Quinoxaline-2,3-diol
[CAS# 15804-19-0]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Quinoline compound
• Name: Quinoxaline-2,3-diol
• Synonyms: 2,3-Dihydroxyquinoxaline
• Molecular Formula: C₈H₆N₂O₂
• Molecular Weight: 162.14
• CAS Registry Number: 15804-19-0
• EC Number: 239-901-0
• SMILES: C1=CC=C2C(=C1)NC(=O)C(=O)N2

Properties

• Density: 1.5±0.1 g/cm³, Calc.^*
• Melting Point: 300 ºC
• Index of Refraction: 1.762, Calc.^*
• Boiling Point: 470.9±40.0 ºC (760 mmHg), Calc.^*
• Flash Point: 238.6±27.3 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Hazard Statements: H302-H315-H318-H335
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P354+P338-P317-P319-P321-P330-P332+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Serious eye damage	Eye Dam.	1	H318
Eye irritation	Eye Irrit.	2A	H319
Eye irritation	Eye Irrit.	2	H319

Discovory and Applicatios

Quinoxaline-2,3-diol is a heterocyclic compound that has garnered significant attention in the fields of medicinal chemistry and material science due to its unique structural properties and biological activities. With the molecular formula C8H6N2O2, this compound features a bicyclic structure containing both nitrogen and hydroxyl functional groups, making it an attractive candidate for various applications.

The discovery of quinoxaline-2,3-diol can be traced back to ongoing research in the late 20th century, focusing on the synthesis and characterization of nitrogen-containing heterocycles. Researchers were particularly interested in the quinoxaline scaffold because of its prevalence in biologically active compounds, including antibiotics, anti-cancer agents, and other pharmaceuticals. The synthesis of quinoxaline derivatives typically involves the condensation of 1,2-diamines with α-dicarbonyl compounds, leading to a diverse array of quinoxaline structures.

Quinoxaline-2,3-diol has shown promising biological activities, including anti-inflammatory, antimicrobial, and anticancer properties. In vitro studies have demonstrated that this compound exhibits potent activity against various cancer cell lines, making it a candidate for further investigation in cancer therapy. The hydroxyl groups present in the molecule enhance its reactivity, allowing for modifications that can optimize its pharmacological properties. The ability to derivatize quinoxaline-2,3-diol opens up avenues for the design of novel therapeutics with improved efficacy and selectivity.

In addition to its medicinal applications, quinoxaline-2,3-diol is also utilized in material science. The compound has been investigated for its potential as a precursor in the synthesis of conducting polymers and organic semiconductors. Its unique electronic properties, coupled with the ability to form stable films, make it suitable for applications in organic electronics, such as organic light-emitting diodes (OLEDs) and organic photovoltaic devices. The incorporation of quinoxaline-2,3-diol into polymer matrices can enhance the performance of these materials, leading to improved device efficiencies.

Furthermore, quinoxaline-2,3-diol has been explored in the field of chemical sensors. Its ability to undergo redox reactions makes it a valuable candidate for the development of electrochemical sensors capable of detecting various analytes. Researchers have focused on integrating quinoxaline derivatives into sensor platforms to enhance sensitivity and selectivity, with applications ranging from environmental monitoring to biomedical diagnostics.

In summary, quinoxaline-2,3-diol is a versatile compound with significant potential in medicinal chemistry and material science. Its unique structure allows for diverse biological activities, making it a valuable candidate for drug development. Additionally, its applications in organic electronics and chemical sensing further underscore its importance in modern research. As studies continue, quinoxaline-2,3-diol may lead to the development of innovative therapies and advanced materials that can meet the challenges of contemporary science.