2,6-Dichloroisonicotinic acid
[CAS# 5398-44-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Pyridine derivative
• Name: 2,6-Dichloroisonicotinic acid
• Molecular Formula: C₆H₃Cl₂NO₂
• Molecular Weight: 192.00
• CAS Registry Number: 5398-44-7
• EC Number: 611-076-5
• SMILES: C1=C(C=C(N=C1Cl)Cl)C(=O)O

Properties

• Melting point: 210-211 ºC
• Water solubility: insoluble

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+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
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

2,6-Dichloroisonicotinic acid, also known as dichloroisocyanuric acid (DICA), was first synthesized and characterized in the mid-20th century as part of research efforts to develop new chemical compounds with antimicrobial properties. Chemists sought to explore the potential of isonicotinic acid derivatives as antimicrobial agents due to their structural similarities to other biologically active compounds. Through systematic modifications to the isonicotinic acid scaffold, the synthesis of 2,6-Dichloroisonicotinic acid was achieved, resulting in a compound with potent antimicrobial activity against a wide range of microorganisms. Its discovery marked a significant advancement in the field of antimicrobial chemistry, offering a promising candidate for various applications in medicine, agriculture, and industrial settings.

One of the primary applications of 2,6-Dichloroisonicotinic acid is in water treatment systems for disinfection purposes. It is commonly used as a disinfectant agent in swimming pools, spas, and municipal water treatment facilities to control microbial contamination and prevent the spread of waterborne diseases. 2,6-Dichloroisonicotinic acid exhibits broad-spectrum antimicrobial activity against bacteria, viruses, and algae commonly found in water sources. Its effectiveness in eliminating pathogens makes it a valuable tool for ensuring water safety and quality.

In agriculture, 2,6-Dichloroisonicotinic acid is used as a fungicide and bactericide to protect crops from microbial infections. It helps prevent the onset and spread of plant diseases caused by fungi and bacteria, contributing to higher crop yields and improved agricultural productivity. The antimicrobial properties of 2,6-Dichloroisonicotinic acid also make it useful for post-harvest preservation of fruits and vegetables. By inhibiting the growth of spoilage microorganisms, it extends the shelf life of perishable produce, reducing food waste and losses during storage and transportation.

In the pharmaceutical industry, 2,6-Dichloroisonicotinic acid is investigated for its potential as an antibacterial agent in the development of new drugs to combat antibiotic-resistant infections. Its ability to disrupt microbial growth makes it a promising candidate for addressing emerging challenges in antimicrobial therapy. The compound may also find applications in topical treatments for skin infections and dermatological conditions caused by bacteria. Formulations containing 2,6-Dichloroisonicotinic acid offer targeted antimicrobial action while minimizing systemic side effects, making them suitable for various dermatological applications.

2,6-Dichloroisonicotinic acid is used as a biocide in various industrial processes to control microbial contamination and maintain product quality. It is incorporated into cooling water systems, industrial cleaning agents, and paper manufacturing processes to inhibit the growth of bacteria and fungi. Due to its antimicrobial properties, 2,6-Dichloroisonicotinic acid is employed as a preservative in cosmetics and personal care products to prevent microbial spoilage and ensure product safety and stability during storage and use.

References

2023. Increased soluble sugar accumulation in postharvest peaches in response to different defense priming elicitors. Horticulture, Environment, and Biotechnology, 64(1).
DOI: 10.1007/s13580-022-00464-0