839-93-0

Usage

Uses

Used in Organic Synthesis:
1-(2,4-dinitrophenyl)piperidine is used as a reactant in the formation of various compounds, contributing to the development of new chemical entities and materials.
Used in Pharmaceutical Industry:
1-(2,4-dinitrophenyl)piperidine is used as a precursor for the production of polypeptide-based antimicrobial agents, playing a crucial role in the development of novel antimicrobial therapies to combat drug-resistant infections.
Used in Research and Diagnostics:
1-(2,4-dinitrophenyl)piperidine is utilized as a reagent for the detection and quantification of proteins and peptides, aiding in the advancement of research and diagnostic tools in the life sciences and biotechnology fields.

InChI:InChI=1/C11H13N3O4/c15-13(16)9-4-5-10(11(8-9)14(17)18)12-6-2-1-3-7-12/h4-5,8H,1-3,6-7H2

Upstream product

• 110-89-4 piperidine 
• 2363-25-9 1-(4-methylphenoxy)-2,4-dinitrobenzene 
• 73901-01-6 2,4-dinitrobenzenesulfonamide 
• 742-25-6 2,4-dinitrophenyl 4-methylbenzenesulfonate 
• 858259-47-9 1-[(2,4-dinitrophenyl)sulfonyl]piperidine 
• 6282-16-2 (2,4-dinitro-phenyl)-(4-methyl-2-nitro-phenyl)-ether 
• 859777-16-5 (4-bromo-2-chloro-5-nitro-phenyl)-(2,4-dinitro-phenyl)-ether 
• 876477-08-6 (2,4-dibromo-5-nitro-phenyl)-(2,4-dinitro-phenyl)-ether 
• 859077-22-8 (2,4-dinitro-phenyl)-(2,4,6-trichloro-3-nitro-phenyl)-ether 
• 859775-76-1 (2,6-dibromo-4-chloro-3-nitro-phenyl)-(2,4-dinitro-phenyl)-ether 
• 859077-17-1 (2,4-dinitro-phenyl)-(2,4,6-tribromo-3-nitro-phenyl)-ether 
• 408349-30-4 (2,4-dinitro-phenyl)-(4-methyl-2,3-dinitro-phenyl)-ether 
• 70-34-8 2,4-Dinitrofluorobenzene 
• 97-00-7 1-chloro-2,4-dinitro-benzene 

Downstream Products

• 5367-60-2 3-nitro-(4-piperidin-1-yl)aniline 
• 5367-58-8 5-nitro-2-(piperidin-1-yl)aniline 
• 51-28-5 2,4-Dinitrophenol 
• 97-02-9 2,4-Dinitroanilin 
• 5367-41-9 N-(3-nitro-4-piperidin-1-yl-phenyl)-acetamide 
• 110210-07-6 N-(2,4-dinitrophenyl)piperidine N-oxide 
• 110210-11-2 1-(2,4-dinitrophenoxy)piperidine 
• 110-89-4 piperidine 
• 2044-88-4 N-methyl-2,4-dinitroaniline 

Relevant academic research and scientific papers

Dimethyl sulfoxide/deep eutectic solvents mixtures as media in the reaction of 1-fluoro-2,4-dinitrobenzene with piperidine: A solvent effect study

Aromatic nucleophilic substitution reaction of 1-fluoro-2,4-dinitrobenzene with piperidine was kinetically investigated in ethylene glycol-choline chloride and glycerol-choline chloride as 2 deep eutectic solvents (DESs) mixed with dimethyl sulfoxide, in

Influence of Anionic and Cationic Reverse Micelles on Nucleophilic Aromatic Substitution Reaction between 1-Fluoro-2,4-dinitrobenzene and Piperidine

The nucleophilic aromatic substitution (SNAr) reaction between 1-fluoro-2,4-dinitrobenzene and piperidine (PIP) were studied in two different reverse micellar interfaces: benzene/sodium 1,4-bis(2-ethylhexyl) sulfosuccinate (AOT)/water and benze

