3,4-Dichloro-2-nitroaniline
[CAS# 958804-40-5]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Amine
• Name: 3,4-Dichloro-2-nitroaniline
• Molecular Formula: C₆H₄Cl₂N₂O₂
• Molecular Weight: 207.01
• CAS Registry Number: 958804-40-5
• SMILES: C1=CC(=C(C(=C1N)[N+](=O)[O-])Cl)Cl

Discovory and Applicatios

3,4-Dichloro-2-nitroaniline is a chemical compound with the molecular formula C6H4Cl2N2O2, widely recognized for its role in the production of dyes, pigments, and agricultural chemicals. This compound is part of the aromatic amine class, which consists of compounds where an amino group is directly bonded to an aromatic ring, in this case, substituted with chlorine and nitro groups.

The discovery and synthesis of 3,4-Dichloro-2-nitroaniline can be traced back to the early developments in organic chemistry when researchers were exploring the reactivity of substituted anilines. The introduction of chlorine and nitro groups to the aniline structure was of particular interest because of the resulting compound’s ability to undergo further chemical transformations. The synthesis typically involves the nitration of 3,4-dichloroaniline, where the nitro group is introduced through the reaction of nitric acid with the chloroaniline compound under controlled conditions.

One of the primary applications of 3,4-Dichloro-2-nitroaniline is in the dye and pigment industry. Due to its stability and color properties, it is used as an intermediate in the synthesis of various azo dyes. Azo dyes are a class of dyes characterized by the presence of one or more azo bonds (N=N), which link two aromatic groups. The dichloro-nitro substitution pattern in 3,4-Dichloro-2-nitroaniline allows for the creation of dyes with specific shades and fastness properties, making them suitable for use in textiles, plastics, and inks.

In addition to its use in dyes, 3,4-Dichloro-2-nitroaniline is also important in the agricultural sector. It serves as a key intermediate in the synthesis of various agrochemicals, including herbicides and fungicides. These agrochemicals help protect crops from pests and diseases, contributing to higher agricultural productivity. The reactivity of 3,4-Dichloro-2-nitroaniline allows for the introduction of additional functional groups, leading to the development of compounds with targeted biological activity against specific pests or pathogens.

Furthermore, the compound is employed in research laboratories for studying the effects of substitution on the reactivity and properties of aniline derivatives. This research helps to expand the understanding of how different substituents influence the chemical behavior of aromatic amines, which is valuable for designing new compounds with desired properties.

However, while 3,4-Dichloro-2-nitroaniline is useful in various industrial applications, it is important to handle it with care due to its potential environmental and health risks. The compound is classified as hazardous, primarily because of its toxicity and potential environmental impact. Prolonged exposure can cause adverse health effects, and therefore, appropriate safety measures, including the use of protective equipment and proper disposal methods, should be followed to minimize exposure and environmental contamination.

In conclusion, 3,4-Dichloro-2-nitroaniline is a versatile compound with significant applications in the dye, pigment, and agricultural industries. Its discovery and utilization reflect the broader advancements in organic synthesis and the ongoing demand for specialized chemical intermediates. Despite its utility, the associated health and environmental risks necessitate careful handling and adherence to safety guidelines.