2,3-Dichloroquinoxaline
[CAS# 2213-63-0]

Identification

• Classification: Organic raw materials >> Heterocyclic compound
• Name: 2,3-Dichloroquinoxaline
• Molecular Formula: C₈H₄Cl₂N₂
• Molecular Weight: 199.04
• CAS Registry Number: 2213-63-0
• EC Number: 218-667-3
• SMILES: C1=CC=C2C(=C1)N=C(C(=N2)Cl)Cl

Properties

• Density: 1.5±0.1 g/cm³, Calc.^*
• Melting point: 150-155 °C
• Index of Refraction: 1.671, Calc.^*
• Boiling Point: 269.7±35.0 °C (760 mmHg), Calc.^*
• Flash Point: 142.9±11.5 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS06;GHS07 Danger
• Risk Statements: H301-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P273-P280-P301+P316-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	3	H311
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

2,3-Dichloroquinoxaline is a chlorinated derivative of quinoxaline, a bicyclic aromatic compound composed of two nitrogen atoms in the fused ring system. Its molecular formula is C8H4Cl2N2, and it is characterized by the presence of two chlorine atoms at the 2 and 3 positions of the quinoxaline ring. The compound has gained attention in various fields, particularly in medicinal chemistry and material science, due to its unique structural and chemical properties.

The discovery of 2,3-dichloroquinoxaline is rooted in the broader study of quinoxaline derivatives, which began in the late 19th century. Quinoxaline itself was first synthesized by the German chemist Emil Fischer in 1888, and its derivatives have since been investigated for their potential biological activities. The introduction of chlorine substituents enhances the reactivity and biological profile of the quinoxaline ring, leading to the synthesis of compounds with improved pharmacological properties. Researchers have identified 2,3-dichloroquinoxaline as a compound of interest due to its significant activity against various biological targets.

One of the key applications of 2,3-dichloroquinoxaline lies in its role as an anticancer agent. Studies have demonstrated that this compound exhibits cytotoxic effects on various cancer cell lines, including those of breast, lung, and colon cancers. The mechanism of action is believed to involve the inhibition of specific signaling pathways crucial for cancer cell proliferation and survival. The presence of the chlorine substituents enhances the compound's ability to interact with biological molecules, making it a promising candidate for further development in cancer therapeutics.

In addition to its anticancer properties, 2,3-dichloroquinoxaline has been explored for its antimicrobial activity. Research indicates that it possesses inhibitory effects against a range of bacterial and fungal strains, suggesting its potential as a novel antimicrobial agent. The compound's effectiveness in combating infections could be valuable, especially in the context of increasing antibiotic resistance observed in many pathogens.

2,3-Dichloroquinoxaline has also found applications in material science. Its unique chemical structure allows for its incorporation into polymeric systems, leading to the development of materials with enhanced properties. The compound's ability to act as a precursor in the synthesis of functionalized polymers makes it a valuable building block in the field of advanced materials. Researchers are investigating its use in coatings, adhesives, and other polymer-based applications that require specific chemical functionalities.

Furthermore, the compound has been studied for its potential role as a ligand in coordination chemistry. The nitrogen atoms in the quinoxaline ring can coordinate with metal ions, forming metal complexes that exhibit unique properties. These metal complexes can find applications in catalysis, sensing, and other fields where the modulation of metal ion activity is required.

The environmental impact of 2,3-dichloroquinoxaline is an important consideration, especially given the increasing emphasis on sustainable chemistry. Research is ongoing to evaluate the biodegradability and toxicity of this compound, particularly concerning its potential use in agricultural applications. Understanding its environmental profile will be crucial for its safe application in various fields.

In summary, 2,3-dichloroquinoxaline is a versatile compound with significant applications in medicinal chemistry, material science, and coordination chemistry. Its unique structure imparts notable biological activity, particularly as an anticancer and antimicrobial agent. Ongoing research continues to explore the potential of this compound, ensuring its relevance in both scientific and industrial applications.

References

2020. Synthesis and Antimicrobial Activity of Quinoxaline Based 1,2,3-Triazoles. Russian Journal of General Chemistry, 90(12).
DOI: 10.1134/s1070363220120257

2016. Synthesis of Quinoxaline Macrocycles. Quinoxalines.
DOI: 10.1007/978-3-319-29773-6_5

1977. Reaction of 2,2′,3,3′-tetrachloro-6,6′-diquinoxalyl with nucleophilic reagents. Chemistry of Heterocyclic Compounds, 13(3).
DOI: 10.1007/bf00470324