39267-05-5

Basic information

• Product Name: 2,3-DICHLORO-6-METHYLQUINOXALINE
• Synonyms: 2,3-DICHLORO-6-METHYLQUINOXALINE;Quinoxaline, 2,3-dichloro-6-Methyl-
• CAS NO: 39267-05-5
• Molecular Formula: C₉H₆Cl₂N₂
• Molecular Weight: 213.06
• Mol File: 39267-05-5.mol

Chemical Properties

• Melting Point: 115 °C
• Boiling Point: 289.1 °C at 760 mmHg
• Flash Point: 156.2 °C
• Appearance: /
• Density: 1.418 g/cm³
• Vapor Pressure: 0.0039mmHg at 25°C
• Refractive Index: 1.651
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -4.59±0.48(Predicted)
• CAS DataBase Reference: 2,3-DICHLORO-6-METHYLQUINOXALINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DICHLORO-6-METHYLQUINOXALINE(39267-05-5)
• EPA Substance Registry System: 2,3-DICHLORO-6-METHYLQUINOXALINE(39267-05-5)

Safety Data

• Hazard Codes: Xi,N,Xn
• Statements: 22-41-51
• Safety Statements: 53-26-39-61
• WGK Germany: 2
• Hazardous Substances Data: 39267-05-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2,3-DICHLORO-6-METHYLQUINOXALINE is used as a building block for synthesizing other complex organic compounds due to its versatile chemical properties.
Used in Pharmaceutical Industry:
2,3-DICHLORO-6-METHYLQUINOXALINE is used as a potential pharmacological agent for its antimicrobial and antiproliferative activities, making it a candidate for the development of new drugs.
Used in Agrochemical Industry:
2,3-DICHLORO-6-METHYLQUINOXALINE is investigated for its potential use as a herbicide and pesticide, offering possible applications in controlling unwanted plant and insect growth.

InChI:InChI=1/C9H6Cl2N2/c1-5-2-3-6-7(4-5)13-9(11)8(10)12-6/h2-4H,1H3

Upstream product

• 6309-61-1 6-methylquinoxaline-2,3-dione 
• 496-72-0 4-methyl-1,2-diaminobenzene 
• 10026-13-8 phosphorus pentachloride 
• 6309-61-1 2,3-dihydroxy-6-methylquinoxaline 

Downstream Products

• 59715-45-6 5,6-dichloropyrazine-2,3-dicarboxylic acid 
• 1446432-83-2 (Z)-2-(2,4-diethoxyphenyl)-3-(2-(2,4-diethoxyphenyl)-2-phenylvinyl)-6-methylquinoxaline 
• 1446432-82-1 (Z)-2-(2,4-dimethoxy-3-methylphenyl)-3-(2-(2,4-dimethoxy-3-methylphenyl)-2-phenylvinyl)-6-methylquinoxaline 
• 1446432-80-9 (Z)-4-(3-(2-(2,4-dihydroxy-3-methylphenyl)-2-phenylvinyl)-6-methylquinoxalin-2-yl)-2-methylbenzene-1,3-diol 
• 1446432-79-6 (Z)-4-(3-(2-(2,4-dihydroxyphenyl)-2-phenylvinyl)-6-methylquinoxalin-2-yl)benzene-1,3-diol 
• 1448176-16-6 6-methyl-2-phenylfuro[2,3-b]quinoxaline 
• 1446433-01-7 (Z)-2-(2,4-diethoxy-3-methylphenyl)-3-(2-(2,4-diethoxy-3-methylphenyl)-2-p-tolylvinyl)-6-methylquinoxaline 
• 1446432-99-0 (Z)-2-(2,4-diethoxyphenyl)-3-(2-(2,4-diethoxyphenyl)-2-p-tolylvinyl)-6-methylquinoxaline 
• 1446432-97-8 (Z)-2-(2,4-dimethoxy-3-methylphenyl)-3-(2-(2,4-dimethoxy-3-methylphenyl)-2-p-tolylvinyl)-6-methylquinoxaline 
• 1446432-95-6 (Z)-2-(2,4-dimethoxyphenyl)-3-(2-(2,4-dimethoxyphenyl)-2-p-tolylvinyl)-6-methylquinoxaline 
• 1446432-93-4 (Z)-4-(3-(2-(2,4-dihydroxy-3-methylphenyl)-2-p-tolylvinyl)-6-methylquinoxalin-2-yl)-2-methylbenzene-1,3-diol 
• 1446432-91-2 (Z)-4-(3-(2-(2,4-dihydroxyphenyl)-2-p-tolylvinyl)-6-methylquinoxalin-2-yl)benzene-1,3-diol 
• 1407513-30-7 2-chloro-6-methyl-3-(p-tolylethynyl)quinoxaline 
• 1407513-29-4 2-chloro-6-methyl-3-(phenylethynyl)quinoxaline 

Relevant articles and documents

Novel molecular targeting anti-tumor aza-steroid derivative based on lipid toxicity and preparation and application thereof

The invention provides a novel molecular targeting anti-tumor aza-steroid derivative based on lipid toxicity and a preparation method and application thereof, and belongs to the field of chemical medicines. The derivative is a compound as shown in a formula I, or a salt thereof, or a stereoisomer thereof. The compound is low in toxicity or basically non-toxic to normal cells, has an obvious inhibition effect to tumor cell lines, particularly has good lipid toxicity selectivity to tumor cells such as liver cancer, lung cancer and the like in vivo, and has an obvious inhibition effect; meanwhile, the compound can effectively activate SREBP1 and PPAR gamma, inhibit lipid transport MTTP, cause lipid aggregation in tumor cells and cause lipid toxicity of the tumor cells. The compound can be used for treating liver cancer, lung cancer and the like in a molecular targeting manner, is low in toxicity or even non-toxic, and has a good application prospect.

