1945-92-2

Usage

Uses

Used in Dye and Pigment Production:
2,4-DINITRO-N-(2-HYDROXYETHYL)ANILINE is used as a key intermediate in the synthesis of various dyes and pigments, contributing to the coloration and stability of these products in different industries.
Used in Pharmaceutical Synthesis:
As an intermediate, 2,4-DINITRO-N-(2-HYDROXYETHYL)ANILINE plays a crucial role in the development of pharmaceuticals, aiding in the creation of new drugs and enhancing existing ones.
Used in Azo Dye Synthesis:
2,4-DINITRO-N-(2-HYDROXYETHYL)ANILINE is an important precursor in the synthesis of azo dyes, which are widely used in various applications due to their colorfast properties.
Used as a Reagent in Organic Synthesis:
In the field of organic chemistry, 2,4-DINITRO-N-(2-HYDROXYETHYL)ANILINE serves as a reagent, facilitating various chemical reactions and contributing to the synthesis of a range of organic compounds.
Used in Research and Development:
In the scientific community, 2,4-DINITRO-N-(2-HYDROXYETHYL)ANILINE is utilized in research and development for exploring new chemical pathways and understanding the properties of related compounds.

InChI:InChI=1/C8H9N3O5/c12-4-3-9-7-2-1-6(10(13)14)5-8(7)11(15)16/h1-2,5,9,12H,3-4H2

Upstream product

• 70-34-8 2,4-Dinitrofluorobenzene 
• 141-43-5 ethanolamine 
• 584-48-5 2,4-dinitrobromobenzene 
• 60-29-7 diethyl ether 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 64-17-5 ethanol 
• 13181-22-1 O-(2',4'-dinitrophenyl) 1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one oxime 
• 154853-46-0 2,4-dinitrophenyl 4-methoxybenzenesulfonate 
• 101219-76-5 2-(methylthio)ethyl 2,4-dinitrophenyl ether 
• 67674-33-3 2,4-dinitrophenyl 2-methoxyethyl ether 
• 89-02-1 2,4-dinitrobenzenesulfonic acid 
• 18226-13-6 N-(2,4-dinitrobenzenesulfonyl)ethanolamine 
• 709-49-9 1-iodo-2,4-dinitrobenzene 

Downstream Products

• 56932-44-6 1-(2'-hydroxy-ethyl)amino-2-amino-4-nitro-benzene 
• 4481-55-4 N-(2-hydroxyethyl)-N-(2',4',6'-trinitrophenyl)nitramine nitrate 
• 16830-65-2 N-(2-chloroethyl)-2,4-dinitrobenzenamine 
• 23920-12-9 N-(2-methoxy-ethyl)-2,4-dinitro-aniline 
• 1263363-91-2 3',5'-di-O-acetyl-2'-deoxy-O₆-{2-[(2,4-dinitophenyl)amino]ethyl}guanosine 
• 1245006-61-4 2,4-dinitro-N-(2-(prop-2-ynyloxy)ethyl)aniline 
• 57944-32-8 N¹-(2-chloro-ethyl)-4-nitro-o-phenylenediamine 
• 56223-91-7 N’-(2,4-dinitrophenyl)-N,N-diethylethane-1,2-diamine 
• 5099-39-8 N⁽¹⁾-(2-(diethylamino)ethyl)-4-nitrobenzene-1,2-diamine 
• 97-02-9 2,4-Dinitroanilin 
• 51-28-5 2,4-Dinitrophenol 
• 2871-01-4 1-[(2-hydroxyethyl)amino]-2-nitro-4-aminobenzene 

Relevant academic research and scientific papers

The mechanism of aromatic nucleophilic substitution reaction between ethanolamine and fluoro-nitrobenzenes: An investigation by kinetic measurements and DFT calculations

We have studied the kinetics and elucidated the mechanism by DFT calculation of the reaction between ethanolamine (EOA) and 1-fluoro-2,4- dinitrobenzene (DNFB) in acetonitrile and toluene. To determine the contribution of the nitro group, the activation energy of the reaction between ethanolamine and 1-fluoro-2-nitrobenzene (MNFB) vs. DNFB was determined in acetonitrile and calculated by DFT method. Kinetic measurements reveal that the reaction is faster in acetonitrile than in toluene. The reaction follows overall second-order kinetics: first order with respect to both EOA and DNFB which is similar to the results reported for reaction between other primary amines and 1-substituted-2,4-dinitrobenzenes. The calculations by using DFT methods reveal that the mechanism of the reaction involves the formation and decomposition of a Meisenheimer complex (MC). DFT calculations also reveal that the activation energy of the reaction is highest in vacuum and decreases with increasing polarity of the solvent reaching a minimum in acetonitrile. In addition, activation energies obtained by both DFT calculations and experiments show that the reactivity of MNFB is less than that of DNFB showing the effect of the 4-nitro group.

