14933-29-0

Basic information

• Product Name: 2,4-Dihydroxy-3-phenylquinoline
• Synonyms: 2,4-Dihydroxy-3-phenylquinoline
• CAS NO: 14933-29-0
• Molecular Formula: C₁₅H₁₁NO₂
• Molecular Weight: 237.25334
• Mol File: 14933-29-0.mol
• Article Data: 27

Chemical Properties

• Melting Point: 318 °C
• Boiling Point: 411.8°Cat760mmHg
• Flash Point: 202.8°C
• Appearance: /
• Density: 1.323g/cm³
• Vapor Pressure: 1.62E-07mmHg at 25°C
• Refractive Index: 1.677
• PKA: 4.50±1.00(Predicted)
• CAS DataBase Reference: 2,4-Dihydroxy-3-phenylquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dihydroxy-3-phenylquinoline(14933-29-0)
• EPA Substance Registry System: 2,4-Dihydroxy-3-phenylquinoline(14933-29-0)

Safety Data

• Hazardous Substances Data: 14933-29-0(Hazardous Substances Data)

Usage

General Description

2,4-Dihydroxy-3-phenylquinoline is a chemical compound with the molecular formula C15H11NO2. It is a quinoline derivative with two hydroxyl groups and a phenyl ring. 2,4-Dihydroxy-3-phenylquinoline is used in organic synthesis and medicinal chemistry as a building block for the synthesis of various types of drugs and pharmaceuticals. It has also been studied for its potential pharmacological activities, including antioxidant, anti-inflammatory, and anti-cancer properties. Its unique structure and functional groups make it a versatile compound with potential applications in various fields of research and industry.

InChI:InChI=1/C15H11NO2/c17-14-11-8-4-5-9-12(11)16-15(18)13(14)10-6-2-1-3-7-10/h1-9H,(H2,16,17,18)

Upstream product

• 28565-98-2 N-phenylacetylanthranilic acid 
• 556-89-8 nitrourea 
• 477950-06-4 3-benzylamino-3-phenylquinoline-2,3(1H,3H)-dione 
• 15781-73-4 di(2,4,6-trichlorophenyl)-2-phenylmalonate 
• 62-53-3 aniline 
• 83-13-6 diethyl 2-phenylmalonate 
• 773837-37-9 sodium cyanide 
• 144603-32-7 3-chloro-3-phenylquinoline-2,4(1H,3H)-dione 
• 124-38-9 carbon dioxide 
• 13141-38-3 2-phenylethynylaniline 
• 536-74-3 phenylacetylene 
• 615-43-0 2-iodophenylamine 
• 103-80-0 phenylacetyl chloride 
• 134-20-3 2-carbomethoxyaniline 

Downstream Products

• 108832-15-1 2,4-dichloro-3-phenylquinoline 
• 91622-62-7 4-Phenylamino-3-phenyl-chinolin-2(1H)-on 
• 83619-97-0 4-Benzylamino-3-phenyl-chinolin-2(1H)-on 
• 622404-76-6 2-oxo-2,3-dihydro-1H-indol-3-yl benzoate 
• 1432733-36-2 1,2-dihydro-2-oxo-3-phenylquinolin-4-yl dihydrogen phosphate 
• 58980-12-4 2-{[oxo(phenyl)acetyl]amino}benzoic acid 
• 129-24-8 4-phenyl-3-hydroxyquinolin-2(1H)-one 
• 1447565-22-1 2,3-diphenyl-2',4'-dihydro-1'H-spiro[indene-1,3'-quinoline]-2',4'-dione 

Relevant articles and documents

Reaction of 3-aminoquinoline-2,4-diones with nitrourea. Synthetic route to novel 3-ureidoquinoline-2,4-diones and imidazo[4,5-c]quinoline-2,4-diones

1-Unsubstituted 3-alkyl/aryl-3-amino-1H,3H-quinoline-2,4-diones react with 1-substituted and 1,1-disubstituted ureas in boiling acetic acid to give 2,6-dihydro-imidazo[1,5-c]quinazoline-3,5-diones. In contrast, the reaction of these amines with nitrourea in dioxane affords novel 3-alkyl/aryl-3-ureido-1H, 3H-quinoline-2,4-diones or 9b-hydroxy-3a-alkyl/aryl-3,3a,5,9b-tetrahydro-1H- imidazo[4,5-c]quinoline-2,4-diones, which can smoothly be dehydrated to 3a-alkyl/aryl-3,3a-dihydro-5H-imidazo[4,5-c]quinoline-2,4-diones. All three types of products can be converted to 2,6-dihydro-imidazo[1,5-c]quinazoline-3,5- diones by refluxing in acetic acid. Graphical Abstract

Reaction of Tertiary 2-Chloroketones with Cyanide Ions: Application to 3-Chloroquinolinediones

3-Chloroquinoline-2,4-diones react with cyanide ions in dimethyl formamide to give 3-cyanoquinoline-2,4-diones in small yields due to the strong hindrance of the substituent at the C-3 atom. Good yields can be achieved if the substituent at this position

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.

Structure activity relationships of 4-hydroxy-2-pyridones: A novel class of antituberculosis agents

Pyridone 1 was identified from a high-throughput cell-based phenotypic screen against Mycobacterium tuberculosis (Mtb) including multi-drug resistant tuberculosis (MDR-TB) as a novel anti-TB agent and subsequently optimized series using cell-based Mtb ass