6639-79-8

Basic information

• Product Name: 6-CHLORO-2,3-DIOXO-1,2,3,4-TETRAHYDROQUINOXALINE
• Synonyms: 2,3-DIHYDROXY-6-CHLOROQUINOXALINE;6-CHLOROQUINOXALINE-2,3-DIOL;6-chloro-1,2,3,4-tetrahydroquinoxaline-2,3-dione;6-CHLORO-1,4-DIHYDRO-2,3-QUINOXALINEDIONE;6-CHLORO-2,3-DIOXO-1,2,3,4-TETRAHYDROQUINOXALINE;6-chloro-1,4-dihydro-3-quinoxalinedione;6-chloro-1,4-dihydroquinoxaline-2,3-dione;6-Chloro-2,3-dihydroxyqunoxaline
• CAS NO: 6639-79-8
• Molecular Formula: C₈H₅ClN₂O₂
• Molecular Weight: 196.59
• EINECS: 229-647-9
• Mol File: 6639-79-8.mol
• Article Data: 24

Chemical Properties

• Melting Point: 250℃
• Appearance: /
• Density: 1.475±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 9.59±0.20(Predicted)
• CAS DataBase Reference: 6-CHLORO-2,3-DIOXO-1,2,3,4-TETRAHYDROQUINOXALINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CHLORO-2,3-DIOXO-1,2,3,4-TETRAHYDROQUINOXALINE(6639-79-8)
• EPA Substance Registry System: 6-CHLORO-2,3-DIOXO-1,2,3,4-TETRAHYDROQUINOXALINE(6639-79-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 6639-79-8(Hazardous Substances Data)

Usage

Description

6-Chloro-2,3-dioxo-1,2,3,4-tetrahydroquinoxaline, also known as 6-chloroquinoxaline-2,3-diol, is a chemical compound with potential applications in various fields. It is characterized by its quinoxaline structure, which contains a chloro substituent at the 6th position and two hydroxyl groups at the 2nd and 3rd positions. 6-CHLORO-2,3-DIOXO-1,2,3,4-TETRAHYDROQUINOXALINE has been studied for its potential therapeutic effects and is considered a promising candidate for various applications.

Uses

Used in Pharmaceutical Industry:
6-Chloroquinoxaline-2,3-diol is used as a glycine receptor antagonist for its potential therapeutic effects in various conditions. It is being investigated for its use as an analgesic, anticonvulsant, neuroprotectant, and sedative-hypnotic.
As an Analgesic:
6-Chloroquinoxaline-2,3-diol is used to alleviate pain by blocking glycine receptors, which play a role in pain transmission in the central nervous system. By inhibiting these receptors, it can help reduce pain signals and provide relief to patients.
As an Anticonvulsant:
6-CHLORO-2,3-DIOXO-1,2,3,4-TETRAHYDROQUINOXALINE is also being studied for its potential use as an anticonvulsant, which can help prevent or reduce the severity of seizures in patients with epilepsy or other seizure disorders. Its glycine receptor antagonist properties may contribute to its anticonvulsant effects.
As a Neuroprotectant:
6-Chloroquinoxaline-2,3-diol has the potential to act as a neuroprotectant, which means it can help protect neurons from damage or degeneration. This property may be useful in the treatment of neurodegenerative diseases such as Alzheimer's, Parkinson's, or multiple sclerosis.
As a Sedative-Hypnotic:
In addition to its other potential uses, 6-chloroquinoxaline-2,3-diol is being investigated for its use as a sedative-hypnotic. This means it may help induce sleep or promote relaxation in patients with insomnia or other sleep disorders. Its effects on glycine receptors could contribute to its sedative and hypnotic properties.

