970-76-3

Basic information

• Product Name: 2,4-dinitro-N-(4-nitrophenyl)aniline
• Synonyms: 2,4-dinitro-N-(4-nitrophenyl)aniline;4-Nitrophenyl(2,4-dinitrophenyl)amine
• CAS NO: 970-76-3
• Molecular Formula: C₁₂H₈N₄O₆
• Molecular Weight: 304.21512
• EINECS: 213-536-7
• Mol File: 970-76-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 491.1°Cat760mmHg
• Flash Point: 250.8°C
• Appearance: /
• Density: 1.592g/cm³
• Vapor Pressure: 8.62E-10mmHg at 25°C
• Refractive Index: 1.717
• CAS DataBase Reference: 2,4-dinitro-N-(4-nitrophenyl)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-dinitro-N-(4-nitrophenyl)aniline(970-76-3)
• EPA Substance Registry System: 2,4-dinitro-N-(4-nitrophenyl)aniline(970-76-3)

Safety Data

• Hazardous Substances Data: 970-76-3(Hazardous Substances Data)

Usage

General Description

2,4-dinitro-N-(4-nitrophenyl)aniline is a chemical compound with the molecular formula C12H7N5O6. It is a bright yellow crystalline solid with no distinct odor. 2,4-dinitro-N-(4-nitrophenyl)aniline is used primarily in the production of dyes, pigments, and pharmaceuticals. It is considered to be toxic and can cause irritation to the skin, eyes, and respiratory system. Additionally, it is classified as a potential carcinogen and can be harmful if ingested or inhaled. Due to its potential health hazards, proper handling and disposal procedures are necessary when working with this chemical.

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 
• 836-30-6 4-ntrophenyl(phenyl)amine 
• 99-65-0 meta-dinitrobenzene 
• 586-96-9 Nitrosobenzene 
• 88-74-4 2-nitro-aniline 
• 103859-52-5 (2-nitro-phenyl)-(4-nitroso-phenyl)-amine 
• 7697-37-2 nitric acid 

Downstream Products

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

Relevant articles and documents

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.

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.