3393-96-2

Usage

Uses

Used in Research and Development:
4'-NITROBENZANILIDE is used as a chemical intermediate for the synthesis of various complex compounds. It plays a crucial role in the development of new chemical entities and the advancement of scientific research.
Used in Pharmaceutical Industry:
4'-NITROBENZANILIDE is used as a building block in the synthesis of pharmaceutical compounds. Its unique structure allows for the creation of new drug candidates with potential therapeutic applications.
Used in Chemical Synthesis:
4'-NITROBENZANILIDE is used as a reagent in various chemical reactions, enabling the formation of new compounds with different properties and applications.
Used in Material Science:
4'-NITROBENZANILIDE is used in the development of new materials with specific properties, such as improved stability or enhanced reactivity, for various industrial applications.

InChI:InChI=1/C13H10N2O3/c16-13(10-4-2-1-3-5-10)14-11-6-8-12(9-7-11)15(17)18/h1-9H,(H,14,16)

Upstream product

• 64-19-7 acetic acid 
• 4702-72-1 benzil mono(p-nitrophenylhydrazone) 
• 100-01-6 4-nitro-aniline 
• 93-97-0 benzoic acid anhydride 
• 785-81-9 4-nitro-N-(phenylmethylene)benzenamine 
• 18039-42-4 5-Phenyl-1H-tetrazole 
• 98-88-4 benzoyl chloride 
• 456-27-9 4-nitrobenzenediazonium tetrafluoroborate 
• 100-28-7 4-Nitrophenyl isocyanate 
• 65-85-0 benzoic acid 
• 15873-51-5 4-nitroaniline hydrochloride 
• 83728-51-2 N-Cyclopentyl-N'-(4-nitro-phenyl)-pyridine-2-carboxamidine 
• 613-94-5 benzoic acid hydrazide 
• 76540-09-5 N-(4-Nitro-phenyl)-N-(pyridine-2-carbonyl)-benzamide 

Downstream Products

• 17625-83-1 N-(4-aminophenyl)benzamide 
• 5265-19-0 N-(4-nitrophenyl)thiobenzamide 
• 13296-94-1 2-bromo-4-nitroaniline 
• 34918-79-1 N-(4-nitro-phenyl)-benzimidoyl chloride 
• 55-21-0 benzamide 
• 100-01-6 4-nitro-aniline 
• 100990-64-5 N-benzoyl-2-(N-benzoyl)amino-5,4'-dinitrodiphenylamine 
• 1775-95-7 2-amino-5-nitrobenzophenone 
• 41214-79-3 N-(2,4-dinitrophenyl)benzamide 
• 65-85-0 benzoic acid 
• 33672-82-1 N-(4-nitrophenyl)-N-methylbenzamide 
• 1045325-34-5 C₁₄H₁₃N₅O₂S 
• 1131896-96-2 C₂₁H₁₈N₄O₂S₂ 
• 1131897-02-3 C₁₉H₁₅N₃O₂S 

Relevant academic research and scientific papers

Use of halomethyl resins to immobilize amines: An efficient method for synthesis of sulfonamides and amides on a solid support

Methods for the synthesis of chloromethyl and bromomethyl equivalents of Wang's resin are described. To explore the utility of this acid clearable resin, amines were immobilized through the nitrogen atom, further functionalized, and then cleaved under acid conditions.

TBAI-catalyzed C–N bond formation through oxidative coupling of benzyl bromides with amines: a new avenue to the synthesis of amides

A new green approach for the synthesis of amide through TBAI-catalyzed oxidative coupling of benzyl bromides with amine was developed in the presence of tert-butyl hydroperoxide (TBHP) as an oxidant. Various electron-donating and withdrawing groups containing benzyl bromides and various amines, were subjected to the reaction and transformed to the corresponding amide in good to excellent yields.

Visible-light-induced direct construction of amide bond from carboxylic acids with amines in aqueous solution

A novel visible-light-promoted N-acylation for the synthesis of amides from easily available carboxylic acids with amines in the presence of I2 within 2.5 h in aqueous solution has been developed. Using sunlight as the visible light source greatly reduces the cost of experiments and produces almost no toxic effects. Hence, this study provides an alternative catalytic system for the construction of a wide range of amides with readily available materials. Moreover, the strategy was successfully applied in the preparation of N-(3-(2,6-dimethoxyphenoxy)-7-nitroquinoxalin-2-yl)benzohydrazide, which displayed a signification anti-proliferation effect on A549, MCF-7 and HCT116 cell lines.