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.

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.

Nucleotides. Part LXXVIII: Double labeling of nucleosides and nucleotides

Several N(-hydroxyalkyl)-2,4-dinitroanilines were transformed into their phosphoramidites (see 5 and 6 in Scheme 1) in view of their use as fluorescence quenchers, and modified 2-aminobenzamides (see 9, 10, 18, and 19 in Scheme 1) were applied in model re

Aryl-containing esters of triphosphoric acid as substrates of terminal deoxynucleotidyl transferase

A new group of terminal deoxynucleotidyltransferase (TDT) substrates, namely, non-nucleoside triphosphates (NNTP) bearing 5-substituted 2,4-dinitrophenyl fragments instead of nucleoside residues was synthesized. Copyright Taylor & Francis Group, LLC.

Kinetic studies on the reactions of O-(2′,4′-dinitrophenyl) 1,7,7-trimethylbicyclo[2.2.1]heptan-2-one oxime with nucleophiles in aprotic solvents - Mechanism for the uncatalysed pathway

Kinetics of the reactions of the title compound with some amines as nucleophiles in aprotic solvents have been investigated at the λmax of the aminolysis product at 35 ± 0.1 °C under pseudo-first order conditions. The reaction is overall second order, first with respect to each reactant. The second order rate coefficients decreased with increase in [amine] in all cases. Formation of an electron donor-acceptor complex is indicated. The temperature effect on the reaction rate has been studied in the range (293-318 K). The entropy of activation parameters are large and negative in all cases indicating formation of a crowded transition state. Mechanistic interpretation is given.

Effect of substituent on regioselectivity and reaction mechanism in aminolysis of 2,4-dinitrophenyl X-substituted benzenesulfonates

(Chemical Equation Presented) We report on a kinetic study for the nucleophilic substitution reactions of 2,4-dinitrophenyl X-substituted benzensulfonates (X = 4-MeO, 1a, and X = 4-NO2, 1c) with a series of primary amines in 80 mol % H2O/20 mol % DMSO at 25.0 °C. The reactions proceed through S-O and C-O bond fission pathways competitively. The fraction of the S-O bond fission increases as the attaching amine becomes more basic and the substituent X changes from 4-MeO to 4-NO2, indicating that the regioselectivity is governed by the electronic nature of the substituent X as well as the basicity of amines. The S-O bond fission has been suggested to proceed through an addition intermediate with a change in the rate-determining step (RDS) at pK°a = 8.9 ± 0.1. The electronic nature of the substituent X influences kNS-O and k1 values, but not the k2/k-1 ratios and the pK°a value significantly. Stabilization of the ground state (GS) through resonance interaction between the electron-donating substituent and the electrophilic center has been suggested to be responsible for the decreased reactivity of 1a compared to 1c. The second-order rate constants for the C-O bond fission exhibit no correlation with the electronic nature of the substituent X. The distance effect and the nature of the reaction mechanism have been suggested to be responsible for the absence of the correlation.

Kinetics of reactions of o-(2,4-dinitrophenyl)indanone oxime with cyclohexylamine, piperidine and ethanolamine in acetonitrile

Effect of nucleophile on the reactions of o-(2,4-dinitrophenyl) indanone oxime (DNPIO) has been studied with cyclohexylamine (CHA), ethanolamine (ETA) and piperidine (PIP) in acetonitrile at 35±0.1°C. Reactions of DNPIO with CHA and ETA are kinetically of second order. However, the reactions with PIP are wholly base catalyzed and a third order dependence on PIP has been observed.

Unusual reaction of 1,4-diamino-2-nitrobenzene derivatives toward nucleophiles: Catalysis by sodium sulphite

Unusual substitution of amino group occurs by reactions of some 1,4diamino-2-nitrobenzenes (semipermanent hair dyes) and nucleophiles (NH3, H2O). The reaction is catalyzed by sodium sulfite. The obtained products are suspected of being toxic substances which may be present in cosmetic matrices. Apparently, this reaction is a nucleophilic aromatic substitution but it may be explained by a mechanism involving a tautomeric form of substrate.