5472-23-1

Basic information

• Product Name: NSC27927
• Synonyms: NSC27927;10-Phenyl-9(10H)-acridinone;10-Phenyl-9(10H)-acridone;Phenylacridone;10-phenylacridin-9-one;10-Phenyl-9(10H)-acridinone 95%;10-Phenyl-9(10;10-Phenylacridone
• CAS NO: 5472-23-1
• Molecular Formula: C₁₉H₁₃NO
• Molecular Weight: 271.3126
• EINECS: 200-258-5
• Mol File: 5472-23-1.mol
• Article Data: 36

Chemical Properties

• Melting Point: 274-279°C
• Boiling Point: 428.1°C at 760 mmHg
• Flash Point: 169.6°C
• Appearance: /
• Density: 1.245g/cm³
• Vapor Pressure: 1.56E-07mmHg at 25°C
• Refractive Index: 1.676
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -5.61±0.20(Predicted)
• CAS DataBase Reference: NSC27927(CAS DataBase Reference)
• NIST Chemistry Reference: NSC27927(5472-23-1)
• EPA Substance Registry System: NSC27927(5472-23-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 5472-23-1(Hazardous Substances Data)

Usage

Uses

Substrate was reported in the synthesis of oxirane derivatives through a two-step synthesis involving a McMurray reaction with 2-Adamantanone.

InChI:InChI=1/C19H13NO/c21-19-15-10-4-6-12-17(15)20(14-8-2-1-3-9-14)18-13-7-5-11-16(18)19/h1-13H

Upstream product

• 188296-78-8 N-Phenyl-1,2,3,4-tetrahydroacridin-9-one 
• 17626-44-7 2-(N,N-diphenylamino)benzoic acid 
• 108-00-9 N,N-dimethylethylenediamine 
• 209412-76-0 [1-(2-Diphenylamino-phenyl)-meth-(E)-ylideneaminooxy]-ethaneperoxoic acid tert-butyl ester 
• 206645-82-1 10-phenyldispiro(acridine-9(10H),3'-[1,2]dioxetane-4',2''-tricyclo[3.3.1.1^3,7]decane) 
• 35708-19-1 Methyl N-phenylanthranilate 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 591-50-4 iodobenzene 
• 91-40-7 2-(phenylamino)benzoic acid 
• 62-53-3 aniline 
• 88-65-3 2-bromobenzoic-acid 
• 1747-80-4 2-fluoro-N-phenylbenzamide 
• 930-21-2 2-azetidinone 
• 4295-36-7 2,3-dihydroquinolin-4(1H)-one 

Downstream Products

• 108139-68-0 9-chloro-10-phenyl-acridinium; chloride 
• 113493-31-5 4-(9-methoxy-10-phenyl-9,10-dihydro-acridin-9-yl)-N,N-dimethyl-aniline 
• 151237-25-1 10,10'-diphenyl-9,9'(10H,10'H)-biacridinylidene 
• 192184-77-3 9,10-dihydro-10-phenyl-9-(tricyclo[3.3.1.1^3,7]decylidene)acridine 
• 10336-24-0 10-phenyl-9,10-dihydroacridine 
• 78943-59-6 N-phenyldibenzazepine 

Relevant articles and documents

Boron trifluoride etherate promoted microwave-assisted synthesis of antimalarial acridones

A microwave-assisted, rapid and efficient method using boron trifluoride etherate (BF3.Et2O) for the synthesis of acridones, via an intramolecular acylation of N-phenylanthranilic acid derivatives, has been developed. The reaction proceeds under solvent-free conditions, tolerates a wide range of functional groups, and provides rapid access to a range of acridones in good to excellent yields. Several of the synthesized acridones exhibited potent antimalarial activities against CQ sensitive and multi-drug resistant (MDR) parasites.

Acridine compound and light-emitting device

The invention relates to an acridine compound and an application thereof. The structural formula of the acridine compound is shown as a formula (I), wherein Ar is selected from substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, R1 and R2 are respectively and independently selected from H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, R1 and R2 are respectively and independently selected from H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, and x is selected from oxygen or sulfur. The acridine compound provided by the invention has good electron transport performance and hole transport performance, so that the acridine compound can be used as a material of a hole transport layer and an electron transport layer, due to the fact that the acridine compound has a high triplet state energy level, the acridine compound becomes a good bipolar main body material, the acridine compound is used as the main body material of a light-emitting layer, more exciton energy can be transmitted to a light-emitting body, and the light-emittingefficiency of a light-emitting device is improved.

2-Aminobenzaldehyde, a common precursor to acridines and acridones endowed with bioactivities

By starting from a common substrate, 2-aminobenzaldehyde, both acridines and acridones were prepared. The former were generated in high yields by copper-catalyzed N-arylation followed by acid-mediated cyclization while the latter were obtained by double copper-catalyzed N-arylation followed by cyclization under the same reaction conditions. Moreover, acridine was subjected to deprotometalation by recourse to a lithium-zinc base and converted to the corresponding 4-iodo derivative, which was involved in copper-catalyzed couplings with pyrrolidinone and pyrazole. Finally, addition of pyrazole, indole and carbazole onto the 9 position of bare acridine was improved. While moderate biological activity was noticed in melanoma cells growth inhibition, the newly prepared compounds feature interesting photophysical properties which were evaluated in a preliminary study.