Synthesis of ring-opened derivatives of triazole-containing quinolinones and their antidepressant and anticonvulsant activities

Based on the potent antidepressant and anticonvulsant activities of the triazole-containing quinolinones reported in our previous work, a series of ring-opened derivatives of them were designed, synthesized in this work. Their antidepressant and anticonvulsant activities were screened using the forced swimming test (FST) and the maximal electroshock seizure test (MES), respectively. The results showed that compounds 4a, 5a, 6c-6e, 6g-6i, and 7 led to significant reductions in the accumulated immobility time in the FST at a dose of 50 mg/kg. Especially compound 7 exhibited higher levels of efficacy than the reference standard fluoxetine in the FST and the tail suspension test. The results of an open field test excluded the possibility of central nervous stimulation of 7, which further confirmed its antidepressant effect. Meanwhile, compounds 6a-6i and 7 showed different degrees of anticonvulsant activity in mice at the doses range from 300 to 30 mg/kg in the MES. Among them, compounds 6e and 7 displayed the ED50 of 38.5 and 32.7 mg/kg in the MES, and TD50 of 254.6 and 245.5 mg/kg, respectively. No one showed neurotoxicity at the dose of 100 mg/kg. The preliminary investigation forward to their mechanism indicated that regulation of GABAergic system might contribute to their anticonvulsive and anti-depressive action.

Visible-Light Carbon Nitride-Catalyzed Aerobic Cyclization of Thiobenzanilides under Ambient Air Conditions

A metal-free heterogeneous photocatalysis has been developed for the synthesis of benzothiazoles via intramolecular C-H functionalization/C-S bond formation of thiobenzanilides by inexpensive graphitic carbon nitride (g-C3N4) under visible-light irradiation. This reaction provides access to a broad range of 2-substituted benzothiazoles in high yields under an air atmosphere at room temperature without addition of a strong base or organic oxidizing reagents. In addition, the catalyst was found to be stable and reusable after five reaction cycles.

Carboxylic Acid Deoxyfluorination and One-Pot Amide Bond Formation Using Pentafluoropyridine (PFP)

This work describes the application of pentafluoropyridine (PFP), a cheap commercially available reagent, in the deoxyfluorination of carboxylic acids to acyl fluorides. The acyl fluorides can be formed from a range of acids under mild conditions. We also demonstrate that PFP can be utilized in a one-pot amide bond formation via in situ generation of acyl fluorides. This one-pot deoxyfluorination amide bond-forming reaction gives ready access to amides in yields of ≤94%.

Visible-Light-Promoted Iron-Catalyzed N-Arylation of Dioxazolones with Arylboronic Acids

A visible-light-promoted and simple iron salt-catalyzed N-arylation was achieved efficiently under external photosensitizer-free conditions. Arylboronic acids and bench-stable dioxazolones were used for this cross-coupling reaction. This reaction features high reactivity, wide substrate scope, good functional group tolerance, simple operation procedure, and mild reaction conditions. Preliminary mechanistic investigations were conducted to support a radical pathway. This method may contribute to shift the paradigm of iron-catalyzed C-N bond construction and nitrene transfer chemistry.

An Environmentally Benign, Catalyst-Free N?C Bond Cleavage/Formation of Primary, Secondary, and Tertiary Unactivated Amides

Herein, we report an operationally simple, cheap, and catalyst-free method for the transamidation of a diverse range of unactivated amides furnishing the desired products in excellent yields. This protocol is environmentally friendly and operates under extremely mild conditions without using any promoter or additives. Significantly, this strategy has been implied in the chemoselective synthesis of a pharmaceutical molecule, paracetamol, on a gram-scale with excellent yield. We anticipate that this universally applicable strategy will be of great interest in drug discovery, biochemistry, and organic synthesis.

Regioselective Synthesis of 2° Amides Using Visible-Light-Induced Photoredox-Catalyzed Nonaqueous Oxidative C-N Cleavage of N, N-Dibenzylanilines

A visible-light-driven photoredox-catalyzed nonaqueous oxidative C-N cleavage of N,N-dibenzylanilines to 2° amides is reported. Further, we have applied this protocol on 2-(dibenzylamino)benzamide to afford quinazolinones with (NH4)2S2O8 as an additive. Mechanistic studies imply that the reaction might undergo in situ generation of α-amino radical to imine by C-N bond cleavage followed by the addition of superoxide ion to form amides.

Co2(CO)8as a Solid CO (g) Source for the Amino Carbonylation of (Hetero)aryl Halides with Highly Deactivated (Hetero)arylamines

Carbonylation of (hetero)aryl iodides/bromides with highly deactivated 2-aminopyridines using Pd-Co(CO)4 bimetallic catalysis is accomplished. The use of Co2(CO)8 as a solid CO(g) source enhanced reaction rates observed when compared to CO(g), and excellent yields highlight the versatility of the developed protocol. A wide range of electronically and sterically demanding heterocyclic amines and (hetero)aryl iodides/bromides employed for this study resulted in excellent yields of amino carbonylated products. The developed methodology was further extended to synthesize Trypanosome brucie and luciferase inhibitors.