20953-66-6

Basic information

• Product Name: 9-(4-chlorophenyl)acridine
• Synonyms: acridine, 9-(4-chlorophenyl)-
• CAS NO: 20953-66-6
• Molecular Formula: C₁₉H₁₂ClN
• Molecular Weight: 289.7583
• Mol File: 20953-66-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 435.1°C at 760 mmHg
• Flash Point: 249.5°C
• Density: 1.27g/cm³
• Vapor Pressure: 2.29E-07mmHg at 25°C
• Refractive Index: 1.713
• CAS DataBase Reference: 9-(4-chlorophenyl)acridine(CAS DataBase Reference)
• NIST Chemistry Reference: 9-(4-chlorophenyl)acridine(20953-66-6)
• EPA Substance Registry System: 9-(4-chlorophenyl)acridine(20953-66-6)

Safety Data

• Hazardous Substances Data: 20953-66-6(Hazardous Substances Data)

Upstream product

• 122-39-4 diphenylamine 
• 74-11-3 para-chlorobenzoic acid 
• 4357-57-7 9-bromoacridine 
• 1679-18-1 4-Chlorophenylboronic acid 
• 2894-51-1 2-amino-4'-chlorobenzophenone 
• 108-94-1 cyclohexanone 
• 1207-69-8 9-Chloroacridine 
• 17583-00-5 2-phenylaminobenzonitrile 

Relevant articles and documents

Pd-Catalyzed Approach for Assembling 9-Arylacridines via a Cascade Tandem Reaction of 2-(Arylamino)benzonitrile with Arylboronic Acids in Water

A novel palladium-catalyzed protocol for the synthesis of 9-arylacridines via tandem reaction of 2-(arylamino)benzonitrile with arylboronic acids in water has been developed with good functional group tolerance. The present synthetic route could be readily scaled up to gram quantity without difficulty. This methodology was further extended to the synthesis of a 4′-OH derivative, which showed estrogenic biological activity. Preliminary mechanistic experiments showed that this transformation involves a nucleophilic addition of aryl palladium species to the nitrile to generate an aryl ketone intermediate followed by an intramolecular Friedel-Crafts acylation and dehydration to acridines.

Synthesis of Substituted Acridines through a Palladium-Catalyzed Condensation/Cyclization/Tautomerization Sequence

Herein, we report an efficient strategy for the synthesis of 9-aryl-substituted acridines from cyclohexanones and 2-aminobenzophenones in the presence of a palladium catalyst. Molecular oxygen is applied as a green oxidant. Various cyclohexanones acted as the aryl source to construct the nitrogen-containing heterocycles through a condensation/cyclization/tautomerization sequence.

Structural studies on bioactive compounds. Part 33. Synthesis of 9- arylacridines by palladium-mediated couplings

9-Halogenoacridines undergo Suzuki cross-coupling reactions with a range of arylboronic and thienyl-3-boronic acids to yield substituted 9- arylacridines and 9-(thien-3-yl)acridines.