Binary mixtures of dimethyl sulfoxide with methanol, ethylene glycol, and glycerol as solvent: Solvatochromism and chemical kinetics study

The understanding of solvent effects on chemical reaction requires precise knowledge of solute-solvent interactions. Since solute-solvent interactions are much more complex in mixed solvents, the study of chemical kinetics can be valuable because of the p

Solvent dependent leaving group fluorine kinetic isotope effect in a nucleophilic aromatic substitution reaction

Fluorine kinetic isotope effects (F KIEs) have been determined using the accelerator-produced short-lived radionuclide 18F in combination with natural 19F. The solvent dependence of the leaving group F KIE was investigated for the nu

Non-aqueous reverse micelles media for the SNAr reaction between 1-fluoro-2,4-dinitrobenzene and piperidine

The kinetics of the nucleophilic aromatic substitution (SNAr) reaction between 1-fluoro-2,4-dinitrobenzene (FDNB) and piperidine (PIP) in ethylene glycol (EG)/ sodium bis (2-ethyl-1-hexyl) sulfosuccinate (AOT)/n-heptane and dimethylformamide (D

Mechanistic pathways of aromatic nucleophilic substitution in conventional solvents and ionic liquids

Solvation effects on the reaction mechanism of the title reactions have been kinetically evaluated in 21 conventional solvents and 17 ionic liquids. Solvent polarity affects the catalyzed and non-catalyzed SNAr pathways differently. The ambiphi

Dual-parameter correlations on rate of an aromatic nucleophilic substitution reaction in aqueous solutions of methanol, ethanol, and propan-2-ol

Reaction kinetics of 1-chloro-2,4-dinitrobenzene with piperidine was studied spectrophotometrically in aqueous solutions of methanol, ethanol, and propan-2-ol at 25 °C. The reaction in these solutions is not catalyzed by piperidine. The plots of second-order rate constants of the reaction vs. mole fraction of water show maxima in the all-aqueous solutions. Single-parameter correlations of log k2 vs. π* (dipolarity/polarizability), α (hydrogen-bond donor acidity), and ETN (normalized polarity parameter) are very poor in the all solutions (for example, in aqueous solutions of ethanol, regression coefficients are 0.814, 0.113, and 0.486, respectively). Dual-parameter correlations of log k2 vs. π* and α in all cases represent significant improvement with regard to the single-parameter models (in aqueous solutions of ethanol: n = 11, r = 0.980, and s = 0.034). Dipolarity/polarizability and hydrogen-bond donor acidity (HBD) of media have opposite effects on the reaction rate. The activated complex leading to the zwitterionic intermediate is expected to be favored by increasing the solvent dipolarity/polarizability parameter. Increasing the hydrogen-bond donor acidity of solvent stabilizes piperidine and hence the reaction rate decreases. A dual-parameter equation of log k2 vs. π* and α was obtained in the all-aqueous solutions (n = 31, r = 0.956, s = 0.055) in which π* and α have approximately equal and opposite effects on the reaction rate.

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.

Synthesis of o-Nitroarylamines via Ipso Nucleophilic Substitution of Sulfonic Acids

A mild, efficient, and eco-friendly method for the synthesis of o-nitroarylamine from o-nitroaryl sulfonic acid via ipso nucleophilic aryl substitution by amine is described. The products have been obtained with good yields at room temperature without the assistance of any metal, activating agent, or toxic oxidant. This method is useful for racemization-free synthesis of N-aryl amino acid esters.

Overcoming solid handling issues in continuous flow substitution reactions through ionic liquid formation

Substitutions such as acylations, arylations, and alkylations are some of the most commonly run reactions for building complex molecules. However, the requirement of a stoichiometric base to scavange acid by-products creates significant challenges when operating in continuous flow due to solid handling issues associated with precipitating base·HX salts. We present a general and simple strategy to overcome these solid handling issues through the use of acid scavenging organic bases that generate low- to moderate-melting ionic liquids upon protonation. The application of these bases towards the most commonly run substitutions are demonstrated, enabling reactions to be run in flow without requiring additional equipment, specific solvents, or dilute reaction conditions to prevent clogging.