59564-59-9

Basic information

• Product Name: 3,4-DIHYDRO-1H-QUINOXALIN-2-ONE
• Synonyms: 3,4-DIHYDRO-1H-QUINOXALIN-2-ONE;AKOS BC-1152;AURORA 6866;3,4-dihydroquinoxalin-2(1H)-one;2(1H)-Quinoxalinone, 3,4-dihydro-;3,4-Dihydro-2(1H)-quinoxalinone;3,4-Dihydroquinoxalin-2-one;3,4-Dihydroquinoxaline-2(1H)-one
• CAS NO: 59564-59-9
• Molecular Formula: C₈H₈N₂O
• Molecular Weight: 148.16
• Mol File: 59564-59-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: 140-143℃
• Boiling Point: 370.5 °C at 760 mmHg
• Flash Point: 183.4 °C
• Appearance: /
• Density: 1.186 g/cm³
• Vapor Pressure: 1.1E-05mmHg at 25°C
• Refractive Index: 1.564
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 13.24±0.20(Predicted)
• CAS DataBase Reference: 3,4-DIHYDRO-1H-QUINOXALIN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DIHYDRO-1H-QUINOXALIN-2-ONE(59564-59-9)
• EPA Substance Registry System: 3,4-DIHYDRO-1H-QUINOXALIN-2-ONE(59564-59-9)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 59564-59-9(Hazardous Substances Data)

Usage

General Description

3,4-Dihydro-1H-Quinoxalin-2-one is a chemical compound with the molecular formula C9H8N2O. It is a heterocyclic organic compound and a derivative of quinoxaline. 3,4-DIHYDRO-1H-QUINOXALIN-2-ONE has a bicyclic structure and is commonly used in the field of pharmaceuticals, agricultural chemicals, and materials science. It has demonstrated potential biological activities, including as an antifungal and anti-inflammatory agent. Additionally, it has been studied for its potential use in the development of new drugs for various medical applications. 3,4-DIHYDRO-1H-QUINOXALIN-2-ONE also has the ability to function as a ligand for metal ions in coordination chemistry.

InChI:InChI=1/C8H8N2O/c11-8-5-9-6-3-1-2-4-7(6)10-8/h1-4,9H,5H2,(H,10,11)

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 95-54-5 1,2-diamino-benzene 
• 79-11-8 chloroacetic acid 
• 65182-17-4 5,12-dihydro-5,12-diacetylquinoxalino<2,3-b>quinoxaline 

Downstream Products

• 15804-19-0 quinoxaline-2,3-dione 
• 53374-52-0 1-nitroso-3-keto-1,2,3,4-tetrahydroquinoxaline 
• 148858-09-7 ethyl 4,5-dihydroimidazo<1,5-a>quinoxaline-3-carboxylate 
• 1196-57-2 quinoxalin-2⁽¹⁾-one 
• 1040257-78-0 2-(2-hydroxybenzoyl)pyrrolo[1,2-a]quinoxalin-4(5H)-one 
• 67074-63-9 3,4-dihydro-4-methyl-2(1H)-quinoxalinone 
• 727375-01-1 4-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-3,4-dihydro-1H-quinoxalin-2-one 
• 103639-83-4 1-propyl-1,2,3,4-tetrahydroquinoxaline 
• 73855-46-6 1-ethyl-1,2,3,4-tetrahydroquinoxaline 
• 1196-57-2 2-hydroxyquinoxaline 
• 120589-79-9 benzyl 4-benzoyl-3,4-dihydro-2(1H)-quinoxalinone-1-acetate 
• 115699-61-1 ethyl 4-benzenesulfonyl-3,4-dihydro-2(1H)-quinoxalinone-1-acetate 
• 120589-78-8 ethyl 4-benzoyl-3,4-dihydro-2(1H)-quinoxalinone-1-acetate 
• 115699-68-8 4-benzenesulfonyl-3,4-dihydro-2(1H)-quinoxalinone-1-acetic acid 

Relevant articles and documents

O-H insertion and tandem N-H insertion/cyclization reactions using an iron porphyrin as catalyst with diazo compounds as carbene sources

Iron(III) tetraphenylporphyrin chloride, Fe(TPP)Cl, efficiently catalyzed the insertion of carbenes derived from methyl 2-phenyldiazoacetates into O-H bonds of aliphatic and aromatic alcohols, with yields generally above 80%. Although the analogous N-H insertions are rapid at room temperature, the O-H insertion reactions are slower and required heating in refluxing methylene chloride for about 8 hours using 1.0 mol.% catalyst. Fe(TPP)Cl was also found to be effective for tandem N-H insertion/cyclization reactions when 1,2-diamines and 1,2-alcoholamines were treated with diazo reagents to give piperazinones and morpholinones and related analogs such as quinoxalinones and benzoxazin-2-ones. This approach provides a new one-pot route for synthesizing these classes of heterocyclic compounds.

Electrochemical reduction of quinoxalinoquinoxaline

The electrochemical reduction of quinoxalinoquinoxaline gives fluoflavine (2) the structure of which is discussed.The electrochemical reduction of fluoflavine in acidic medium leads to a hexahydroquinolinoquinoxaline.A reduction mechanism is proposed based on cyclic voltammetry results and preparative electrolysis.The results obtained in the case of quinoxalinoquinoxaline are used to rationalize the results obtained in the case of pyrazinopyrazines and pyrazinoquinoxalines.