3846-50-2

Usage

Uses

Used in Pharmaceutical Industry:
2,4-DINITRO-N-ETHYLANILINE is used as a key compound in the synthesis of novel dinitroaniline prodrugs with antitumor activity. These prodrugs are specifically designed for nitroreductase-based prostate cancer therapy, targeting and treating cancer cells more effectively.
2,4-DINITRO-N-ETHYLANILINE's role in the development of these prodrugs lies in its ability to be activated by nitroreductase enzymes, which are overexpressed in certain cancer cells. Upon activation, the prodrug releases a toxic agent that can inhibit the growth and proliferation of cancer cells, making it a valuable tool in the fight against prostate cancer.

InChI:InChI=1/C8H9N3O4/c1-2-9-7-4-3-6(10(12)13)5-8(7)11(14)15/h3-5,9H,2H2,1H3

Upstream product

• 529-65-7 N-ethylacetanilide 
• 10112-15-9 N-Ethyl-2-nitroaniline 
• 5429-28-7 4-(diethylamino)benzoic acid 
• 837-64-9 N,N-diethyl-2,4-dinitroaniline 
• 2788-74-1 4-(ethylamino)-3-nitrobenzoic acid 
• 857596-68-0 N-ethyl-2,4-dinitro-N-nitroso-aniline 
• 584-48-5 2,4-dinitrobromobenzene 
• 75-04-7 ethylamine 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 64-17-5 ethanol 
• 509-14-8 tetranitromethane 
• 64-19-7 acetic acid 
• 56269-48-8 N-ethyl-N-methyl-4-nitrobenzeneamine 
• 80800-12-0 N-ethyl-2,4-dinitroacetanilide 

Downstream Products

• 66668-41-5 N¹-ethyl-4-nitro-benzene-1,2-diamine 
• 6052-13-7 N-nitro-N-ethyl-2,4,6-trinitroaniline 
• 857596-68-0 N-ethyl-2,4-dinitro-N-nitroso-aniline 
• 51-28-5 2,4-Dinitrophenol 
• 75-04-7 ethylamine 
• 1370363-72-6 5-amino-2-(p-bromophenyl)-1-ethyl-benzimidazol 
• 90349-15-8 1-ethyl-5-nitro-1H-benzo[d]imidazole 
• 223745-04-8 5-amino-N-ethylbenzimidazolone 
• 58533-62-3 5-nitro-N-ethylbenzimidazolone 
• 202279-57-0 2,4-diamino-N-ethylaniline 
• 74180-10-2 N-(2,4-Dinitro)phenyl-N'-ethyl-N-methylbenzamidine 

Relevant academic research and scientific papers

Cobalt-based molecular electrocatalysis of nitrile reduction: Evolving sustainability beyond hydrogen

Two new cobalt bis-iminopyridines, [Co(DDP)(H2O)2](NO3)2 (1, DDP = cis-[1,3-bis(2-pyridinylenamine)] cyclohexane) and [Co(cis-DDOP)(NO3)](NO3) (2, cis-DDOP = cis-3,5-bis[(2-Pyridinyleneamin]-trans-hydroxycyclohexane) electrocatalyse the 4-proton, 4-electron reduction of acetonitrile to ethylamine. For 1, this reduction occurs in preference to reduction of protons to H2. A coordinating hydroxyl proton relay in 2 reduces the yield of ethylamine and biases the catalytic system back towards H2.

5-amino-N-substituted benzimidazolone synthetic method

The invention discloses a synthesis method of 5-amonio-N-substituted benzimidazolone. The synthesis method is characterized by comprising the following steps of: (1) dropwise adding amine to an alcohol solvent of 2,4-dinitrochlorobenzene at a room temperature to be reacted for 0.5 hour to 2hours at a backflow temperature, and recrystallizing a product to obtain an N-substituted phenylamine; and (2), adding N-substituted phenylamine, sulphur, dimethylformamide, ammonium formate and potassium carbonate into water in a high-pressure reaction kettle to be reacted for 2 hours to 5hours under the condition of 160 to 200 DEG C, cooling the product to the room temperature, releasing the pressure to the atmospheric pressure, adding hydrazine hydrate and active carbon catalyst loaded with metal salt, heating to 60 to 100 DEG C to be reacted for 2 hours to 3hours, thermally filtering the product, steaming and drying the solvent, and recrystallizing the product to obtain the 5-amonio-N-substituted benzimidazolone. The reaction route is short, the reaction is simple, and the yield of the prepared product is high.

