6957-19-3

Basic information

• Product Name: 2,3,6,7-TETRAMETHYLQUINOXALINE
• Synonyms: 2,3,6,7-TETRAMETHYLQUINOXALINE;Nsc66172
• CAS NO: 6957-19-3
• Molecular Formula: C12H14N2
• Molecular Weight: 186.25
• Mol File: 6957-19-3.mol

Chemical Properties

• Boiling Point: 301.7 °C at 760 mmHg
• Flash Point: 124.1 °C
• Appearance: /
• Density: 1.063 g/cm³
• Vapor Pressure: 0.00185mmHg at 25°C
• Refractive Index: 1.595
• CAS DataBase Reference: 2,3,6,7-TETRAMETHYLQUINOXALINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,6,7-TETRAMETHYLQUINOXALINE(6957-19-3)
• EPA Substance Registry System: 2,3,6,7-TETRAMETHYLQUINOXALINE(6957-19-3)

Safety Data

• Hazardous Substances Data: 6957-19-3(Hazardous Substances Data)

Usage

Uses

Used in Analytical Chemistry:
2,3,6,7-Tetramethylquinoxaline is used as a reagent for the detection and quantification of hydrogen peroxide, which is crucial in various analytical and biochemical applications. Its ability to react with hydrogen peroxide makes it a valuable tool in laboratories for assessing oxidative processes and related research.
Used in Pharmaceutical Development:
Leveraging its antioxidant properties and free radical scavenging capabilities, 2,3,6,7-Tetramethylquinoxaline is explored for its potential use in the development of pharmaceuticals. Its capacity to neutralize harmful reactive species can contribute to the creation of treatments aimed at combating oxidative stress-related conditions.
Used in Cosmetics Industry:
In the cosmetics sector, 2,3,6,7-Tetramethylquinoxaline is considered for its potential inclusion in formulations to provide antioxidant benefits to skincare and other beauty products. Its role could be to protect the skin from oxidative damage and to maintain the stability of the product itself.
Used in Food Additives:
The antioxidant properties of 2,3,6,7-Tetramethylquinoxaline also make it a candidate for use in food additives, where it could help to extend the shelf life of products by preventing oxidation and maintaining freshness.
Used in Organic Electronics and Optoelectronics:
2,3,6,7-Tetramethylquinoxaline has been investigated for its potential applications in the realm of organic electronics and optoelectronics. Its unique electronic properties could be harnessed in the development of new materials for use in electronic devices and photonic applications, contributing to advances in technology and innovation.

InChI:InChI=1/C12H14N2/c1-7-5-11-12(6-8(7)2)14-10(4)9(3)13-11/h5-6H,1-4H3

Upstream product

• 6957-19-3 2,3,6,7-tetramethylquinoxaline 
• 3171-45-7 4,5-dimethyl-1,2-phenylenediamine 
• 513-85-9 2.3-butanediol 
• 3298-98-4 7,8-dimethyl-2,3-bis(bromomethyl)quinoxaline 
• 431-03-8 dimethylglyoxal 
• 6972-71-0 4,5-dimethyl-2-nitrobenzenamine 

Relevant articles and documents

Flavosemiquinone Model Systems. Part 2. Methyl-substituted Quinoxaline Radical Ions

2,3-Dimethyl-, 6,7-dimethyl-, and 2,3,6,7-tetramethyl-quinoxaline were reduced in aprotic (THF) and acidic media (DMF - HClO4) to yield the corresponding quinoxaline radical anions and 1,4-dihydroquinoxaline radical cations.Analysis of their e.s.r. spectra was accomplished by computer simulation; a consistent assignment of coupling constants in quinoxaline radical ions could be made on the basis of the methyl substitution pattern.The hyperfine splitting is in agreement with Hueckel MO correlations and may be used to explain the spin distribution in flavosemiquinones.

NaOH-Mediated Direct Synthesis of Quinoxalines from o-Nitroanilines and Alcohols via a Hydrogen-Transfer Strategy

A NaOH-mediated sustainable synthesis of functionalized quinoxalines is disclosed via redox condensation of o-nitroamines with diols and α-hydroxy ketones. Under optimized conditions, various o-nitroamines and alcohols are well tolerated to generate the desired products in 44-99% yields without transition metals and external redox additives.

