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

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

Uses

Used in Organic Synthesis:
2,4-Dihydroxy-3-phenylquinoline is used as a building block in organic synthesis for the creation of various types of drugs and pharmaceuticals. Its unique structure and functional groups contribute to the development of new chemical entities with potential therapeutic applications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 2,4-Dihydroxy-3-phenylquinoline is utilized as a key intermediate for the synthesis of pharmaceuticals. Its presence in the molecular structure can enhance the pharmacological properties of the final drug products.
Used in Antioxidant Applications:
2,4-Dihydroxy-3-phenylquinoline is studied for its potential antioxidant properties, which can help protect cells from oxidative stress and damage. This makes it a promising candidate for the development of antioxidants in various industries, including pharmaceuticals and cosmetics.
Used in Anti-inflammatory Applications:
2,4-Dihydroxy-3-phenylquinoline has also been investigated for its anti-inflammatory properties, which can be beneficial in the treatment of various inflammatory conditions. Its potential use in anti-inflammatory drugs can provide relief to patients suffering from chronic inflammation.
Used in Anti-cancer Applications:
2,4-Dihydroxy-3-phenylquinoline has been studied for its potential anti-cancer properties, making it a candidate for the development of novel cancer therapeutics. Its ability to target and inhibit cancer cells can contribute to the advancement of cancer treatment options.
Used in Research and Development:
Due to its unique structure and functional groups, 2,4-Dihydroxy-3-phenylquinoline is a valuable compound in research and development. It can be used to explore new chemical reactions, synthesize novel compounds, and investigate its pharmacological activities in various fields of science.

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

• 118-92-3 anthranilic acid 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 103-81-1 Benzeneacetamide 
• 556-89-8 nitrourea 
• 477950-06-4 3-benzylamino-3-phenylquinoline-2,3(1H,3H)-dione 
• 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 
• 62-53-3 aniline 
• 83-13-6 diethyl 2-phenylmalonate 
• 536-74-3 phenylacetylene 
• 615-43-0 2-iodophenylamine 
• 103-80-0 phenylacetyl chloride 

Downstream Products

• 72004-74-1 4-amino-3-phenylquinoline-2<1H>-one 
• 83609-71-6 6-Phenyl-dibenzo<1,6>naphthyridin-11(12H)-on 
• 28565-95-9 3-hydroxy-3-phenylquinoline-2,4(1H,3H)-dione 
• 108832-15-1 2,4-dichloro-3-phenylquinoline 
• 144603-13-4 3-bromo-3-phenylquinoline-2,4(1H,3H)-dione 
• 108832-06-0 3-Phenyl-4-tosyloxy-2(1H)-chinolon 
• 144603-32-7 3-chloro-3-phenylquinoline-2,4(1H,3H)-dione 
• 108832-11-7 4-Azido-2-chloro-3-phenylquinoline 
• 157027-42-4 5-Chloro-4-phenyl-1,2,3,9b-tetraaza-cyclopenta[a]naphthalene 
• 157027-53-7 4-chloro-3-phenyl-2-(triphenylphosphoranylideneamino)-quinoline 
• 157027-51-5 C₃₃H₂₄ClN₂P 
• 1432733-36-2 1,2-dihydro-2-oxo-3-phenylquinolin-4-yl dihydrogen phosphate 
• 58980-12-4 2-{[oxo(phenyl)acetyl]amino}benzoic acid 

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

Synthesis of Benzofuranes by Cyclodehydrogenation of Phenylmalonyl Heterocyclic Compounds

Phenylmalonyl heterocyclic compounds such as the quinolones 1a-c or 3, benzoquinolizinones 6a, b and the phenalenones 8a, b can be converted to benzofuranes (2a-c, 7a, b and 9a, b) by cyclodehydrogenation with Pd/C in boiling diphenyl ether. 2-Phenylchinc

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

One-step Synthesis of 3-Unsubstituted 4-Hydroxy-2(1H)-Quinoline

3-Unsubstituted 4-hydroxy-2(1H)-quinolone (DHQ) derivatives were synthesized from aniline derivatives and diethyl malonate at low temperature using AlCl3 as catalyst and Eaton reagent as acidic environment. A reaction mechanism was proposed and elucidated. Different synthetic intermediates are specially prepared or purified and used to understand the reaction and validation mechanism.

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

Incorporation of carbon dioxide into molecules of acetylene hydrocarbons on heterogeneous Ag-containing catalysts

The reaction between 2-(2-phenylethynyl)aniline and carbon dioxide on heterogeneous Ag-containing catalysts can lead either to benzoxazine-2-one or to 4-hydroxyquinoline-2(1Н)-one, depending on the reaction conditions (nature of the base, CO2 p

Cu(i)-catalyzed chemical fixation of CO2 with 2-alkynylaniline into 4-hydroxyquinolin-2(1H)-one

A copper(i) catalyzed reaction of 2-alkynylaniline with CO2 using DBU as base to produce 4-hydroxyquinolin-2(1H)-one derivatives in moderate to good yield is presented. In this reaction, a unique bond cleavage pattern for CO2 was observed that one of the C-O double bonds of CO 2 was totally broken and rearranged into two moieties in the absence of the reductive reagent. This efficient reaction system showed the wide generality of substrates including nitro, bromo, cyano and methoxylcarbonyl groups. A possible mechanism containing isocyanate intermediate is proposed. This journal is the Partner Organisations 2014.

Oxidative ring opening of 3-hydroxyquinoline-2,4(1H,3H)-diones into N-(α-ketoacyl)anthranilic acids Dedicated to Professor Slovenko Polanc on his 65th birthday

N-(α-Ketoacyl)anthranilic acids were prepared by oxidative ring opening of 3-hydroxyquinoline-2,4(1H,3H)-diones by using paraperiodic acid (H5IO6) or sodium periodate (NaIO4). The optimisation of the reaction conditions is

Efficient preparation of 4-hydroxyquinolin-2(1 H)-one derivatives with silver-catalyzed carbon dioxide incorporation and intramolecular rearrangement

Although 4-hydroxyquinolin-2(1H)-one derivatives have attracted much attention due to their biological benefits, conventional reactions under harsh heat conditions must be employed to provide these key compounds. In the presence of a catalytic amount of s