Production Method 1

864550-40-3

Reaction Conditions

1.1 Reagents: 1,3-Dibromo-5,5-dimethylhydantoin ,  Sulfuric acid ;  8 h, rt
2.1 Reagents: Iron ,  Hydrochloric acid Solvents: Methanol ,  1,4-Dioxane ,  Water ;  4 h, 80 °C

Reference

4,6-Substituted-1H-indazoles as potent IDO1/TDO dual inhibitors

Yang, Lingling; et al, Bioorganic & Medicinal Chemistry, 2019, 27(6), 1087-1098

Production Method 2

95192-64-6

864550-40-3

Reaction Conditions

1.1 Reagents: Pyridine Solvents: Ethanol ;  1 h, reflux
1.2 Reagents: Ammonium sulfide Solvents: Water ;  1 h, reflux; 2 h, reflux; reflux → rt
1.3 Solvents: Water ;  cooled

Reference

A Concise Total Synthesis of Breitfussin A and B

Pandey, Sunil Kumar; et al, Organic Letters, 2015, 17(1), 122-125

5-Bromo-2-methyl-3-nitroaniline Raw materials

• 5-bromo-2-methyl-1,3-dinitro-benzene

5-Bromo-2-methyl-3-nitroaniline Preparation Products

• 5-Bromo-2-methyl-3-nitroaniline (864550-40-3)

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• 4. Alumina grafted SBA-15 sustainable bifunctional catalysts for direct cross-coupling of benzylic alcohols to diarylmethanes?
  Chandran Rajendran,Govindaswamy Satishkumar,Charlotte Lang,Eric M. Gaigneaux Catal. Sci. Technol., 2020,10, 2583-2592
• 5. An arsenic trioxide nanoparticle prodrug (ATONP) potentiates a therapeutic effect on an aggressive hepatocellular carcinoma model via enhancement of intratumoral arsenic accumulation and disturbance of the tumor microenvironment?
  Xin Fu,Qing-rong Liang,Rong-guang Luo,Yan-shu Li,Xiao-ping Xiao,Lu-lu Yu,Wen-zhe Shan,Guang-qin Fan J. Mater. Chem. B, 2019,7, 3088-3099

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Nitrobenzenes
• Solvents and Organic Chemicals Organic Compounds Amines/Sulfonamides

Introduction to 5-Bromo-2-methyl-3-nitroaniline (CAS No. 864550-40-3)

5-Bromo-2-methyl-3-nitroaniline (CAS No. 864550-40-3) is a versatile organic compound that has garnered significant attention in the fields of organic chemistry, pharmacology, and materials science. This compound, characterized by its bromine, methyl, and nitro substituents on the aromatic ring, exhibits unique chemical properties that make it a valuable building block in various synthetic processes. Recent advancements in synthetic methodologies have further enhanced its utility, particularly in the development of advanced materials and bioactive compounds.

The structure of 5-bromo-2-methyl-3-nitroaniline is defined by the presence of three key functional groups: the bromine atom at position 5, the methyl group at position 2, and the nitro group at position 3 of the aniline ring. These substituents not only influence the electronic properties of the molecule but also play a crucial role in determining its reactivity and stability. The nitro group, being a strong electron-withdrawing group, significantly impacts the compound's redox behavior, making it a promising candidate for applications in electrochemistry and energy storage systems.

Recent studies have explored the potential of brominated aromatic amines like 5-bromo-2-methyl-3-nitroaniline in the synthesis of advanced polymers and high-performance materials. For instance, researchers have demonstrated that this compound can serve as a precursor for constructing conjugated polymers with tailored electronic properties. These polymers exhibit exceptional charge transport characteristics, making them suitable for applications in organic electronics, such as light-emitting diodes (LEDs) and photovoltaic devices.

In addition to its role in materials science, 5-bromo-2-methyl-3-nitroaniline has shown promise in medicinal chemistry. The compound's ability to undergo various substitution reactions has enabled its use as an intermediate in the synthesis of bioactive molecules with potential therapeutic applications. Recent findings highlight its utility in designing inhibitors for key enzymes involved in neurodegenerative diseases, such as Alzheimer's disease.

The synthesis of 5-bromo-2-methyl-3-nitroaniline typically involves multi-step processes that combine nucleophilic aromatic substitution and nitration reactions. Researchers have optimized these processes to achieve high yields and purity levels, ensuring scalability for industrial applications. Furthermore, advancements in catalytic systems have facilitated more efficient pathways for synthesizing this compound, reducing production costs and environmental impact.

From an environmental perspective, understanding the degradation pathways of brominated aromatic compounds like 5-bromo-2-methyl-3-nitroaniline is crucial for assessing their ecological impact. Recent studies have investigated microbial degradation mechanisms under various environmental conditions, providing insights into their persistence and biodegradability.

In conclusion, 5-bromo-2-methyl-3-nitroaniline (CAS No. 864550-40-3) stands out as a multifaceted compound with diverse applications across multiple disciplines. Its unique chemical properties and reactivity continue to drive innovative research efforts, paving the way for new discoveries in materials science, pharmacology, and beyond.

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