13059-84-2

Upstream product

• 107-10-8 propylamine 
• 584-48-5 2,4-dinitrobromobenzene 
• 54718-72-8 (2,4-dinitrophenyl)dipropylamine 
• 70-34-8 2,4-Dinitrofluorobenzene 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 13181-75-4 O-(2,4-dinitrophenyl) cyclohexanone oxime 
• 13181-14-1 1-phenylethan-1-one O-(2,4-dinitrophenyl) oxime 
• 17188-67-9 diphenylmethanone O-(2,4-dinitrophenyl)oxime 
• 115806-86-5 O-(2,4-dinitrophenyl)-4'-bromobenzophenone oxime 
• 75-04-7 ethylamine 
• 109-73-9 N-butylamine 
• 74-89-5 methylamine 
• 108-18-9 diisopropylamine 
• 107-08-4 1-iodo-propane 

Downstream Products

• 51625-37-7 2,4,6,N-tetranitro-N-propyl-aniline 
• 66668-43-7 N¹-n-propyl-4-nitro-benzene-1,2-diamine 

Relevant academic research and scientific papers

Synthesis, aerobic cytotoxicity, and radiosensitizing activity of novel 2,4-dinitrophenylamine tethered 5-fluorouracil and hydroxyurea

Two novel dual functional agents, 3[3-(2,4-dinitro-phenylamino)-propyl]-5-fluoro-1H-pyrimidine-2,4-dione 7 and N-[3-(2,4-dinitro-phenylamino)-propoxy]urea 8, resulting from linkage of 2,4-dinitrophenylamine through three carbon atoms with 5-fluorouracil 5

KINETIC STUDIES AND MICELLAR EFFECT ON THE AMINOLYSIS OF CERTAIN O-ARYL OXIMES

Rate constants for the aminolysis of a few O-aryl oximes with several primary alkyl amines, CH3NH2-------C6H12NH2 in 1:1 water-acetonitrile are reported.Reactions of methylamine with substrates possessing poor nucleofugues are very weakly sensitive to base catalysis while reactions of higher amines are not.Slightly higher rate of long chain amine may be considered as a consequence of hydrophobic interaction.Cationic micelles of cetyltrimethyl ammonium bromide enhance the rate.Magnitude of micellar catalysis increases towards higher amines.

Mechanistic assessment of SNAr displacement of halides from 1-Halo-2,4-dinitrobenzenes by selected primary and secondary amines: Br?nsted and Mayr analyses

Pseudo-first-order rate constants (kobsd) have been measured spectrophotometrically for nucleophilic substitution reactions of 1-X-2,4-dinitrobenzenes (1a-d, X = F, Cl, Br, I) with various primary and secondary amines in MeCN and H2O

Effect of the nature of the nucleophile and solvent on an SNAr reaction

The reaction of 2,4-dinitrobenzenesulfonyl chloride toward propylamine was kinetically evaluated in 19 organic solvents and 10 ionic liquids as reaction media. This study was compared with a previous study to experimentally show that solvent effects and t

Low background FRET-substrates for lipases and esterases suitable for high-throughput screening under basic (pH 11) conditions

FRET-based fluorogenic substrates for lipases and esterases were prepared in four steps from commercially available building blocks. The substrates are pyrenebutyric acid monoesters of aliphatic 1,2-diols bearing a dinitrophenylamino group as a quencher. The most enzyme-reactive substrate is ester 2a. The substrates do not show any measurable background reaction in the absence of enzyme even at pH 11, but react fast and specifically with lipases and esterases. These substrates offer an unprecedented and practical solution to the long-standing problem of a simple yet efficient high-throughput screening tool for lipase activities under basic conditions. The Royal Society of Chemistry 2006.

RETRACTED ARTICLE: Sanger's Reagent Sensitized Photocleavage of Amide Bond for Constructing Photocages and Regulation of Biological Functions

Photolabile groups offer promising tools to study biological processes with high spatial and temporal control. In the investigation, we designed and prepared several new glycine amide derivatives of Sanger's reagent and demonstrated that they serve as a new class of photocages for Zn2+ and an acetylcholinesterase (AChE) inhibitor. We showed that the mechanism for photocleavage of these substances involves initial light-driven cyclization between the 2,4-dinitrophenyl and glycine methylene groups to form acyl benzimidazole N-oxides, which undergo secondary photoinduced decarboxylation in association with rupture of an amide bond. The cleavage reactions proceed with modest to high quantum yields. We demonstrated that these derivatives can be used in targeted intracellular delivery of Zn2+, fluorescent imaging by light-triggered Zn2+ release, and regulation of biological processes including the enzymatic activity of carbonic anhydrase (CA), negative regulation of N-methyl-d-aspartate receptors (NMDARs), and pulse rate of cardiomyocytes. The successful proof-of-concept examples described above open a new avenue for using Sanger's reagent-based glycine amides as photocages for the exploration of complex cellular functions and signaling pathways.

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.

“Zero VOC” Synthetic Strategy – Aromatic Amination Reactions in Deep Eutectic Solvents

Rising concern for environment hazards resulting from the use of volatile organic compounds (VOCs) is prompting many chemists to use “green” solvents like water, polyethylene glycol, ionic liquids and deep eutectic solvents (DES). With a few notable exceptions, many of these processes still need to use volatile organic solvents for the workup and isolation of products. In the present report, we demonstrate a “zero VOC” protocol which eliminates the need to use organic solvents for any stage of the reaction. As a proof of concept, nucleophilic aromatic substitution reactions of 1-halo-2,4-dinitrobenzene with secondary amines were carried out in deep eutectic solvents. The reaction workup involved the addition of water for separating the product from the DES. Evaporation of water led to recovery of the DES, which exhibited good recyclability. The reaction in deep eutectic solvents was much faster than that in many other solvents, as confirmed by the kinetic studies. An attempt was made to elucidate the origin of this rate enhancement based on analysis activation parameters and correlation with the polarity parameters. The results show that use of deep eutectic solvents can take chemists a step closer towards the “zero VOC” synthetic strategy.

The influence of steric effects on the kinetics and mechanism of SNAr reactions of 1-phenoxy-nitrobenzenes with aliphatic primary amines in acetonitrile

Rate constants are reported for the reactions of 1-phenoxy-dinitrobenzenes, 3, 1-phenoxy-dinitrotrifluoromethylbenzenes, 4, with n-propylamine, and 1-methylheptylamine in acetonitrile as solvent. The results are compared with results reported previously f

Specific nucleophile-electrophile interactions in nucleophilic aromatic substitutions

We herein report results obtained from an integrated experimental and theoretical study on aromatic nucleophilic substitution (SNAr) reactions of a series of amines towards 1-fluoro-2,4-dinitrobenzene in water. Specific nucleophile-electrophile interactions in the title reactions have been kinetically evaluated. The whole series undergoes SNAr reactions where the formation of the Meisenheimer complex is rate determining. Theoretical studies concerning specific interactions are discussed in detail. It is found that H-bonding effects along the intrinsic reaction coordinate profile promote the activation of both the electrophile and the nucleophile. Using these results, it is possible to establish a hierarchy of reactivity that is in agreement with the experimental data. Second order energy perturbation energy analysis highlights the strong interaction between the ortho-nitro group and the acidic hydrogen atom of the amine. The present study strongly suggests that any theoretical analysis must be performed at the activated transition state structure, because the static model developed around the reactant states hides most of the relevant specific interactions that characterize the aromatic substitution process.