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.

Method for preparing 2,3-dichloro-quinoxaline derivative through one-pot procedure

The invention belongs to the field of drug synthesis, and specifically relates to a new method for preparing 2,3-dichloro-quinoxaline derivative through one-pot procedure. According to the method, cheap o-phenylenediamine and oxalic acid are adopted as raw materials, and the cheap and easily available and environmentally friendly silica gel or methanesulfonic acid is adopted as a catalyst while steps of intermediate separation and purification are omitted; the method has the advantages of easiness in operation, low cost, mild reaction conditions and environmental friendliness and promotes industrial mass production.

A One-pot Facile Synthesis of 2,3-Dihydroxyquinoxaline and 2,3-Dichloroquinoxaline Derivatives Using Silica Gel as an Efficient Catalyst

An efficient one-pot reaction has been developed for the synthesis of 2,3-dichloroquinoxaline derivatives 3a–n. The reaction was performed in two steps via a silica gel catalyzed tandem process from o-phenylenediamine and oxalic acid, followed by addition of phosphorus oxychloride (POCl3). A variety of 2,3-dichloroquinoxalines have been obtained in good to excellent overall yields. Eight known compounds 3a–3h were characterized by IR, 1H-NMR, and mass spectroscopies. Compounds 3i–3n without spectroscopic data were characterized by IR, 1H-NMR, 13C-NMR, and mass spectroscopies.

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.

Synthesis, structural, catecholase, tyrosinase and DFT studies of pyrazoloquinoxaline derivatives

Six functional multidentate ligands: 2,3-bis(3,5-dimethyl-1H-pyrazol-1-yl) quinoxaline, L1, 2,3-bis(3,5-dimethyl-1H-pyrazol-1-yl)-6-nitroquinoxaline, L2, 2,3-bis(3,5-dimethyl-1H-pyrazol-1-yl)-6-methylquinoxaline, L3, 2-(3,5-dimethyl-1H-pyrazol-1-yl)-3-hydrazinyl-6-nitroquinoxaline L4, 2-chloro-3-(3,5-dimethyl-1H-pyrazol-1-yl)-6-methylquinoxaline, L5, 2-chloro-3-(3,5-dimethyl-1H-pyrazol-1-yl) quinoxaline, L6, and a new copper (II) complex, were prepared and evaluated for their catecholase activities at aerobic conditions. We found that, the reaction rate depends on: The nature of the substituents in the quinoxaline ring, counter anion, metal, concentration of ligand and the used solvent. The complex obtained in-situ from reaction of one equivalent of ligand L1 and two equivalents of Cu(CH3COO)2 in methanol showed the highest oxidation rate activity (V?=?33.48?μmol?L?1. min?1). In addition, geometry optimizations of the complexes in order to get better insight into the geometry and the electronic structure and chemical reactivity were carried out by means of DFT calculations.

Pyrrolo[2,3-b]quinoxalines as inhibitors of firefly luciferase: Their Cu-mediated synthesis and evaluation as false positives in a reporter gene assay

2-Substituted pyrrolo[2,3-b]quinoxalines having free NH were prepared directly from 3-alkynyl-2-chloroquinoxalines in a single pot by using readily available and inexpensive methane sulfonamide (or p-toluene sulfonamide) as an ammonia surrogate. The reaction proceeded in the presence of Cu(OAc)2 affording the desired product in moderate yield. The crystal structure analysis of a representative compound and its supramolecular interactions are presented. Some of the compounds synthesized exhibited inhibitory activities against luciferase that was supported by the predictive binding mode of these compounds with luciferase enzyme through molecular docking studies. The key observations disclosed here can alert users of luciferase reporter gene assays for possible false positive results due to the direct inhibition of luciferase.

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The present invention relates to compounds and methods which may be useful as inhibitors of H1R and/or H4R for the treatment or prevention of inflammatory, autoimmune, allergic, and ocular diseases.

HETEROCYCLIC INHIBITORS OF HISTAMINE RECEPTORS FOR THE TREATMENT OF DISEASE

The present invention relates to compounds and methods which may be useful as inhibitors of H1R and/or H4R for the treatment or prevention of inflammatory, autoimmune, allergic, and ocular diseases.

Synthesis of novel diphenylamine-based fluorescent styryl colorants and study of their thermal, photophysical, and electrochemical properties

Three novel "Y"-shaped acceptor-π-donor-π-acceptor-type compounds were synthesized from 4,4′-(hexylimino)bis(benzaldehyde) as a donor and 2-methylthiazolo[4,5-b]quinoxaline derivatives as strong electron acceptors condensed by classical Knoevenagel condensation. Their absorption, emission, and thermal properties and electrochemical stability were investigated. It was found that the strong electron acceptor-donor chromophoric system of these compounds showed high Stokes shift, excellent thermal stability, and electrochemical reversibility. The solvatochromic behavior of these colorants was studied by using various solvents such as toluene, chloroform, ethyl acetate, tetrahydrofuran, methanol, and N,N-dimethylformamide in increasing order of polarity. The dyes were characterized by means of elemental analysis, 1H NMR, and mass spectrometry. Springer-Verlag 2010.