; Microwave irradiation;

DOI:10.2174/15701786113106660075

Reference yield: 73.0%

bis(2-hydroxyphenoxyethyl)ether (23116-94-1) + 3-oxa-1,5-dichloropentane (111-44-4) → dibenzo-18-crown-6 (14187-32-7)

Guidance literature:

With potassium hydroxide; In dimethyl sulfoxide; for 0.0833333h; Microwave irradiation;

DOI:10.2174/15701786113106660075

Reference yield: 55.0%

benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) + 3-oxa-1,5-dichloropentane (111-44-4) → dibenzo-18-crown-6 (14187-32-7) + 1,2-bis[2'-(2''-chloroethoxy)ethoxy]benzene (41758-00-3) + 2-(5-chloro-3-oxa-1-pentyloxy)phenol (111875-63-9)

Guidance literature:

With potassium hydroxide; In dimethyl sulfoxide; at 90 ℃; for 2.5h; Yields of byproduct given;

upstream raw materials:

bis(2-hydroxyphenoxyethyl)ether

3-oxa-1,5-dichloropentane

benzene-1,2-diol

salicylaldehyde

Refernces

REACTIONS OF SELENIUM AND TELLURIUM METALS WITH PHENYLACETYLENE IN THREE-PHASE CATALYTICAL SYSTEMS

10.1016/S0040-4039(00)95269-9

The research aimed to investigate the reactions of selenium and tellurium metals with phenylacetylene in three-phase catalytic systems, utilizing phase transfer techniques in organic synthesis. The study proposed a radical anion chain mechanism for the reaction involving tellurium metal and phenylacetylene, leading to the formation of phenyl-1,2-dielenole (compound 2) with a 20% yield. The researchers also extended their findings to the synthesis of selenides (compounds 2a-d) by trapping the intermediate anion 2 with alkyl halides, yielding selenides in 40-50% yield. Key chemicals used in the process included selenium and tellurium metals, phenylacetylene, alkyl halides (such as methyl, ethyl, isopropyl, and butyl halides), aqueous base (potassium hydroxide), and phase transfer catalysts like dibenzo-18-crown-6. The study concluded that the addition of reducing agents could initiate the reaction of tellurium metal with phenylacetylene, and the use of hydrazine hydrate medium could elevate the yields of the synthesized compounds.

SYNTHESIS AND ANTIVIRAL ACTIVITY OF DERIVATIVES OF DIBENZO-18-CROWN-6

10.1007/BF00763530

The study investigates the synthesis and antiviral activity of derivatives of dibenzo-18-crown-6 (DBC). The researchers used starting materials such as syn-2,14-diamino- and anti-2,13-diaminodibenzo-18-crown-6 (la, b) and unsubstituted DBC. They synthesized various derivatives, including benzothiazole derivatives (lla, b) by reacting (la) and (Ib) with dithiocyanogen in acetic acid, crown o-aminoketones (llI) and (IV) by reacting the diamines with benzoyl chlorides under Friedel-Crafts conditions, quinazolines (V) by boiling the aminoketones in formamide, and a quinone (VI) by condensing DBC with imidazo-4,5-dicarboxylic acid in polyphosphoric acid. The structures of the products were confirmed by IR and UV spectra, elemental analysis, and mass spectrometry. The antiviral activity of these compounds was tested against various viruses, including variola vaccine virus (VVV), herpes simplex virus (HSV), classical avian plague virus (CAPV), Newcastel disease virus (NDV), vesicular stomatitis virus (VSV), Venezuelan equine encephalomyelitis virus (VEEN), and ECHO-6. The results showed that some of the compounds exhibited moderate or low antiviral activity against certain viruses, while others did not show significant antiviral activity.