InChI:InChI=1/C8H5ClN2O2/c9-4-1-2-5-6(3-4)11-8(13)7(12)10-5/h1-3H,(H,10,12)(H,11,13)

Upstream product

• 95-83-0 4-Chloro-1,2-phenylenediamine 
• 95-92-1 oxalic acid diethyl ester 
• 69065-87-8 (4-chloro-2-nitro-phenyl)-oxalamic acid ethyl ester 
• 5448-43-1 6-chloroquinoxaline 
• 34836-97-0 6-chloro-1,2-dihydro-2-oxoquinoxaline 4-oxide 
• 34797-69-8 p-chloro-o-nitroacetoacetanilide 
• 144-62-7 oxalic acid 
• 89-61-2 2,5-dichloronitrobenzene 
• 89-63-4 4-Chloro-2-nitroaniline 
• 64-18-6 formic acid 
• 7722-84-1 dihydrogen peroxide 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 15804-19-0 quinoxaline-2,3-dione 

Downstream Products

• 2958-87-4 2,3,6-trichloro-quinoxaline 
• 91895-34-0 2,6-dichloro-3-hydrazinoquinoxaline 
• 91895-38-4 4,8-dichloro-1-phenyl<1,2,4>triazolo<4,3-a>quinoxaline 
• 91895-37-3 4,8-dichloro-1-(trifluoromethyl)<1,2,4>triazolo<4,3-a>quinoxaline 
• 127710-59-2 (8-Chloro-1-ethyl-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl)-cyclohexyl-amine 
• 91896-47-8 8-chloro-4-ethylamino-1-phenyl-[1,2,4]triazolo[4,3-a]quinoxaline 
• 127710-60-5 (8-Chloro-1-ethyl-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl)-phenyl-amine 
• 91896-46-7 8-chloro-4-isopropylamino-1-phenyl-[1,2,4]triazolo[4,3-a]quinoxaline 
• 91896-54-7 8-chloro-4-diethylamino-1-phenyl-[1,2,4]triazolo[4,3-a]quinoxaline 
• 127710-76-3 (8-Chloro-1-trifluoromethyl-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl)-cyclohexyl-amine 
• 127710-79-6 8-Chloro-1-phenyl-4-piperazin-1-yl-[1,2,4]triazolo[4,3-a]quinoxaline 
• 91896-57-0 CP 66713 
• 127710-80-9 8-Chloro-1-(4-chloro-phenyl)-[1,2,4]triazolo[4,3-a]quinoxalin-4-ylamine 
• 91896-21-8 CP 66278 

Relevant articles and documents

Choline Chloride-based Eutectic Mixtures for Greener Synthesis of Quinoxaline-2,3-diol Derivatives and Terephthalaldehyde bis-(2-Aminophenylimine)

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Synthesis method of 2,3-dihydroxy-6-chloroquinoxaline

The invention relates to a synthetic method of 2,3-dihydroxy-6-chloroquinoxaline, and belongs to the technical field of organic synthesis. The synthesis method comprises the following synthesis steps:(1) adding 4-chloro-o-phenylene diamine, diethyl oxalate and an alkali into a reaction flask, controlling a reaction system to be at a negative pressure, and heating a reaction solution to reflux tostart a reaction; (2) after the reaction is finished, adding active carbon for de-coloration, and performing hot filtration to obtain filtrate I; (3) cooling the filtrate I obtained in the step (2) to0-5 DEG C, crystallizing for 1-2 hours, and filtering to obtain a filter cake. The method has the advantages that (1) the side reactions are reduced by reducing the reaction temperature; (2) the reaction substrate is activated by using an alkali, so that the reaction is promoted; (3) a byproduct namely ethanol is extracted through rectification to promote forward proceeding of the reaction, so that the reaction time is shortened; and (4) the product quality is improved, and a 2,3-dihydroxy-6-chloroquinoxaline standard substance meeting the requirements is obtained.

Rationalization of benzazole-2-carboxylate versus benzazine-3-one/ benzazine-2,3-dione selectivity switch during cyclocondensation of 2-aminothiophenols/phenols/anilines with 1,2-biselectrophiles in aqueous medium

The cyclocondensation reaction of 2-aminothiophenols with 1,2-biselectrophiles such as ethyl glyoxalate and diethyl oxalate in aqueous medium leads to the formation of benzothiazole-2-carboxylates via the 5-endo-trig process contrary to Baldwin's rule. On the other hand, the reaction of 2-aminophenols/anilines produced the corresponding benzazine-3-ones or benzazine-2,3-diones via the 6-exo-trig process in compliance with Baldwin's rule. The mechanistic insights of these cyclocondensation reactions using the hard-soft acid-base principle, quantum chemical calculations (density functional theory), and orbital interaction studies rationalize the selectivity switch of benzothiazole-2-carboxylates versus benzazine-3-ones/ benzazine-2,3-diones. The presence of water facilitates these cyclocondensation reactions by lowering of the energy barrier.