13059-85-3

Usage

Uses

Used in Agricultural Industry:
2,4-dinitro-N-(propan-2-yl)aniline is used as a pre-emergence herbicide for controlling grasses and broadleaf weeds in a variety of crops. It is effective in managing unwanted plant growth, ensuring the healthy development of desired crops and increasing agricultural productivity.
Safety Precautions:
When using and handling 2,4-dinitro-N-(propan-2-yl)aniline, it is crucial to follow proper safety protocols to prevent potential health risks. This includes wearing appropriate personal protective equipment, such as gloves, goggles, and masks, to minimize exposure to the eyes, skin, and respiratory system. Additionally, it is important to store the chemical in a secure and well-ventilated area, away from direct sunlight and heat sources, to maintain its stability and effectiveness.

Upstream product

• 584-48-5 2,4-dinitrobromobenzene 
• 75-31-0 isopropylamine 
• 1195-42-2 N-cyclohexylisopropylamine 
• 75008-95-6 5-amino-1-(2,4-dinitrophenyl)-1H-pyrazole-4-carbonitrile 
• 768-52-5 N-Isopropylaniline 
• 67-63-0 isopropyl alcohol 
• 97-02-9 2,4-Dinitroanilin 
• 108-18-9 diisopropylamine 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 70-34-8 2,4-Dinitrofluorobenzene 

Downstream Products

• 1315307-65-3 1-isopropyl-5-nitro-1,3-dihydro-2H-benzimidazol-2-one 
• 56136-70-0 N¹-isopropyl-4-nitrobenzene-1,2-diamine 

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.

Hofmann N-alkylation of aniline derivatives with alcohols using ferric perchlorate immobilized on SiO2 as a catalyst through Box–Behnken experimental design

An efficient method for the N-alkylation of poorly nucleophilic amines using ferric perchlorate immobilized on SiO2 as a catalyst is described. Fe(ClO4)3 was prepared from mixing iron(III) hydroxide and perchloric acid and adsorbed on silica gel. The catalyst was characterized using various techniques. The supported ferric perchlorate (Fe(ClO4)3/SiO2) revealed high efficiency and selectivity for N-alkylation of aromatic amines with alcohols to provide alkylated amines. Various secondary amines were synthesized from primary amines and alcohols in good to excellent yields, with water as the only by-product. The optimization of the reaction conditions was investigated using the response surface method, and involving the Box–Behnken design matrix. The conditions for optimal reaction yield and time were: amount of catalyst?=?0.34?mmol, temperature?=?60°C and molar ratio of amine to alcohol?=?1.2. The catalyst was recovered and reused for five cycles without a considerable decrease in catalytic activity. The stability of the recycled catalyst was investigated. The proposed method has numerous advantages including procedure simplicity, short reaction times, low cost, good to excellent yields, reusability of the catalyst and mild and environmentally benign conditions.

BICYCLICALLY SUBSTITUTED URACILS AND THE USE THEREOF

The present application relates to novel bicyclically substituted uracil derivatives, to processes for preparation thereof, to the use thereof alone or in combinations for treatment and/or prophylaxis of diseases, and to the use thereof for production of medicaments for treatment and/or prophylaxis of diseases.

Pd(OAc)2-catalyzed dinitration reaction of aromatic amines

Taking advantage of Pd(OAc)2-catalyzed dinitration reactions with Bi(NO3)3·5H2O in trifluoroethanol (TFE) and trifluoroacetic acid (TFA), we have developed an efficient and practical method for the synthesis of secondary dinitro-aromatic amines. The products could be applied to the preparation of 5-amine-N-methyl-benzimidazolone, the azo-dyes, economic advantages. The method has also been expanded to the dinitration reaction of some tertiary aromatic amines.

Synthesis and biological activity of splitomicin analogs targeted at human NAD+-dependent histone deacetylases (sirtuins)

Small molecules interfering with posttranslational modification of histones are of interest as tools to study epigenetic regulation of gene transcription. Specifically, drugs that interfere with histone deacetylation could be useful to induce differentiation, growth arrest as well as apoptotic cell death in tumor cells. One class of histone deacetylases is known as sirtuins some of which (Saccharomyces cerevisiae Sir2) are for example inhibited by the lactone splitomicin leading to telomeric silencing in yeast. However, splitomicin is only a micromolar inhibitor of yeast Sir2 and does not inhibit human subtypes and the lactone is prone to hydrolytic ring opening. In preliminary SAR-studies, splitomicin analogs lacking this hydrolytically labile ring were described as inactive while the naphthalene moiety could successfully be replaced by smaller aromatic rings in a fragment-like dihydrocoumarin. Here we report the synthesis and biological activity of a series of hydrolytically stable analogs with activity against human SIRT1 and 2. These comparatively small compounds characterized by high ligand efficiency are used as a starting point toward the development of specific inhibitors of histone deacetylases from the class of sirtuins.

A new leaving group in nucleophilic aromatic substitution reactions (S NAr)

Nucleophilic aromatic substitution of a 2,4-dinitrophenyl substituted pyrazole 1 with primary amines leads to substitution of the pyrazolo substituent. In these nucleophilic aromatic substitution reactions (S NAr), 5-amino-1H-4- pyrazolecarbonitrile (3) acts as a new leaving group.

UNUSUAL DEALKYLATIONS AND REARRANGEMENTS IN AROMATIC NUCLEOPHILIC SUBSTITUTION

The reaction of 2,4-dinitrohalobenzenes with di-isopropylamine produces mainly N-(2,4-dinitrophenyl)-isopropylamine and N-(2,4-dinitrophenyl)-n-propylamine instead of the expected straightforward substitution product.Dealkylations are also observed in the reactions with isopropylcyclohexylamine and dicyclohexylamine.A carbanionic mechanism is proposed.

The Stabilities of Meisenheimer Complexes. Part 22. The Ionisation of 2,4-Dinitroaniline, its N-Alkylated Derivatives, and 2,6-Dinitroaniline in Methanol-Dimethyl Sulphoxide containing Sodium Methoxide

2,4-Dinitroaniline and its N-alkylated derivatives react with sodium methoxide in methanol-dimethyl sulphoxide to give conjugate base.However, in the case of 2,6-dinitroaniline, base addition at the 3-position competes with proton loss.The effects of N-alkylation on the acidity of 2,4-dinitroaniline are considered and are compared with the effects of similar substitution in 2,4,6-trinitroaniline.