102594-26-3

Basic information

• Product Name: 1,3-dibenzyl-2-hydroxyquinolin-4(1H)-one
• CAS NO: 102594-26-3
• Molecular Formula: C₂₃H₁₉NO₂
• Molecular Weight: 341.4025
• Mol File: 102594-26-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 521.4°C at 760 mmHg
• Flash Point: 269.2°C
• Density: 1.28g/cm³
• Vapor Pressure: 1.06E-11mmHg at 25°C
• Refractive Index: 1.687
• CAS DataBase Reference: 1,3-dibenzyl-2-hydroxyquinolin-4(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-dibenzyl-2-hydroxyquinolin-4(1H)-one(102594-26-3)
• EPA Substance Registry System: 1,3-dibenzyl-2-hydroxyquinolin-4(1H)-one(102594-26-3)

Safety Data

• Hazardous Substances Data: 102594-26-3(Hazardous Substances Data)

Upstream product

• 758640-21-0 N-Benzylaniline 
• 607-81-8 diethyl 2-benzylmalonate 
• 552-16-9 ortho-nitrobenzoic acid 
• 100-52-7 benzaldehyde 
• 501-52-0 3-Phenylpropionic acid 

Downstream Products

• 369651-55-8 1,3-dibenzyl-3-hydroxy-2,4(1H,3H)-quinolinedione 
• 35887-49-1 1,3-dibenzyl-3-hydroxy-1,3-dihydro-2H-indol-2-one 
• 144619-45-4 1,3-Dibenzyl-3-chloro-1H-quinoline-2,4-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.

Halogenation Reactions in Position 3 of Quinoline-2,4-dione Systems by Electrophilic Substitution and Halogen Exchange

3-Substituted 4-hydroxy-2(1H)-quinolones 3, 5, 7 are halogenated with bromine or sulfuryl chloride to yield the quinolinediones 9 or 10.Reactions of 3, 5, 7 with chloroform gives the dichloromethyl quinolinediones 11.Halogen exchange leads from the chloro quinolinediones 10 to fluoro quinolinedones 12 and to azido quinolinediones 13.Similarly the dichloro quinolinediones 10an reacts to the difluoro quinolinedione 14, which is reduced to the 3-fluoro-4-hydroxyquinolone 16 and reacts again with sulfuryl chloride to give the mixed 3-chloro-3-fluoroquinolinedione 15.Keywords.Fluorination; 4-Hydroxy-2(1H)-quinolones, 3-alkyl/3-aryl/3-fluoro; 1-Hydroxy-benzoquinolizine-3-ones, 2-alkyl/3-aryl; Quinoline-2,4(1H,3H)-diones, 3-azido-3-alkyl/3-aryl, 3-bromo-3-alkyl/3-aryl, 3-chloro-3-alkyl/3-aryl, 3-fluoro-3-alkyl/3-aryl, 3-dichloromethyl-3-alkyl/3-aryl, 3-chloro-3-fluoro.