6924-99-8

Basic information

• Product Name: quinoxaline-2,3-dicarboxylic acid
• Synonyms: Quinoxaline-2,3-dicarboxylic acid
• CAS NO: 6924-99-8
• Molecular Formula: C₁₀H₆N₂O₄
• Molecular Weight: 218.1656
• EINECS: 230-046-9
• Mol File: 6924-99-8.mol

Chemical Properties

• Boiling Point: 430.6°C at 760 mmHg
• Flash Point: 214.2°C
• Density: 1.615g/cm³
• Vapor Pressure: 3.51E-08mmHg at 25°C
• Refractive Index: 1.734
• CAS DataBase Reference: quinoxaline-2,3-dicarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: quinoxaline-2,3-dicarboxylic acid(6924-99-8)
• EPA Substance Registry System: quinoxaline-2,3-dicarboxylic acid(6924-99-8)

Safety Data

• Hazardous Substances Data: 6924-99-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
Quinoxaline-2,3-dicarboxylic acid is utilized as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows for the development of new drugs with potential therapeutic benefits.
Used in Dye Production:
In the dye industry, quinoxaline-2,3-dicarboxylic acid serves as a building block for the creation of novel dyes with specific color properties and stability.
Used in Organic Compounds Synthesis:
quinoxaline-2,3-dicarboxylic acid is employed as a versatile starting material for the synthesis of other organic compounds, expanding the scope of organic chemistry.
Used in Antioxidant Applications:
Quinoxaline-2,3-dicarboxylic acid has been studied for its antioxidant properties, which could be beneficial in various applications, such as in the food industry or as a component of cosmetic products.
Used in Anticancer Research:
quinoxaline-2,3-dicarboxylic acid has shown potential anticancer properties, making it a candidate for further research and development in the field of oncology.
Used in Coordination Complex Development:
In coordination chemistry, quinoxaline-2,3-dicarboxylic acid is used to form coordination complexes, which have applications in areas such as catalysis and materials science.
Used in Organometallic Chemistry:
As a ligand, quinoxaline-2,3-dicarboxylic acid plays a crucial role in organometallic chemistry, contributing to the development of new organometallic compounds with potential applications in various industries.

Upstream product

• 87-69-4 L-Tartaric acid 
• 76039-54-8 2-Methyl-pyrrolo[3,4-b]quinoxaline-1,3-dione 
• 95-54-5 1,2-diamino-benzene 
• 54107-99-2 dimethyl quinoxaline-2,3-dicarboxylate 
• 146651-75-4 tert–butyl (2–aminophenyl)carbamate 
• 866-17-1 disodium 2,2,3,3-tetrahydroxybutane-1,4-dioate 
• 96331-69-0 cyclohepta[b]quinoxalin-8-one oxime 
• 92-82-0 Phenazin 
• 545-26-6 gitoxigenin 

Downstream Products

• 54107-99-2 dimethyl quinoxaline-2,3-dicarboxylate 
• 91-19-0 2,3-diethynylquinoxaline 
• 879-65-2 quinoxaline-2-carboxylic acid 
• 5660-34-4 quinoxaline-2,3-dicarboxylic acid anhydride 
• 37648-53-6 2-(p-tolyl)-1H-pyrrolo[3,4-b]quinoxaline-1,3(2H)-dione 

Relevant articles and documents

Method for preparing nitrogen-containing six-membered ring dicarboxylic acid

The invention relates to compound preparation, particularly to a method for preparing nitrogen-containing six-membered ring dicarboxylic acid from a benzo nitrogen-containing six-membered ring compound. According to the method, a raw material compound and a sodium chlorate aqueous solution are catalyzed under an acidic condition to obtain nitrogen-containing six-membered ring dicarboxylic acid, wherein the raw material is a nitrogen-containing six-membered heterocyclic benzocyclic compound. According to the invention, the catalyst of the reaction system is low in toxicity and low in cost, no new impurity is generated in the post-treatment step, and large-scale production is facilitated.

Hypervalent iodine(iii)-induced oxidative [4+2] annulation of o-phenylenediamines and electron-deficient alkynes: Direct synthesis of quinoxalines from alkyne substrates under metal-free conditions

Hypervalent iodine(iii)-induced oxidative [4+2] annulation of o-phenylenediamines and electron-deficient alkynes under metal-free conditions has been developed. The reaction allows for direct access to quinoxalines bearing two electron-withdrawing groups in an efficient manner.

Synthesis, and pharmacological screening of novel sulfamoylphenylcarbamoylquinoxaline derivatives as anti-inflammatory, analgesic and antitumour agents

Treatment of quinoxaline-2,3-dicarboxylic acid anhydride with some sulfonamides gave 3-sulfamoylphenylcarbamoylquinoxaline-2-carboxylic acid derivatives. While fusing the anhydride with the same sulfonamides produced the corresponding 3-sulfamoylphenylcarbamoylquinoxalines. On refluxing 3-sulfamoylphenylcarbamoyl derivatives with acetic anhydride gave the pyrrolo[3,4-d]quinoxaline derivatives. The imide linkage in the latter compound was opened via its reaction with amines under fusion conditions and quinoxalin-2,3-diamides were obtained. The pharmacological evaluation for some of the synthesised compounds revealed that in anti-inflammatory activity in chronic models, 3-{[4-(N-pyrimidin-2-ylsulfamoyl)phenyl]carbamoyl}quinoxaline-2- carboxylic acid was equipotent to the reference drug, indomethacin as well as having nonulcerogenic effect. All tested compounds showed moderate analgesic activity compared to the reference drug. The antitumour activity for the tested compounds showed that 3-{[4-(N-(5-methylisoxazol-3-yl)sulfamoyl)phenyl] carbamoyl}quinoxaline-2-carboxylic acid, 4-(1,3-dioxo-1H-pyrrolo[3,4-b] quinoxalin-2(3H)-yl)-N-(pyrimidin-2-yl)-benzenesulfonamide and N-carbamimidoyl-4-(1,3-dioxo-1H-pyrrolo[3,4-b]quinoxalin-2(3H)-yl) benzenesulfonamide were the most effective against the liver carcinoma cell line showing IC50 values 0.5, 0.79 and 1.84 IC50 μg mL-1, respectively.

SYNTHESE VON CHINOXALIN- UND INDOL-2,3-DICARBONSAUREIMIDEN

Quinoxaline- and indole-2,3-dicarboxylic imides 7,8 are prepared by reaction of halogenactive maleimides 1,2 with sodium azide.Further derivatives of these heterocyclic series are available by secondary reactions of the imides.