26386-86-7

Basic information

• Product Name: 3-Hydroxyquinolin-2-one
• Synonyms: 3-Hydroxyquinolin-2-one;3-HYDROXYQUINOLIN-4-ONE;3-HYDROXYQUINOLIN-2(1H)-ONE
• CAS NO: 26386-86-7
• Molecular Formula: C₉H₇NO₂
• Molecular Weight: 161.15738
• Mol File: 26386-86-7.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 427.4°C at 760 mmHg
• Flash Point: 212.3°C
• Appearance: /
• Density: 1.376g/cm³
• Vapor Pressure: 4.58E-08mmHg at 25°C
• Refractive Index: 1.657
• CAS DataBase Reference: 3-Hydroxyquinolin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Hydroxyquinolin-2-one(26386-86-7)
• EPA Substance Registry System: 3-Hydroxyquinolin-2-one(26386-86-7)

Safety Data

• Hazardous Substances Data: 26386-86-7(Hazardous Substances Data)

Usage

General Description

3-Hydroxyquinolin-2-one, also known as 3-hydroxy-2-quinolinone or 2-hydroxyquinolin-3(2H)one, is a chemical compound that belongs to the quinolinone class of organic compounds. It is a derivative of quinoline and has a hydroxy group at the 3-position. 3-Hydroxyquinolin-2-one has been found to have various biological and pharmacological activities, including antioxidant, anticancer, and antimicrobial properties. It has also been researched for its potential as a chelating agent for metal ions and as a precursor for the synthesis of heterocyclic compounds. 3-Hydroxyquinolin-2-one has shown promise in various biological and medical applications, making it an important compound in the field of medicinal chemistry and drug discovery.

InChI:InChI=1/C9H7NO2/c11-8-5-6-3-1-2-4-7(6)10-9(8)12/h1-5,11H,(H,10,12)

Upstream product

• 186581-53-3 diazomethane 
• 91-56-5 indole-2,3-dione 
• 13493-47-5 N-(2-formylphenyl)acetamide 
• 7218-25-9 1-(Chloroacetyl)-1H-indole-2,3-dione 
• 7732-18-5 water 
• 24186-92-3 3-methoxyquinolin-2(1H)-one 
• 6141-22-6 2-chloro-N-(2-formylphenyl)acetamide 
• 90785-84-5 4-carboxy-3-methoxyquinolin-2(1H)-one 
• 128676-94-8 3-hydroxy-2-chloroquinoline 
• 98192-27-9 5,6,5',6'-tetrahydroxy-2,2'-biindolyl 
• 91587-89-2 3-hydroxy-2-oxoquinoline-4-carboxylic acid 
• 612-62-4 2-Chloroquinoline 
• 21267-23-2 ethyl diazo(3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)acetate 
• 93002-02-9 ethyl 3-hydroxy-2-oxo-1,2-dihydro-quinoline-4-carboxylate 

Downstream Products

• 85163-74-2 3-[3-(1-Cyclohexyl-1H-tetrazol-5-yl)-propoxy]-1H-quinolin-2-one 
• 85163-73-1 N-Cyclohexyl-N-ethyl-4-(2-oxo-1,2-dihydro-quinolin-3-yloxy)-butyramide 
• 137793-17-0 3-Hydroxy-4-(trans-2-iodocyclohexyl)-1-methylquinolin-2(1H)-one 
• 135926-39-5 1-phenyl-8-fluoro-3-methyl-2(1H)-quinolone 
• 1443547-25-8 3-(but-3-en-1-yl)oxyquinolin-2(1H)-one 
• 1434103-17-9 4-(4-fluorophenyl)-3-hydroxyquinolin-2(1H)-one 
• 129-24-8 4-phenyl-3-hydroxyquinolin-2(1H)-one 
• 24186-98-9 3-hydroxy-4-methylquinolin-2(1H)-one 
• 1374108-51-6 C₁₉H₁₈FNO₃ 
• 1374108-52-7 C₂₀H₁₇F₄NO₅S 
• 1374108-53-8 C₂₉H₃₁FN₂O₂ 
• 1374107-19-3 2-(4-diethylaminophenyl)-3-(1-(fluoromethyl)-2-hydroxyethoxy)quinoline 
• 1436432-55-1 3-hydroxy-4-p-tolylquinolin-2(1H)-one 

Relevant articles and documents

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Enantioselective Intermolecular Excited-State Photoreactions Using a Chiral Ir Triplet Sensitizer: Separating Association from Energy Transfer in Asymmetric Photocatalysis

Enantioselective catalysis of excited-state photoreactions remains a substantial challenge in synthetic chemistry, and intermolecular photoreactions have proven especially difficult to conduct in a stereocontrolled fashion. Herein, we report a highly enantioselective intermolecular [2 + 2] cycloaddition of 3-alkoxyquinolones catalyzed by a chiral hydrogen-bonding iridium photosensitizer. Enantioselectivities as high as 99% ee were measured in reactions with a range of maleimides and other electron-deficient alkene reaction partners. An array of kinetic, spectroscopic, and computational studies supports a mechanism in which the photocatalyst and quinolone form a hydrogen-bonded complex to control selectivity, yet upon photoexcitation of this complex, energy transfer sensitization of maleimide is preferred. The sensitized maleimide then reacts with the hydrogen-bonded quinolone-photocatalyst complex to afford a highly enantioenriched cycloadduct. This finding contradicts a long-standing tenet of enantioselective photochemistry that held that stereoselective photoreactions require strong preassociation to the sensitized substrate in order to overcome the short lifetimes of electronically excited organic molecules. This system therefore suggests that a broader range of alternate design strategies for asymmetric photocatalysis might be possible.

Enantioselective, intermolecular [2+2] photocycloaddition reactions of 3-acetoxyquinolone: Total synthesis of (-)-pinolinone

The natural product (-)-pinolinone was synthesised via a concise route (six steps, 17% overall yield) from 3-acetoxyquinolone, employing an enantioselective intermolecular [2+2] photocycloaddition as the key step. The Royal Society of Chemistry 2014.