28563-21-5

Basic information

• Product Name: 2-hydroxy-6-methoxy-3-phenylquinolin-4(1H)-one
• Synonyms: 4-hydroxy-6-methoxy-3-phenyl-1,2-dihydroquinolin-2-one
• CAS NO: 28563-21-5
• Molecular Formula: C₁₆H₁₃NO₃
• Molecular Weight: 267.2793
• Mol File: 28563-21-5.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 459.1°C at 760 mmHg
• Flash Point: 231.4°C
• Density: 1.315g/cm³
• Vapor Pressure: 3.19E-09mmHg at 25°C
• Refractive Index: 1.65
• CAS DataBase Reference: 2-hydroxy-6-methoxy-3-phenylquinolin-4(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-hydroxy-6-methoxy-3-phenylquinolin-4(1H)-one(28563-21-5)
• EPA Substance Registry System: 2-hydroxy-6-methoxy-3-phenylquinolin-4(1H)-one(28563-21-5)

Safety Data

• Hazardous Substances Data: 28563-21-5(Hazardous Substances Data)

Upstream product

• 1227736-32-4 3-phenyl-6-methoxy-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)quinolin-2(1H)-one 
• 104-94-9 4-methoxy-aniline 
• 83-13-6 diethyl 2-phenylmalonate 

Downstream Products

• 144603-48-5 3-Chloro-6-methoxy-3-phenyl-1H-quinoline-2,4-dione 
• 144603-17-8 3-bromo-6-methoxy-3-phenylquinoline-2,4(1H,3H)-dione 
• 1227736-32-4 3-phenyl-6-methoxy-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)quinolin-2(1H)-one 
• 685893-24-7 2,4-dichloro-6-methoxy-3-phenylquinoline 
• 1286131-48-3 4-chloro-6-methoxy-3-phenylquinolin-2(1H)-one 
• 1286950-68-2 4-chloro-6-methoxy-3-phenylquinolin-2(1H)-one 
• 28566-01-0 4,6-dihydroxy-3-phenylquinolin-2(1H)-one 
• 1303613-90-2 3-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)-6-methoxy-3-phenylquinoline-2,4(1H,3H)-dione 
• 1303613-89-9 6-methoxy-3-phenyl-3-(4-phenyl-1H-1,2,3-triazol-1-yl)quinoline-2,4(1H,3H)-dione 

Relevant articles and documents

Design, synthesis and antitubercular potency of 4-hydroxyquinolin-2(1H)-ones

In this study, a 50-membered library of substituted 4-hydroxyquinolin-2(1H)-ones and two closely related analogues was designed, scored in-silico for drug likeness and subsequently synthesized. Thirteen derivatives, all sharing a common 3-phenyl substituent showed minimal inhibitory concentrations against Mycobacterium tuberculosis H37Ra below 10 μM and against Mycobacterium bovis AN5A below 15 μM but were inactive against faster growing mycobacterial species. None of these selected derivatives showed significant acute toxicity against MRC-5 cells or early signs of genotoxicity in the Vitotox assay at the active concentration range. The structure activity study relation provided some insight in the further favourable substitution pattern at the 4-hydroxyquinolin-2(1H)-one scaffold and finally 6-fluoro-4-hydroxy-3-phenylquinolin-2(1H)-one (38) was selected as the most promising member of the library with a MIC of 3.2 μM and a CC50 against MRC-5 of 67.4 μM.

Copper(I)-catalyzed [3+2] cycloaddition of 3-azidoquinoline-2,4(1H,3H)- diones with terminal alkynes

3-Azidoquinoline-2,4(1H,3H)-diones 1,which are readily available from 4-hydroxyquinolin-2(1H)-ones 4 via 3-chloroquinoline-2,4(1H,3H)-diones 5, afford, in copper(I)-catalyzed [3+2] cycloaddition reaction with terminal acetylenes, 1,4-disubstituted 1,2,3-t

Rapid microwave-enhanced synthesis of 4-hydroxyquinolinones under solvent-free conditions

3-Aryl-4-hydroxyquinolin-2(1H)-ones are potent and selective glycine-site NMDA receptor antagonists of pharmaceutical interest. A novel microwave-enhanced synthesis of such quinolinones under solvent-free conditions has been developed. The quinolinones ar