7739-04-0

Basic information

• Product Name: 2,3-dimethyl-1,2,3,4-tetrahydroquinoxaline
• Synonyms: 1,2,3,4-Tetrahydro-2,3-dimethylquinoxaline; 2,3-Dimethyl-1,2,3,4-tetrahydroquinoxaline
• CAS NO: 7739-04-0
• Molecular Formula: C₁₀H₁₄N₂
• Molecular Weight: 162.2316
• Mol File: 7739-04-0.mol

Chemical Properties

• Boiling Point: 287.2°C at 760 mmHg
• Flash Point: 166.9°C
• Density: 0.963g/cm³
• Vapor Pressure: 0.00252mmHg at 25°C
• Refractive Index: 1.505
• CAS DataBase Reference: 2,3-dimethyl-1,2,3,4-tetrahydroquinoxaline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-dimethyl-1,2,3,4-tetrahydroquinoxaline(7739-04-0)
• EPA Substance Registry System: 2,3-dimethyl-1,2,3,4-tetrahydroquinoxaline(7739-04-0)

Safety Data

• Hazardous Substances Data: 7739-04-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
2,3-dimethyl-1,2,3,4-tetrahydroquinoxaline is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows for the creation of complex organic compounds that can be utilized in the development of new drugs.
Used in Agrochemical Production:
2,3-dimethyl-1,2,3,4-tetrahydroquinoxaline is also used in the production of agrochemicals, where its properties contribute to the formulation of effective products for agricultural applications.
Used in Medicinal Chemistry Research:
2,3-dimethyl-1,2,3,4-tetrahydroquinoxaline serves as a building block in medicinal chemistry, where it is used to prepare complex organic compounds for research purposes. Its versatility in synthesis makes it a valuable tool in the development of new bioactive compounds.
Used in Material Science:
With potential applications in the development of new materials, 2,3-dimethyl-1,2,3,4-tetrahydroquinoxaline is used as a starting material in material science research. Its properties may contribute to the creation of innovative materials with unique characteristics.

Upstream product

• 2379-55-7 2,3-dimethylquinoxaline 
• 78-93-3 butanone 
• 106-89-8 epichlorohydrin 
• 88-74-4 2-nitro-aniline 
• 431-03-8 dimethylglyoxal 
• 91-19-0 2,3-diethynylquinoxaline 
• 917-64-6 methyl magnesium iodide 
• 917-54-4 methyllithium 
• 95-54-5 1,2-diamino-benzene 
• 64-17-5 ethanol 
• 4091-39-8 3-chloro-2-butanone 

Downstream Products

• 2379-55-7 2,3-dimethylquinoxaline 
• 857763-04-3 2-(4-chlorophenethyl)-3-methylquinoxaline 
• 1721-89-7 2,3-dimethylquinoline 
• 22465-86-7 1-benzoyl-2r,3c-dimethyl-1,2,3,4-tetrahydro-quinoxaline 
• 22465-87-8 1,4-dibenzoyl-2r,3c-dimethyl-1,2,3,4-tetrahydro-quinoxaline 

Relevant articles and documents

Tetrabutylammonium Bromide-Catalyzed Transfer Hydrogenation of Quinoxaline with HBpin as a Hydrogen Source

A metal-free environmentally benign, simple, and efficient transfer hydrogenation process of quinoxaline has been developed using the HBpin reagent as a hydrogen source. This reaction is compatible with a variety of quinoxalines offering the desired tetrahydroquinoxalines in moderate-to-excellent yields with Bu4NBr as a noncorrosive and low-cost catalyst.

A quantum-chemical approach to develop tetrahydroquinoxaline as potent ferroptosis inhibitors

Ferroptosis is a recently characterized form of regulated necrosis with the iron-dependent accumulation of (phospho)lipid hydroperoxides (LOOH). It has attracted considerable attention for its putative involvement in diverse pathophysiological processes, such as cardiovascular disease and neurodegeneration. Here we describe the discovery of tetrahydroquinoxaline, a novel scaffold of ferroptosis inhibitors based on quantum chemistry methods. Tetrahydroquinoxaline deviates showed very good inhibition of ferroptosis, while being non cytotoxic for human cancer cells. And, the advantage of them is their small molecular weight (MW. = 148 Da) that can be coupled with other drugs to form multi-target drugs to better meet the treatment of complicated diseases.

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.

Utilization of renewable formic acid from lignocellulosic biomass for the selective hydrogenation and/or N-methylation

Lignocellulosic biomass is one of the most abundant renewable sources in nature. Herein, we have developed the utilization of renewable formic acid from lignocellulosic biomass as a hydrogen source and a carbon source for the selective hydrogenation and further N-methylation of various quinolines and the derivatives, various indoles under mild conditions in high efficiencies. N-methylation of various anilines is also developed. Mechanistic studies indicate that the hydrogenation occurs via a transfer hydrogenation pathway.

Silver-Catalyzed Reduction of Quinolines in Water

A ligand- and base-free silver-catalyzed reduction of quinolines and electron-deficient aromatic N-heteroarenes in water has been described. Mechanistic studies revealed that the effective reducing species was Ag-H. This versatile catalytic protocol provided facile, environmentally friendly, and practical access to a variety of 1,2,3,4-tetrahydroquinoline derivatives at room temperature.

Tetrahydroquinoxaline compound, and preparation method and application thereof

The invention provides a tetrahydroquinoxaline compound, and a preparation method and application thereof. The chemical structure is shown in a formula I: the tetrahydroquinoxaline compound has good cell ferroptosis inhibition activity, and can be used fo

Switchable hydrogenation with a betaine-derived bifunctional Ir-NHC catalyst

A bifunctional iridium catalyst based on the 'uracil-abnormal NHC' hybrid ligand platform was developed for switchable hydrogenation of quinoxalines. Control studies suggested heterolytic H2 activation via a metal-ligand bifunctional operation to generate Ir-H and an adjacent protic O-H group for facile H+/H- transfer to quinoxaline. The presence of a base blocked the most essential H+-transfer step thus switching off the catalysis, while an acid stimulus reversed the action to switch on the reaction again.

Transfer hydrogenation of nitrogen heterocycles using a recyclable rhodium catalyst immobilized on bipyridine-periodic mesoporous organosilica

Transfer hydrogenation of unsaturated nitrogen heterocycles using a rhodium catalyst immobilized on bipyridine-periodic mesoporous organosilica (BPy-PMO) is described. The immobilized catalyst was prepared by mixing [Cp?RhCl2]2 (Cp?

Aerobic oxidative dehydrogenation of N-heterocycles catalyzed by cobalt porphyrin

An efficient catalytic procedure has been developed for the aerobic oxidative dehydrogenation of N-heterocycles by cobalt porphyrin in the absence of any additives. The catalytic system could tolerate various 1,2,3,4-tetrahydroquinoline derivatives and some other N-heterocycles. The corresponding N-heteroaromatics could be obtained in 59–86% yields. The mechanism investigation suggested that the aerobic oxidative dehydrogenation might proceed with imine intermediate through radical paths.

Asymmetric Transfer Hydrogenations of 2,3-Disubstituted Quinoxalines with Ammonia Borane

An asymmetric transfer hydrogenation of 2,3-disubstituted quinoxalines using a chiral frustrated Lewis pair of Piers' borane and (R)-tert-butylsulfinamide as the catalyst with ammonia borane as the hydrogen source has been successfully realized. For 2-alk