7403-38-5

Usage

InChI:InChI=1/C13H11N3O4/c17-15(18)11-6-7-12(13(8-11)16(19)20)14-9-10-4-2-1-3-5-10/h1-8,14H,9H2

Upstream product

• 70-34-8 2,4-Dinitrofluorobenzene 
• 100-46-9 benzylamine 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 584-48-5 2,4-dinitrobromobenzene 
• 65052-88-2 N,N-dibenzyl-2,4-dinitro-aniline 
• 64-19-7 acetic acid 
• 970-88-7 2,4-dinitrophenyl benzenesulfonate 
• 742-25-6 2,4-dinitrophenyl 4-methylbenzenesulfonate 
• 973-63-7 2,4-dinitrophenyl 4-chlorobenzenesulfonate 
• 758640-21-0 N-Benzylaniline 
• 89-02-1 2,4-dinitrobenzenesulfonic acid 
• 100-52-7 benzaldehyde 
• 97-02-9 2,4-Dinitroanilin 
• 709-49-9 1-iodo-2,4-dinitrobenzene 

Downstream Products

• 95711-95-8 N,2,4,6-Tetranitro-N-(4-nitrobenzyl)-anilin 
• 66108-86-9 N¹-benzyl-4-nitro-o-phenylenediamine 
• 303149-18-0 2-[(6-nitro-2-phenyl-1H-1,3-benzimidazol-1-yl)oxy]acetic acid 
• 10066-14-5 6-nitro-2-phenyl-benzoimidazol-1-ol 

Relevant academic research and scientific papers

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.

Synthesis of N-Substituted 3-Amino-4-halopyridines: A Sequential Boc-Removal/Reductive Amination Mediated by Br?nsted and Lewis Acids

N-Substituted 3-amino-4-halopyridines are valuable synthetic intermediates, as they readily provide access to imidazopyridines and similar heterocyclic systems. The direct synthesis of N-substituted 3-amino-4-halopyridines is problematic, as reductive aminations and base-promoted alkylations are difficult in these systems. A high yielding deprotection/alkylation protocol mediated by trifluoroacetic acid and trimethylsilyl trifluoromethanesulfonate is described, providing access to a wide scope of N-substituted 3-amino-4-halopyridines. This protocol furnishes many reaction products in high purity without chromatography. Similar reductive amination conditions were also established for deactivated anilines.

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.

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.

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

Design, synthesis, and evaluation of thiol-activated sources of sulfur dioxide (SO2) as antimycobacterial agents

Here, 2,4-dinitrophenylsulfonamides with tunable cysteine-activated SO 2 release profiles with half-lives of SO2 release varying from 2 to 63 min are reported. N-Benzyl-2,4-dinitrobenzenesulfonamide (6), which is prepared in one step

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.

Palladium-catalyzed N-heteroannulation of N-allyl- or N-benzyl-2-nitrobenzenamines: synthesis of 2-substituted benzimidazoles

A palladium-catalyzed reductive N-heteroannulation of N-allyl- or N-benzyl-2-nitrobenzenamines, using carbon monoxide as the ultimate reducing agent, affording 2-substituted benzimidazoles has been developed.

Novel anti-infection agents: Small-molecule inhibitors of bacterial transcription factors

Structure-based drug design was utilized to identify potent small-molecule inhibitors of proteins within the AraC family of bacterial transcription factors, which control virulence in medically important microbes. These agents represent a novel approach to fight infectious disease and may be less likely to promote resistance development. These compounds lack intrinsic antibacterial activity in vitro and were able to limit a bacterial infection in a mouse model of urinary tract infection.

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.