Production Method 1

1805578-60-2

943830-82-8

Reaction Conditions

1.1 Reagents: Iron ,  Ammonium chloride Solvents: Methanol ;  4 h, 80 °C

Reference

Red-shifted tetra-ortho-halo-azobenzenes for photo-regulated transmembrane anion transport

Kerckhoffs, Aidan; Bo, Zonghua; Penty, Samuel E.; Duarte, Fernanda; Langton, Matthew J., Organic & Biomolecular Chemistry, 2021, 19(41), 9058-9067

Production Method 2

943830-80-6

943830-82-8

Reaction Conditions

1.1 Reagents: Sodium hydroxide ,  Bromine Solvents: Water ;  cooled
1.2 cooled; 2 h, rt → reflux; cooled

Reference

Preparation of 4-aminopicolic acid derivative herbicides

, World Intellectual Property Organization, , ,

3-Bromo-2,6-dichloroaniline Raw materials

• 1-Bromo-2,4-dichloro-3-nitrobenzene
• Benzamide, 3-bromo-2,6-dichloro-

3-Bromo-2,6-dichloroaniline Preparation Products

• 3-Bromo-2,6-dichloroaniline (943830-82-8)

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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Chlorobenzenes
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Halobenzenes Chlorobenzenes

3-Bromo-2,6-Dichloroaniline: A Comprehensive Overview

3-Bromo-2,6-dichloroaniline, a derivative of aniline with bromine and chlorine substituents at the 3 and 2,6 positions respectively, is a compound of significant interest in various fields of chemistry. This compound, identified by the CAS number 943830-82-8, has been extensively studied for its unique properties and potential applications. Recent advancements in synthetic methodologies and analytical techniques have further enhanced our understanding of its structure, reactivity, and utility.

The synthesis of 3-bromo-2,6-dichloroaniline typically involves multi-step processes that require precise control over reaction conditions. One common approach involves the chlorination of aniline derivatives followed by bromination at specific positions. The regioselectivity of these reactions is influenced by the directing effects of substituents already present on the aromatic ring. For instance, the presence of electron-withdrawing groups like chlorine can direct incoming electrophiles to specific positions, ensuring the formation of the desired product. Recent studies have explored the use of catalytic systems to improve yield and selectivity in these reactions.

3-Bromo-2,6-dichloroaniline exhibits interesting physical and chemical properties due to its halogen substituents. The presence of bromine and chlorine atoms significantly affects the compound's solubility, melting point, and reactivity. For instance, its solubility in polar solvents is higher compared to its unsubstituted counterpart due to the electron-withdrawing nature of halogens. This property makes it suitable for various applications in organic synthesis where solubility is a critical factor.

In terms of applications, 3-bromo-2,6-dichloroaniline has found utility in the synthesis of heterocyclic compounds, which are important in pharmaceuticals and agrochemicals. Its ability to undergo nucleophilic aromatic substitution reactions makes it a valuable intermediate in constructing complex molecular frameworks. Recent research has highlighted its role in the synthesis of bioactive molecules targeting specific enzymes and receptors.

The environmental impact and degradation pathways of 3-bromo-2,6-dichloroaniline have also been subjects of recent investigations. Studies suggest that this compound undergoes biodegradation under certain conditions, though its persistence in specific environments remains a concern. Regulatory frameworks are increasingly focusing on minimizing the environmental footprint of such compounds through sustainable synthesis and disposal practices.

From a computational chemistry perspective, 3-bromo-2,6-dichloroaniline has been modeled using advanced quantum mechanical methods to understand its electronic structure and reactivity patterns. These studies provide insights into the compound's behavior under different reaction conditions and guide experimental chemists in optimizing synthetic routes.

In conclusion, 3-bromo-2,6-dichloroaniline stands as a testament to the versatility of halogenated aromatic compounds in modern chemistry. Its continued exploration across diverse fields underscores its importance as both a fundamental building block and a subject of cutting-edge research.

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• 62406-67-1(Benzenamine, 4-bromo-2,3,6-trichloro-)
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• 64186-91-0(Benzenamine,4-bromo-2,3,5,6-tetrachloro-)