57165-19-2

Basic information

• Product Name: 9(10H)-Acridinone, 3-methyl-
• Synonyms: 3-Methyl-10H-acridin-9-on;3-methyl-10H-acridin-9-one;3-methylacridin-9(10H)-one;3-methyl-9-acridanone;3-methylacridone
• CAS NO: 57165-19-2
• Molecular Formula: C14H11NO
• Molecular Weight: 209.247
• Mol File: 57165-19-2.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 9(10H)-Acridinone, 3-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 9(10H)-Acridinone, 3-methyl-(57165-19-2)
• EPA Substance Registry System: 9(10H)-Acridinone, 3-methyl-(57165-19-2)

Safety Data

• Hazardous Substances Data: 57165-19-2(Hazardous Substances Data)

Upstream product

• 271-58-9 anthranil 
• 17933-03-8 m-tolylboronic acid 
• 551-93-9 2-aminoacetophenone 
• 23592-52-1 1-<2-<(3-Methylphenyl)amino>phenyl>ethanon 
• 37892-50-5 3-(4-methylphenyl)benzo[c]isoxazole 
• 108-70-3 1,3,5-trichlorobenzene 
• 16524-22-4 2-(m-tolylamino)benzoic acid 

Downstream Products

• 1426677-46-4 3-[(E)-2-phenylethenyl]acridine 

Relevant articles and documents

Access to acridones by tandem copper(i)-catalyzed electrophilic amination/Ag(i)-mediated oxidative annulation of anthranils with arylboronic acids

An efficient and practical approach for the synthesis of medicinally important acridones was developed from anthranils and commercially available arylboronic acids by a tandem copper(i)-catalyzed electrophilic amination/Ag(i)-mediated oxidative annulation strategy. This new and straightforward protocol displayed a broad substrate scope (25 examples) and high functional group tolerance. What's more, a possible mechanistic proposal was also presented.

Copper-catalyzed aerobic oxidative C-H and C-C functionalization of 1-[2-(Arylamino)aryl]ethanones leading to acridone derivatives

Efficient copper-catalyzed aerobic oxidative C-H and C-C functionalization of 1-[2-(arylamino)aryl]ethanones leading to acridones has been developed. The procedure involves cleavage of aromatic C-H and acetyl C-C bonds with intramolecular formation of a diarylketone bond. The protocol uses inexpensive Cu(O2CCF3)2 as catalyst, pyridine as additive, and economical and environmentally friendly oxygen as the oxidant, and the corresponding acridones with various functional groups were obtained in moderate to good yields. Acridone synthesis: Efficient copper-catalyzed aerobic oxidative C-H and C-C functionalization of 1-[2-(arylamino)aryl]ethanones leading to acridones has been developed. The procedure involves cleavage of aromatic C-H and acetyl C-C bonds with intramolecular formation of a diarylketone bond (see scheme). The protocol uses inexpensive Cu(O 2CCF3)2 as catalyst, pyridine as additive, and economical and environmentally friendly oxygen as oxidant. The corresponding acridones with various functional groups were obtained in moderate to good yields. Copyright

An In-depth Study of the Azidobenzophenone-Anthranil-Acridone Transformation

The title transformation, particularly the conversion of anthranils into acridones, is shown to be critically sensitive to temperature, solvent, substituent, and metal catalysts.Thus the conversion of 3-(p-tolyl)anthranil into an acridone gives a ratio of 2-and 3-methyl derivatives varying from 0.6:1 to 4.7:1 with changing temperature and solvent.In other similar thermolyses, solvents (e.g. 1,2,4-trichlorobenzene) were incorporated into the product and traces of metals and their derivatives had a dramatic effect on the rate and course of the reaction.The most effective catalysts were iron powder and aluminium acetylacetonate. 3-(2,6-Disubstituted phenyl)anthranils gave acridones in which the substituents were either lost or rearranged onto N or C, the last cases involving sequential -sigmatropic shifts. 3-Thienylanthranils gave related thienoquinolones on thermolysis; again the reaction were very sensitive to catalysis.Blocked thienylanthranils also gave rearrangement products, but the non-aromatic intermediates could be isolated.