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.

Design and synthesis of positional isomers of 1-alkyl-2-trifluoromethyl-5 or 6-substituted benzimidazoles and their antimicrobial activity

A series of novel positional isomers of 1-alkyl-2-trifluoromethyl benzimidazole derivatives 3a-j and 4a-j have been synthesized and screened for antibacterial activity against gram positive bacteria viz, Bacillus subtilis, Staphylococcus aureus and gram negative bacteria viz., Escherichia coli, Pseudomonas aeruginosa and antifungal activity against Candida albicans, Aspergillus niger, Rhizopus oryzae and Saccharomyces cerevisiae. Results indicate that compounds 3b, 4b were having promising antibacterial and antifungal activity.

Synthesis, characterization of some novel benzimidazole derivatives of 1-bromo-2, 4-dinitrobenzene and their antifungal activities

Six novel benzimidazole derivatives, 5-nitro-2-phenyl -1-ethyl benzimidazol (5), 2- (ρ -bromophenyl)- 5-nitro- 1-ethyl benzimidazol (6), 2- (ρ-bromophenyl-5-nitro-1-cyclopentyl benzimidazol (7), 2- (ρ-bromophenyl)-5-nitro-1-cyclopentyl benzimidazol (8), 5-amino-2-(ρ- bromophenyl)-1- ethylbenzimidazol (9) and 5-amino-2-(ρ-bromophenyl)-1- cyclopentyl benzimidazol(10) were synthesized . The structures of all the synthesized compounds were elucidated by using elemental analysis and different spectroscopic techniques(IR, NMR and mass spectroscopy). Some of these compounds showed potential antifungal activities. The biological activity of these compounds as fungicides was tested against Candida albicans, patient isolate Candida labrata and Candida krusei. The biological activity of four compounds was found to be comparable to that of the commercially available fungicides with a inimum inhibitory concentration of 12.5 μ.

Synthesis of (alkylamino)nitroarenes by oxidative alkylamination of nitroarenes

The viability of the oxidative alkylamination process for the derivatization of electron-deficient carboaromatics has been investigated. 1,3-Dinitrobenzene, 1-nitronaphthalene, and 1,5- and 1,8-dinitronaphthalenes have shown to react with a wide range of alkylamines in the presence of an oxidant (KMnO4, AgMnO4, AgPy2MnO4) to give access to the corre sponding N-alkyl-nitroarenamines in moderate to good yields. Nitroarenes are more reactive than azines towards alkylamines.

Nucleophilic and acid catalyst behavior of a protic ionic liquid in a molecular reaction media. Part 1

This work presents a new approach using ionic liquids, namely ethylammonium nitrate. The aim was to analyze how the addition of small amounts of a protic ionic liquid to a pure molecular solvent, modifies the microscopic characteristics of a reaction medium. In order to achieve this, a kinetic study of nucleophilic aromatic substitution reactions between 1-fluoro-2, 4-dinitrobenzene and 1-butylamine or piperidine was developed in this type of binary mixtures. We have detected nucleophiles competition originated by the presence of the ionic solvent at very low concentrations, observing the ethylamine derivative as the main substitution product. Moreover, in the light of previous results we have confirmed that the protic ionic liquid can act as both Broensted acid and/or nucleophile. In this connection, we have selected the nucleophilic addition of amines to carbonyl compounds as reaction model. The protic ionic liquid in the presence of aromatic aldehydes substituted by electron-donating groups makes possible the formation of the corresponding imines with good yields. The results demonstrated that the influence of the protic ionic liquid is very important in the course of both reaction systems. Copyright

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.

Synthesis and magnetic properties of new binuclear Cu(II) complexes with tridentate azomethine ligands

New binuclear copper complexes of tridentate azomethine ligands with various combinations of N, O, and S donor centers were prepared by various procedures, including template synthesis. The magnetochemical data obtained for the range 2-300 K suggest the occurrence of antiferromagnetic coupling in most of these chelates. The only exception is the complex containing N-tosyl and N-ethyl donor fragments, in which the ferromagnetic exchange is observed. Nauka/Interperiodica 2006.