19853-64-6

Usage

Uses

Used in Pharmaceutical Industry:
6,7-Dichloroquinoxaline 98 is used as an active pharmaceutical ingredient for its antimicrobial and antiparasitic properties, contributing to the development of new drugs that combat various infections and parasitic diseases.
Used in Agrochemical Industry:
In agrochemicals, 6,7-Dichloroquinoxaline 98 is used as a key component in the formulation of pesticides and other crop protection products, leveraging its antimicrobial properties to protect crops from diseases and pests.
Used in Organic Chemistry Research:
6,7-Dichloroquinoxaline 98 is used as a building block and intermediate in the synthesis of heterocyclic compounds, which are essential in the development of various organic compounds with diverse applications in medicine, materials science, and other fields.

InChI:InChI=1/C8H4Cl2N2/c9-5-3-7-8(4-6(5)10)12-2-1-11-7/h1-4H

Upstream product

• 5348-42-5 4,5-Dichloro-1,2-phenylenediamine 
• 517-21-5 glyoxal sodium bisulfite 
• 766-09-6 1-ethyl-piperidine 
• 121-44-8 triethylamine 
• 131543-46-9 Glyoxal 
• 68836-13-5 6,7-dinitroquinoxaline 

Downstream Products

• 3476-89-9 1,2,3,4-tetrahydroquinoxaline 
• 73855-45-5 6-chloro-1,2,3,4-tetrahydroquinoxaline 
• 25983-13-5 6,7-dichloro-1,4-dihydroquinoxaline-2,3-dione 

Relevant academic research and scientific papers

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.

Synthesis of novel halogenated heterocycles based on o‐phenylenediamine and their interactions with the catalytic subunit of protein kinase ck2

Protein kinase CK2 is a highly pleiotropic protein kinase capable of phosphorylating hundreds of protein substrates. It is involved in numerous cellular functions, including cell viability, apoptosis, cell proliferation and survival, angiogenesis, or ER‐stress response. As CK2 activity is found perturbed in many pathological states, including cancers, it becomes an attractive target for the pharma. A large number of low‐mass ATP‐competitive inhibitors have already been developed, the majority of them halogenated. We tested the binding of six series of halogenated heterocyclic ligands derived from the commercially available 4,5‐dihalo‐benzene‐1,2‐diamines. These ligand series were selected to enable the separation of the scaffold effect from the hydrophobic interactions attributed directly to the presence of halogen atoms. In silico molecular docking was initially applied to test the capability of each ligand for binding at the ATP‐binding site of CK2. HPLC‐derived ligand hydrophobicity data are compared with the binding affinity assessed by low‐volume differential scanning fluorimetry (nanoDSF). We identified three promising ligand scaffolds, two of which have not yet been described as CK2 inhibitors but may lead to potent CK2 kinase inhibitors. The inhibitory activity against CK2α and toxicity against four reference cell lines have been determined for eight compounds identified as the most promising in nanoDSF assay.

Method for synthesizing quinoxaline compound under visible light induced iron catalysis condition

The invention belongs to the technical field of compound synthesis, and particularly relates to a method for synthesizing quinoxaline compounds under visible light induced iron catalysis conditions. The method comprises the following steps: by taking non-activated aliphatic amine and o-phenylenediamine as raw materials, under the action of a photosensitizer, under the illumination of visible light, reacting in a solvent at room temperature and under oxygen conditions to generate the quinoxaline compound. The method has better substrate universality and relatively mild reaction conditions, not only realizes synthesis of the quinoxaline compound for the first time, but also widens the field of organic synthesis.

Iron-catalyzed Minisci acylation of N-heteroarenes with α-keto acids

An efficient and mild protocol has been developed for the Minisci acylation reactions of nitrogen-containing heteroarenes with α-keto acids. Distinct from the conventional Minisci acylation conditions, the chemistry was performed using non-noble metal Fe(II), instead of expensive Ag(I) salt, as catalyst. A wide range of substrates, including aliphatic or aromatic α-keto acids, as well as various N-heteroarenes, proved to be compatible with the protocol. Scale-up experiment also demonstrates the practicality of the approach.

Elemental fluorine. Part 10.1 Selective fluorination of pyridine, quinoline and quinoxaline derivatives with fluorine-iodine mixtures

Selective fluorination of a range of pyridine and quinoline substrates to give corresponding 2-fluoro-derivatives can be readily achieved in high yield at room temperature using elemental fluorine-iodine mixtures. Reaction of fluorine with iodine forms, in situ, systems that function like sources of both iodonium and fluoride ions and fluorination of heterocyclic derivatives is suggested to proceed by fluoride ion attack on intermediate W-iodo-heterocyclic species. Quinoxaline derivatives react under similar conditions to give either the 2-fluoro- or 2,3-difluoro-quinoxaline derivatives depending on the ratio of fluorine passed through the solution. In related processes, pyridine can be alkoxylated upon reaction of an appropriate alcohol and fluorine.

THE FOUR 6-HALO-7-NITROQUINOXALINES

The study of relative nucleofugicities of nitro and halogen in quinoxalines required the synthesis of the four 6-halo-7-nitroquinoxalines 2a-d.The fluoro-, chloro- and bromo-derivatives were made from the commercially available or readily accessible 1,2-diamino-4-halobenzenes, using the nitration of the corresponding p-toluenesulfonamides.This scheme failed in the case of the iodo compound because of extensive nitro-deiodination.The synthesis of 6-iodo-7-nitroquinoxaline was finally achieved from m-fluoroiodobenzene by taking advantage of the high reactivity of fluorine, compared to iodine, in 2,4-dinitrohalobenzenes.