6309-61-1

Basic information

• Product Name: 1,4-DIHYDRO-6-METHYLQUINOXALINE-2,3-DIONE
• Synonyms: 1,4-DIHYDRO-6-METHYLQUINOXALINE-2,3-DIONE;2,3-DIHYDROXY-6-METHYLQUINOXALINE;6-METHYLQUINOXALINE-2,3-DIOL;6-METHYL-1,4-DIHYDROQUINOXALINE-2,3-DIONE;2,3-Dihydoxy-6-methylquinoxaline;1,4-DIHYDRO-6-METHYLQUINOLAXINE-2,3-DIONE;1,4-Dihydro-6-Methyl-2,3-quinoxalinedione;6-Methylquinoxaline-2,3-diol C9H8N2O2 [6309-61-1]
• CAS NO: 6309-61-1
• Molecular Formula: C₉H₈N₂O₂
• Molecular Weight: 176.17
• EINECS: 228-628-2
• Mol File: 6309-61-1.mol
• Article Data: 20

Chemical Properties

• Melting Point: 112 °C
• Boiling Point: 467 °C at 760 mmHg
• Flash Point: 236.2 °C
• Appearance: /
• Density: 1.28 g/cm³
• Vapor Pressure: 2.42E-09mmHg at 25°C
• Refractive Index: 1.576
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: slightly sol. in Dimethylformamide
• PKA: 10.61±0.20(Predicted)
• CAS DataBase Reference: 1,4-DIHYDRO-6-METHYLQUINOXALINE-2,3-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-DIHYDRO-6-METHYLQUINOXALINE-2,3-DIONE(6309-61-1)
• EPA Substance Registry System: 1,4-DIHYDRO-6-METHYLQUINOXALINE-2,3-DIONE(6309-61-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22
• Safety Statements: 24/25
• Hazardous Substances Data: 6309-61-1(Hazardous Substances Data)

Usage

General Description

1,4-Dihydro-6-methylquinoxaline-2,3-dione is a chemical compound with complex organic structures. This chemical compound belongs to the class of molecules known as quinoxalinones which are polycyclic aromatic compounds containing a benzene fused to a quinoxaline. Quinoxalines contain a ring system consisting of a benzene ring fused to a pyrazine ring. Its systematic name is 1,4-dihydro-6-methylquinoxaline-2,3(1H,4H)-dione. Further details on its physical properties, potential use, toxicity, and safety measures require more in-depth research and understanding of the compound.

InChI:InChI=1/C9H8N2O2/c1-5-2-3-6-7(4-5)11-9(13)8(12)10-6/h2-4H,1H3,(H,10,12)(H,11,13)

Upstream product

• 120-89-8 parabanic acid 
• 636-24-8 4-Methyl-benzene-1,2-diamine; hydrochloride 
• 496-72-0 4-methyl-1,2-diaminobenzene 
• 95-92-1 oxalic acid diethyl ester 
• 6153-56-6 oxalic acid dihydrate 
• 144-62-7 oxalic acid 
• 89-62-3 4-methyl-2-nitroaniline 
• 2439-01-2 morestan 
• 39267-05-5 2,3-dichloro-6-methylquinoxaline 
• 33368-89-7 6-methylquinoxaline 1,4-dioxide 

Downstream Products

• 39267-05-5 2,3-dichloro-6-methylquinoxaline 
• 1407513-30-7 2-chloro-6-methyl-3-(p-tolylethynyl)quinoxaline 
• 1407513-29-4 2-chloro-6-methyl-3-(phenylethynyl)quinoxaline 
• 1407513-35-2 6-methyl-2-p-tolyl-1H-pyrrolo[2,3-b]quinoxaline 
• 1407513-34-1 6-methyl-2-phenyl-1H-pyrrolo[2,3-b]quinoxaline 
• 1407513-37-4 6-methyl-1-(methylsulfonyl)-2-phenyl-1H-pyrrolo[2,3-b]quinoxaline 

Relevant articles and documents

-

-

Anti-MRSA drug discovery by ligand-based virtual screening and biological evaluation

S. aureus resistant to methicillin (MRSA) is one of the most-concerned multidrug resistant bacteria, due to its role in life-threatening infections. There is an urgent need to develop new antibiotics against MRSA. In this study, we firstly compiled a data set of 2,3-diaminoquinoxalines by chemical synthesis and antibacterial screening against S. aureus, and then performed cheminformatics modeling and virtual screening. The compound with the Specs ID of AG-205/33156020 was discovered as a new antibacterial agent, and was further identified as a Gyrase B (GyrB) inhibitor. In light of the common features, we hypothesized that the 6c as the representative of 2,3-diaminoquinoxalines also inhibited GyrB and eventually proved it. Via molecular docking and molecular dynamics simulations, we identified binding modes of AG-205/33156020 and 6c to the ATPase domain of GyrB. Importantly, these GyrB inhibitors inhibited the MRSA strains and showed selectivity to HepG2 and HUVEC. Taken together, this research work provides an effective ligand-based computational workflow for scaffold hopping in anti-MRSA drug discovery, and discovers two new GyrB inhibitors that are worthy of further development.

Choline Chloride-based Eutectic Mixtures for Greener Synthesis of Quinoxaline-2,3-diol Derivatives and Terephthalaldehyde bis-(2-Aminophenylimine)

-

A new solvent for the reaction of chlorination of hydroxyquinoxaline derivatives with vilsmeier reagent

A new efficient procedure for the chlorination of hydroxyquinoxaline derivatives into the corresponding chlorides is described. It has been found that the use of 1-chlorobutane produces the highest yield, reduces the time of reaction and facilitates direct formation of crystals without any purification.