2768-63-0

Basic information

• Product Name: 2,3-dimethylquinoxaline-5,8-dione
• Synonyms: 2,3-Dimethyl-5,8-quinoxalinedione
• CAS NO: 2768-63-0
• Molecular Formula: C₁₀H₈N₂O₂
• Molecular Weight: 188.1827
• Mol File: 2768-63-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 415.7°C at 760 mmHg
• Flash Point: 206.9°C
• Density: 1.329g/cm³
• Vapor Pressure: 4.04E-07mmHg at 25°C
• Refractive Index: 1.604
• CAS DataBase Reference: 2,3-dimethylquinoxaline-5,8-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-dimethylquinoxaline-5,8-dione(2768-63-0)
• EPA Substance Registry System: 2,3-dimethylquinoxaline-5,8-dione(2768-63-0)

Safety Data

• Hazardous Substances Data: 2768-63-0(Hazardous Substances Data)

Usage

Description

2,3-dimethylquinoxaline-5,8-dione, also known as DMQ, is a heterocyclic chemical compound with the molecular formula C10H8N2O2. It features a quinoxaline ring system adorned with two methyl groups at the 2nd and 3rd positions, and carbonyl groups at the 5th and 8th positions. 2,3-dimethylquinoxaline-5,8-dione is characterized by its orange to red color and is recognized for its potential applications across various fields due to its unique chemical properties.

Uses

Used in Pharmaceutical and Agrochemical Industries:
2,3-dimethylquinoxaline-5,8-dione serves as a crucial intermediate in the synthesis of various pharmaceuticals and agrochemicals, leveraging its chemical structure to form the backbone of different medicinal and pesticidal agents.
Used as a Marker in EPR Spectroscopy:
In the field of analytical chemistry, 2,3-dimethylquinoxaline-5,8-dione is utilized as a marker in electron paramagnetic resonance (EPR) spectroscopy. Its distinct color and properties make it suitable for detecting a range of free radicals and metal ions, thus playing a significant role in studying reactive species in chemical and biological systems.
Investigated for Organic Electronic Devices:
2,3-dimethylquinoxaline-5,8-dione is being explored for its potential use in organic electronic devices, capitalizing on its electronic properties to enhance the performance of organic semiconductors and other related technologies.
Explored for Photocatalytic Applications:
2,3-dimethylquinoxaline-5,8-dione is under investigation for its possible applications in photocatalysis, where its interaction with light could drive chemical reactions, offering a pathway to develop new methods for environmental remediation and energy production.
Studied for Antioxidant and Anti-inflammatory Properties:
DMQ has been studied for its potential as an antioxidant, which could help in neutralizing harmful free radicals in biological systems. Additionally, its anti-inflammatory properties are of interest, suggesting possible uses in treating conditions affected by inflammation.

Upstream product

• 19506-22-0 2,3-dimethyl-5,8-dimethoxyquinoxaline 
• 40328-95-8 2,3-diamino-1,4-dimethoxybenzene 
• 6945-76-2 1,4-dimethoxy-2,3-dinitrobenzene 
• 150-78-7 1,4-dimethoxybezene 
• 56183-38-1 5-hydroxy-2,3-dimethylquinoxaline 

Downstream Products

• 14334-07-7 6-(4-chlorophenyl)amino-2,3-dimethyl-5,8-quinoxalinedione 
• 1073276-97-7 2,3-dimethyl-6-(4-ethoxyphenyl)amino-5,8-quinoxalinedione 
• 1073276-99-9 6-(3,4-dichlorophenyl)amino-2,3-dimethyl-5,8-quinoxalinedione 
• 14334-06-6 2,3-dimethyl-6-(4-fluorophenyl)amino-5,8-quinoxalinedione 
• 134755-27-4 2,3-dimethyl-6-<2-(4-hydroxyphenyl)ethylamino>quinoxaline-5,8-dione 
• 173912-77-1 2,3-dimethyl-6-<<2-(2-hydroxyphenyl)ethyl>amino>quinoxaline-5,8-dione 

Relevant articles and documents

Identification of ortho-naphthoquinones as anti-AML agents by highly efficient oxidation of phenols

A straightforward method for synthesizing ortho-naphthoquinones was identified using an easily available cobalt–Schiff base complex. Efficient oxidation of phenols to ortho-naphthoquinones was useful in obtaining compounds with potent biological activity

3D-QSAR studies of heterocyclic quinones with inhibitory activity on vascular smooth muscle cell proliferation using pharmacophore-based alignment

The abnormal proliferation and migration of vascular smooth muscle cells (SMCs) play an important role in the pathology of coronary artery atherosclerosis and restenosis following angioplasty. It was reported that some heterocyclic quinone derivatives such as 6-arylamino-quinoxaline-5,8-diones and 6-arylamino-1H-benzo[d]imidazole-4,7-diones have inhibitory activity on rat aortic smooth muscle cell (RAoSMC) proliferation. To understand the structural basis for antiproliferative activity to design more potent agents, we generated pharmacophore models of representative molecules with high activity using Genetic Algorithm with Linear Assignment of Hypermolecular Alignment of Database (GALAHAD) and aligned a series of compounds to the selected pharmacophore model, then performed three-dimensional quantitative structure-activity relationship (3D-QSAR) studies using Comparative Molecular Field Analysis (CoMFA) and Comparative Molecular Similarity Indices Analysis (CoMSIA). Good cross-validated correlations were obtained with CoMFA (resulting in q2 of 0.734 and r2 of 0.947) and CoMSIA (resulting in q2 of 0.736 and r2 of 0.913). The IC50 values of the heterocyclic quinone derivatives on RAoSMC exhibited a strong correlation with steric and hydrophobic fields of the 3D structure of the molecules, resulting in the reliable prediction of inhibitory activity of the series of compounds.

Synthesis of quinoxalinequinones using ceric ammonium nitrate

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