Iron-catalyzed one-pot synthesis of quinoxalines: Transfer hydrogenative condensation of 2-nitroanilines with vicinal diols

Here, we report iron-catalyzed one-pot synthesis of quinoxalines via transfer hydrogenative condensation of 2-nitroanilines with vicinal diols. The tricarbonyl (η4-cyclopentadienone) iron complex, which is well known as the Kn?lker complex, catalyzed the oxidation of alcohols and the reduction of nitroarenes, and the corresponding carbonyl and 1,2-diaminobenzene intermediates were generated in situ. Trimethylamine N-oxide was used to activate the iron complex. Various unsymmetrical and symmetrical vicinal diols were applied for transfer hydrogenation, resulting in quinoxaline derivatives in 49-98% yields. A plausible mechanism was proposed based on a series of control experiments. The major advantages of this protocol are that no external redox reagents or additional base is needed and that water is liberated as the sole byproduct. This journal is

Hydrogen Auto-transfer Synthesis of Quinoxalines from o-Nitroanilines and Biomass-based Diols Catalyzed by MOF-derived N,P Co-doped Cobalt Catalysts

A Co-based heterogeneous catalyst supported on N,P co-doped porous carbon (Co@NCP) is prepared via a facile in-situ doping-carbonization method. The Co@NCP composite features a large surface area, high pore volume, high-density and strong basic sites. Furthermore, doping of P atoms can regulate the electronic density of Co. Therefore, Co@NCP exhibits good performance for the synthesis of quinoxalines from o-nitroanilines and biomass-derived diols under alkali-free conditions.

Nickel-Catalyzed Direct Synthesis of Quinoxalines from 2-Nitroanilines and Vicinal Diols: Identifying Nature of the Active Catalyst

The inexpensive and simple NiBr2/1,10-phenanthroline system-catalyzed synthesis of a series of quinoxalines from both 2-nitroanilines and 1,2-diamines is demonstrated. The reusability test for this system was performed up to the seventh cycle, which afforded good yields of the desired product without losing its reactivity significantly. Notably, during the catalytic reaction, the formation of the heterogeneous Ni-particle was observed, which was characterized by PXRD, XPS, and TEM techniques.

Application of a reusable Co-based nanocatalyst in alcohol dehydrogenative coupling strategy: Synthesis of quinoxaline and imine scaffolds

A nitrogen doped carbon supported cobalt catalyzed efficient synthesis of imines and quinoxaline motifs is reported. Co(OAc)2-Phen/Carbon-800 (Co-phen/C-800) showed the superior reactivity compared to other materials prepared at different temperature, in the synthesis of quinoxalines by the coupling between diamines and diols. Moreover, applying the transfer hydrogenation and acceptorless dehydrogenative coupling strategy, imines and quinoxaline derivatives were synthesized from the nitro compounds. The practical applicability of this protocol was demonstrated by the gram-scale synthesis and the reusability of the catalyst upto 8th cycle. Furthermore, several kinetic experiments were carried out to realize the probable mechanism.

Cobalt complex catalyzed atom-economical synthesis of quinoxaline, quinoline and 2-alkylaminoquinoline derivatives

A new phosphine-free Co(ii) complex-catalyzed synthesis of various quinoxalines via dehydrogenative coupling of vicinal diols with both o-phenylenediamines and 2-nitroanilines is reported. This complex was also effective for the synthesis of quinolines. The practical aspect of this catalytic system was revealed by the one-pot synthesis of 2-alkylaminoquinolines.

Efficient synthesis of quinoxalines from 2-nitroanilines and vicinal diols via a rutheniumcatalyzed hydrogen transfer strategy

Via a ruthenium-catalyzed hydrogen transfer strategy, we have demonstrated a one-pot method for efficient synthesis of quinoxalines from 2-nitroanilines and biomass-derived vicinal diols for the first time. In such a synthetic protocol, the diols and the nitro group serve as the hydrogen suppliers and acceptors, respectively. Hence, there is no need for the use of external reducing agents. Moreover, it has the advantages of operational simplicity, broad substrate scope and the use of renewable reactants, offering an important basis for accessing various quinoxaline derivatives.

Glycerin and CeCl3 7H2O: A new and efficient recyclable reaction medium for the synthesis of quinoxalines

An efficient and environmentally benign process for the synthesis of quinoxalines has been developed using glycerine-cerium chloride as a reaction medium. This method is applicable to a variety of diketones and 1,2-phenylenediamines to afford the corresponding quinoxaline derivatives in excellent yields. The reaction medium was recovered and reused for further reactions without any problem. Taylor & Francis Group, LLC.

Asymmetric hydrogenation of 2-and 2,3-substituted ouinoxalines with chiral cationic ruthenium diamine catalysts

The enantioselective hydrogenation of 2-alkyl- and 2-aryl-subsituted quinoxalines and 2,3-disubstituted quinoxalines was developed by using the cationic Ru(η6-cymene)(monosulfonylated diamine)(BArF) system in high yields with up to 99% ee. The counteranion was found to be critically important for the high enantioselectivity and/or diastereoselectivity.