39242-76-7

Usage

InChI:InChI=1/C10H11N3O5/c14-12(15)8-1-2-9(10(7-8)13(16)17)11-3-5-18-6-4-11/h1-2,7H,3-6H2

Upstream product

• 110-91-8 morpholine 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 92-53-5 4-Phenylmorpholine 
• 2486-07-9 2,4-dinitrophenyl phenyl ether 
• 17188-67-9 diphenylmethanone O-(2,4-dinitrophenyl)oxime 
• 70-34-8 2,4-Dinitrofluorobenzene 
• 139643-73-5 2,3-<3-norcaren-endo-2,5-diyl>-N-(2',4'-dinitrophenoxy)succinimide 
• 896-80-0 1-benzenesulfonyl-2,4-dinitro-benzene 
• 899-02-5 (2,4-dinitro-phenyl)-p-tolyl sulfone 
• 899-03-6 (4-chloro-phenyl)-(2,4-dinitro-phenyl)-sulfone 
• 972-48-5 1-(2,4-dinitro-benzenesulfonyl)-4-methoxy-benzene 
• 1098-16-4 (2,4-dinitro-phenyl)-(4-nitro-phenyl)-sulfone 
• 75317-05-4 (4-bromo-phenyl)-(2,4-dinitro-phenyl)-sulfone 
• 99-65-0 meta-dinitrobenzene 

Downstream Products

• 110-91-8 morpholine 
• 51-28-5 2,4-Dinitrophenol 
• 5367-65-7 4-morpholin-4-yl-3-nitro-aniline 
• 4031-79-2 2-Morpholino-5-nitro-anilin 
• 110210-14-5 4-(2,4-dinitrophenoxy)morpholine 
• 13272-46-3 2,4-bis-acetylamino-1-morpholin-4-yl-benzene 

Relevant academic research and scientific papers

Aromatic nucleophilic substitution (snar) reactions of halo-substituted dinitrobenzene in liposome reaction media: Effect of reaction medium and role of halogen leaving group

SNAr reactions constitute an important pathway for the synthesis of many crucial organic derivatives from polyhaloaromatic compounds. The sluggish nature of the reaction in many cases makes it a challenging pathway and limits its potential appl

Iso-solvation effects in mixtures of ionic liquids on the kinetics of a model SNAr reaction

The SNAr reaction between 1-chloro-2,4-dinitrobenzene and morpholine was used as a model system to study solvation effects in a series of mixtures involving imidazolium based ionic liquids. Iso-solvation regimes (i.e. a solvent composition regi

Mechanism of Aromatic Nucleophilic Substitution in Aprotic Solvents

The effect of various hydrogen-bond acceptors on the reactions of 1-chloro- and 1-fluoro-2,4-dinitrobenzenes with morpholine in benzene at 30 deg C has been investigated.The reaction of the chloro substrate is not base-catalysed and the additives produced

Kinetic and equilibrium studies of σ-adduct formation and nucleophilic substitution in the reactions of morpholine with 1,3,5-trinitrobenzene and some phenyl aryl ethers in dimethyl sulphoxide

Reactions of morpholine in dimethyl sulphoxide at unsubstituted ring positions of 1,3,5-trinitrobenzene, and phenyl 2,4,6-trinitrophenyl ether, yield anionic σ-adducts via zwitterionic intermediates. Reactions at the 1-position of phenyl 2,4,6-trinitrophe

Gutmann's Donor Numbers Correctly Assess the Effect of the Solvent on the Kinetics of SNAr Reactions in Ionic Liquids

We report an experimental study on the effect of solvents on the model SNAr reaction between 1-chloro-2,4-dinitrobenzene and morpholine in a series of pure ionic liquids (IL). A significant catalytic effect is observed with reference to the sam

Changes in the SNAr reaction mechanism brought about by preferential solvation

We herein report an experimental and theoretical study on preferential solvation effects for the reactions of 1-fluoro and 1-chloro-2,4-dinitrobenzene towards morpholine in acetonitrile, water and mixtures of them of varying compositions. A detailed kinet

Photoredox catalyzed dealkylative aromatic halogen substitution with tertiary amines

A reaction of aromatic halides bearing electron-withdrawing groups with tertiary amines in the presence of an iridium catalyst under blue light irradiation is described. Products of the aromatic substitution of the halide by the dialkylamino fragment are

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.

Aryl-Diadamantyl Phosphine Ligands in Palladium-Catalyzed Cross-Coupling Reactions: Synthesis, Structural Analysis, and Application

Synthesis, temperature-dependent NMR structure investigation and utilization of a new, stable and easily accessible aryl-diadamantylphosphine ligand family is reported. The bulky and electron-rich phosphorus center of the ligand enhances the catalytic activity of palladium in cross-coupling reactions of sterically demanding ortho-substituted aryl halides. In our study, we demonstrated the synthetic applicability of the new phosphine ligands in Buchwald-Hartwig and tosyl hydrazone coupling reactions.

Decarboxylative ipso Amination of Activated Benzoic Acids

In the presence of a bimetallic Pd/Cu system with 1,10-phenanthroline as the ligand and either air or N-methylmorpholine N-oxide as the oxidant, electron-deficient benzoic acids undergo oxidative decarboxylative coupling with unprotected amines. This operationally simple aniline synthesis is widely applicable with respect to the amine and gives good yields, even on multigram scale. The orthogonality of this reaction to other Pd-catalyzed cross-couplings allows the concise synthesis of multisubstituted arenes by sequential C?C, C?Cl, and C?N functionalizations. Mechanistic investigations suggest the intermediacy of a hypervalent Pd species.