Production Method 1

114166-32-4

138330-47-9

106837-44-9

59146-96-2

80879-86-3

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Water ;  1.5 h, 120 °C
1.2 Reagents: Ammonia Solvents: Water ;  basified, 0 °C

Reference

One-pot reaction as an efficient method for rigid molecular tweezers

Havlik, Martin; et al, Organic Letters, 2008, 10(21), 4767-4769

Production Method 2

134-98-5

106837-44-9

59146-96-2

80879-86-3

Reaction Conditions

1.1 Reagents: Sulfuric acid ,  Nitric acid Solvents: Water ;  1 h, 0 °C
2.1 Reagents: Hydrochloric acid Solvents: Water ;  1.5 h, 120 °C
2.2 Reagents: Ammonia Solvents: Water ;  basified, 0 °C

Reference

One-pot reaction as an efficient method for rigid molecular tweezers

Havlik, Martin; et al, Organic Letters, 2008, 10(21), 4767-4769

Production Method 3

87-59-2

106837-44-9

59146-96-2

80879-86-3

Reaction Conditions

1.1 Solvents: Chloroform ;  2 h, rt
2.1 Reagents: Sulfuric acid ,  Nitric acid Solvents: Water ;  1 h, 0 °C
3.1 Reagents: Hydrochloric acid Solvents: Water ;  1.5 h, 120 °C
3.2 Reagents: Ammonia Solvents: Water ;  basified, 0 °C

Reference

One-pot reaction as an efficient method for rigid molecular tweezers

Havlik, Martin; et al, Organic Letters, 2008, 10(21), 4767-4769

2,3-dimethyl-5-nitroaniline Raw materials

• N-(2,3-Dimethylphenyl)acetamide
• N-(2,3-Dimethyl-4-nitrophenyl)acetamide
• N-(2,3-Dimethyl-6-nitrophenyl)acetamide
• 2,3-Dimethylaniline

2,3-dimethyl-5-nitroaniline Preparation Products

• 2,3-Dimethyl-6-nitroaniline (59146-96-2)
• 2,3-DIMETHYL-4-NITROANILINE (80879-86-3)
• 2,3-dimethyl-5-nitroaniline (106837-44-9)

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Professional Introduction to 2,3-dimethyl-5-nitroaniline (CAS No. 106837-44-9)

2,3-dimethyl-5-nitroaniline, identified by the Chemical Abstracts Service Number (CAS No.) 106837-44-9, is a significant organic compound that has garnered considerable attention in the field of pharmaceutical chemistry and material science. This aromatic amine derivative, characterized by its nitro and methyl substituents, exhibits a unique set of chemical properties that make it a valuable intermediate in the synthesis of various biologically active molecules. The compound’s structure, featuring a benzene ring with nitro and methyl groups at the 2nd and 3rd positions respectively, and a nitro group at the 5th position, contributes to its reactivity and utility in multiple chemical transformations.

The chemical structure of 2,3-dimethyl-5-nitroaniline imparts distinct electronic and steric properties, making it a versatile building block in organic synthesis. The presence of electron-withdrawing nitro groups enhances the electrophilicity of the aromatic ring, facilitating nucleophilic aromatic substitution reactions. Additionally, the methyl groups introduce steric hindrance, influencing reaction pathways and regioselectivity. These characteristics have been exploited in the development of novel synthetic methodologies and in the construction of complex molecular architectures.

In recent years, 2,3-dimethyl-5-nitroaniline has been extensively studied for its potential applications in pharmaceutical research. Its derivatives have been explored as intermediates in the synthesis of antimicrobial agents, anticancer drugs, and other therapeutic compounds. The nitro group can be further functionalized through reduction to an amine or through diazotization followed by coupling reactions, providing access to a wide range of pharmacologically relevant molecules. Furthermore, the compound’s ability to participate in metal-catalyzed cross-coupling reactions makes it a valuable precursor in the synthesis of heterocyclic compounds, which are prevalent in many modern drugs.

One of the most compelling aspects of 2,3-dimethyl-5-nitroaniline is its role in the development of advanced materials. Researchers have leveraged its aromatic system to design novel organic semiconductors and conductive polymers. The nitro groups serve as electron-withdrawing moieties, enhancing charge transport properties, while the methyl groups can be tailored to modify solubility and film-forming characteristics. These attributes have led to promising applications in flexible electronics, organic photovoltaics (OPVs), and sensors. The compound’s ability to form stable radicals also makes it a candidate for use in radical-mediated polymerization processes.

The synthesis of 2,3-dimethyl-5-nitroaniline typically involves nitration of pre-existing dimethylbenzenes (xylenes) followed by selective functionalization. Modern synthetic approaches often employ catalytic methods to improve yield and selectivity while minimizing byproduct formation. Advances in green chemistry have also led to the development of more sustainable synthetic routes, such as solvent-free reactions or those utilizing microwave irradiation to accelerate reaction times. These innovations align with global efforts to reduce environmental impact without compromising efficiency.

Recent studies have highlighted the pharmacological potential of derivatives derived from 2,3-dimethyl-5-nitroaniline. For instance, modifications at the nitro or amine positions have yielded compounds with significant antimicrobial activity against resistant bacterial strains. Additionally, structural analogs have shown promise as kinase inhibitors due to their ability to interact with specific binding pockets on target enzymes. The versatility of this scaffold allows for fine-tuning of biological activity through rational drug design principles.

The analytical characterization of 2,3-dimethyl-5-nitroaniline is another critical aspect that has seen considerable advancements. High-resolution mass spectrometry (HRMS), nuclear magnetic resonance (NMR) spectroscopy (both 1H and 13C), and infrared (IR) spectroscopy are routinely employed to confirm structural integrity and purity. High-performance liquid chromatography (HPLC) coupled with UV-Vis detection provides reliable quantitative analysis for both research and industrial applications. These analytical techniques ensure that researchers can confidently utilize 2,3-dimethyl-5-nitroaniline in downstream processes without concern for impurities or structural deviations.

The industrial significance of 2,3-dimethyl-5-nitroaniline cannot be overstated. Its role as an intermediate in fine chemical synthesis supports a broad spectrum of industries beyond pharmaceuticals. For example, it serves as a precursor in dye manufacturing where nitroaromatics contribute to vibrant colorants used in textiles and coatings. Furthermore, its derivatives find applications in agrochemicals as part of formulations designed to enhance crop protection strategies.

In conclusion,2,3-dimethyl-5-nitroaniline (CAS No. 106837-44-9) represents a cornerstone compound in modern chemical research with far-reaching implications across multiple disciplines. Its unique structural features enable diverse applications ranging from drug discovery to advanced materials science. As research continues to uncover new methodologies for its synthesis and functionalization,the utility and importance of this compound are poised to grow even further, solidifying its place as an indispensable tool for chemists worldwide.

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