3,5-Dichloroanthranilic acid
[CAS# 2789-92-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic acid
• Name: 3,5-Dichloroanthranilic acid
• Synonyms: 2-Amino-3,5-dichlorobenzoic acid
• Molecular Formula: C₇H₅Cl₂NO₂
• Molecular Weight: 206.03
• CAS Registry Number: 2789-92-6
• EC Number: 220-520-3
• SMILES: C1=C(C=C(C(=C1C(=O)O)N)Cl)Cl

Properties

• Melting point: 227-230 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
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

3,5-Dichloroanthranilic acid was first synthesized through organic chemistry research endeavors aimed at exploring new chemical compounds with potential industrial and pharmaceutical applications. Chemists achieved its synthesis by chlorination of anthranilic acid, resulting in the introduction of chlorine atoms at the 3 and 5 positions of the benzene ring. This discovery marked a significant advancement in the field of organic synthesis, providing a novel compound with diverse properties and applications.

3,5-Dichloroanthranilic acid serves as a crucial intermediate in the synthesis of various pharmaceutical compounds. Its chlorinated benzene ring imparts desirable pharmacological properties, making it a valuable building block for drug development. Pharmaceutical researchers utilize this compound in the synthesis of analgesics, anti-inflammatories, and antimicrobial agents. Additionally, it finds application in the synthesis of dyes, pigments, and fluorescent compounds used in biological labeling and imaging techniques.

In the agricultural sector, 3,5-Dichloroanthranilic acid is utilized in the formulation of agrochemicals and herbicides. Its herbicidal properties make it effective in controlling weed growth and protecting crops from competition. Agrochemical companies incorporate this compound into herbicide formulations to enhance agricultural productivity and yield. Additionally, it finds application as a precursor in the synthesis of other agricultural chemicals, contributing to sustainable farming practices and crop protection.

3,5-Dichloroanthranilic acid serves as a versatile chemical intermediate in organic synthesis. Its functional groups enable the synthesis of a wide range of complex organic compounds, including pharmaceuticals, agrochemicals, and specialty chemicals. Organic chemists utilize this compound in various transformations, such as amide formation, esterification, and cyclization reactions. Its compatibility with different reaction conditions and its role as a key building block contribute to its widespread use in chemical synthesis.

In research laboratories, 3,5-Dichloroanthranilic acid is used as a tool compound for exploring new chemical reactions and developing innovative synthetic methodologies. Its unique structural features and reactivity patterns make it a valuable substrate for investigating reaction mechanisms and designing novel synthetic routes. Researchers leverage its properties to access diverse chemical space and develop efficient routes for the synthesis of complex molecules.

3,5-Dichloroanthranilic acid finds application in water treatment processes as a precursor for the synthesis of disinfection byproducts. Its chlorinated structure contributes to the formation of stable disinfection byproducts during chlorination processes, ensuring water safety and quality. Water treatment facilities utilize this compound to comply with regulatory standards and ensure the removal of pathogens and contaminants from drinking water supplies.