970-76-3

Usage

Uses

Used in Dye and Pigment Production:
2,4-dinitro-N-(4-nitrophenyl)aniline is used as a key intermediate in the synthesis of dyes and pigments for various applications, including textiles, plastics, and printing inks. Its bright yellow color and chemical stability make it a valuable component in these industries.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 2,4-dinitro-N-(4-nitrophenyl)aniline is used as a chemical intermediate for the development of certain drugs. Its specific chemical properties allow it to be a building block in the synthesis of pharmaceutical compounds.
Used in Research and Development:
2,4-dinitro-N-(4-nitrophenyl)aniline is also utilized in research and development settings for the study of chemical reactions and the development of new chemical processes or products.
Safety Considerations:
Given its toxicity and potential carcinogenic properties, 2,4-dinitro-N-(4-nitrophenyl)aniline requires careful handling to prevent skin, eye, and respiratory irritation. It is essential to follow proper disposal and containment procedures to minimize the risk of ingestion or inhalation, which can be harmful to human health.

InChI:InChI=1/C12H8N4O6/c17-14(18)9-3-1-8(2-4-9)13-11-6-5-10(15(19)20)7-12(11)16(21)22/h1-7,13H

Upstream product

• 56-23-5 tetrachloromethane 
• 13916-77-3 bis-(4-nitro-phenyl)-nitroso-amine 
• 961-68-2 N-phenyl-2,4-dinitroaniline 
• 1821-27-8 N,N-bis(p-nitrophenyl)amine 
• 584-48-5 2,4-dinitrobromobenzene 
• 100-01-6 4-nitro-aniline 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 122-39-4 diphenylamine 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 
• 103859-52-5 (2-nitro-phenyl)-(4-nitroso-phenyl)-amine 
• 148-97-0 N-hydroxy-N-nitroso-benzenamine 
• 99-65-0 meta-dinitrobenzene 
• 586-96-9 Nitrosobenzene 

Downstream Products

• 58133-67-8 N-methyl-N-(4-nitrophenyl)-2,4-dinitroaniline 
• 2908-76-1 bis(2,4-dinitrophenyl)amine 

Relevant academic research and scientific papers

Prodrugs for nitroreductase-based cancer therapy-3: Antitumor activity of the novel dinitroaniline prodrugs/Ssap-NtrB enzyme suicide gene system: Synthesis, in vitro and in silico evaluation in prostate cancer

Prodrugs for targeted tumor therapies have been extensively studied in recent years due to not only maximising therapeutic effects on tumor cells but also reducing or eliminating serious side effects on healthy cells. This strategy uses prodrugs which are safe for normal cells and form toxic metabolites (drugs) after selective reduction by enzymes in tumor tissues. In this study, prodrug candidates (1-36) containing nitro were designed, synthesized and characterized within the scope of chemical experiments. Drug-likeness properties of prodrug candidates were analyzed using DS 2018 to investigate undesired toxicity effects. In vitro cytotoxic effects of prodrug canditates were performed with MTT assay for human hepatoma cells (Hep3B) and prostate cancer cells (PC3) and human umbilical vein endothelial cells (HUVEC) as healthy control. Non-toxic compounds (3, 5, 7, 10, 12, 15, 17, 19 and 21–23), and also compounds (1, 2, 5, 6, 9, 11, 14, 16, 20 and 24) which had low toxic effects, were selected to examine their suitability as prodrug canditates. The reduction profiles and kinetic studies of prodrug/Ssap-NtrB combinations were performed with biochemical analyses. Then, selected prodrug/Ssap-NtrB combinations were applied to prostate cancer cells to determine toxicity. The results of theoretical, in vitro cytotoxic and biochemical studies suggest 14/Ssap-NtrB, 22/Ssap-NtrB and 24/Ssap-NtrB may be potential prodrug/enzyme combinations for nitroreductase (Ntr)-based prostate cancer therapy.

Efficient synthetic route to aromatic secondary amines: Via Pd/RuPhos/TBAB-catalyzed cross coupling

Herein, C-N cross coupling methodology was developed for the synthesis of a diverse range of nitro-substituted secondary amines. A variety of strained, aliphatic, and aromatic precursors were effectively used, with low catalyst and ligand loading ratios resulting in product formation in good yield. This method can act as an alternative to nucleophilic addition reactions. To cross couple electron-donating, electron-withdrawing, neutral, and aliphatic primary amines with alkyl/aryl halides, a combination of RuPhos and TBAB was carefully tuned. Further, characterization of these molecules was carried out using FT-IR, 1H-NMR, 13C-NMR, 19F-NMR, single crystal XRD, and C, H, and N elemental analyses.

Deep Eutectic Solvent/Lipase: Two Environmentally Benign and Recyclable Media for Efficient Synthesis of N-Aryl Amines

Abstract: Deep eutectic solvent (DES)/lipase catalyzed efficient synthesis of N-aryl amines from electron deficient aryl chlorides and amines at ambient temperature is reported. Its significant features include excellent yields of products, use of biodegradable, non-toxic and recyclable catalysts, thereby avoiding toxic metal catalyst/solvents making these protocols environmentally benign. Graphical Abstract: [Figure not available: see fulltext.].

Oxidative arylamination of 1,3-dinitrobenzene and 3-nitropyridine under anaerobic conditions: The dual role of the nitroarenes

1,3-Dinitrobenzene and 3-nitropyridine react with lithium arylamides under anaerobic conditions to produce N-aryl-2,4-dinitroanilines and N-aryl-5-nitropyridin-2-amines, respectively, in 8-42% yields. ARKAT-USA, Inc.

Vicarious nucleophilic substitution of hydrogen in 2,4-dinitroanilines and cyanonitroanilines

Orientation of the VNS reaction in nitroaniline derivatives is mostly governed by the conjugation between the nitro groups and the amino group, which could be also deprotonated under the reaction conditions.