3-Chloro-4-(pyridin-3-yl)-1,2,5-thiadiazole
[CAS# 131986-28-2]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Lactone and oxygen-containing heterocyclic compound >> Thiazole, thiophene and pyridine
• Name: 3-Chloro-4-(pyridin-3-yl)-1,2,5-thiadiazole
• Molecular Formula: C₇H₄ClN₃S
• Molecular Weight: 197.64
• CAS Registry Number: 131986-28-2
• EC Number: 681-123-2
• SMILES: C1=CC(=CN=C1)C2=NSN=C2Cl

Properties

• Density: 1.5±0.1 g/cm³, Calc.^*
• Melting point: 56 ºC (Expl.)
• Index of Refraction: 1.631, Calc.^*
• Boiling Point: 297.2±25.0 ºC (760 mmHg), Calc.^*
• Flash Point: 133.5±23.2 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07 Danger
• Hazard Statements: H301-H315-H318-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P273-P280-P301+P316-P302+P352-P304+P340-P305+P351+P338-P305+P354+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Serious eye damage	Eye Dam.	1	H318

Discovory and Applicatios

3-Chloro-4-(pyridin-3-yl)-1,2,5-thiadiazole is a heterocyclic compound that belongs to the thiadiazole family, characterized by a five-membered ring containing sulfur and nitrogen atoms. The compound's chemical structure is enhanced by the presence of a pyridin-3-yl group and a chlorine atom, which contribute to its unique physicochemical properties. These features make it an essential candidate for applications in pharmaceutical research, materials science, and agriculture.

The discovery of 3-chloro-4-(pyridin-3-yl)-1,2,5-thiadiazole is rooted in the development of thiadiazole derivatives, which have attracted attention for their biological and chemical versatility. The addition of a pyridinyl substituent introduces aromaticity and polarity, which are crucial for interactions in biological systems and further functionalization. The chlorine atom adds electron-withdrawing properties, modifying the compound's reactivity and binding potential.

Pharmaceutical research has highlighted the utility of this compound as a scaffold for drug development. Thiadiazoles are recognized for their antimicrobial, anti-inflammatory, and anticancer activities. The pyridinyl group in 3-chloro-4-(pyridin-3-yl)-1,2,5-thiadiazole enhances its interaction with biological targets such as enzymes or receptors, making it a promising lead compound. Preliminary studies suggest its potential against bacterial infections and inflammatory disorders, demonstrating its ability to act as a potent inhibitor of key biological pathways.

In the agrochemical sector, this compound has potential applications as a pesticide or herbicide due to its robust activity against pests and pathogens. Its chemical stability, attributed to the chlorine atom, ensures prolonged efficacy in agricultural environments. The pyridinyl group improves water solubility and systemic transport in plant systems, enhancing its functionality in crop protection formulations. Such applications align with efforts to develop more efficient and sustainable agrochemicals.

Beyond its biological applications, 3-chloro-4-(pyridin-3-yl)-1,2,5-thiadiazole is also of interest in materials science. The conjugated system of the thiadiazole ring and the pyridinyl group contributes to its electronic properties, making it useful in the design of semiconductors, organic light-emitting diodes (OLEDs), and photovoltaic devices. The compound's ability to participate in charge transfer processes is critical for such advanced materials. Furthermore, the chlorine substituent can fine-tune its electronic characteristics, enhancing performance in specific optoelectronic applications.

The compound’s role as a synthetic intermediate is another area of significance. Its structural features facilitate chemical modifications, allowing the synthesis of derivatives with tailored properties. This versatility is highly beneficial in creating novel molecules for diverse industrial and research purposes.

Efforts are ongoing to optimize the synthesis of 3-chloro-4-(pyridin-3-yl)-1,2,5-thiadiazole with an emphasis on green chemistry. These advances aim to make its production more sustainable while reducing environmental impacts. Additionally, research into its safety profile and environmental persistence is necessary to ensure its responsible use in industrial and agricultural settings.

In summary, 3-chloro-4-(pyridin-3-yl)-1,2,5-thiadiazole is a valuable compound with a wide range of applications in pharmaceuticals, agriculture, and materials science. Its unique structural attributes enable its versatility and underline its importance in scientific research and practical applications.

References

2004. By Hydrogen. Science of Synthesis, 13.
DOI: 10.1055/sos-SD-013-00458

2004. By Nitrogen. Science of Synthesis, 13.
DOI: 10.1055/sos-SD-013-00458

2004. From Cyanoaminium Salts. Science of Synthesis, 13.
DOI: 10.1055/sos-SD-013-00458