2585-26-4

Usage

Uses

Used in Pharmaceutical Industry:
N-benzyl-4-nitrobenzamide is utilized as an intermediate in the synthesis of various drugs and pharmaceuticals. Its unique structure and functional groups make it a valuable component in the development of new medications.
Used in Organic Synthesis:
N-benzyl-4-nitrobenzamide serves as a key building block in organic synthesis, enabling the creation of a variety of complex organic molecules for various applications.
Used as a Reagent in Chemical Research:
N-benzyl-4-nitrobenzamide is employed as a reagent in chemical research, facilitating the study of chemical reactions and the development of novel synthetic methods.
Used in Antimicrobial and Antifungal Applications:
N-benzyl-4-nitrobenzamide has been studied for its potential biological activities, including its antimicrobial and antifungal properties. This makes it a promising candidate for use in the development of new antimicrobial and antifungal agents to combat resistant strains and infections.

InChI:InChI=1/C14H12N2O3/c17-14(15-10-11-4-2-1-3-5-11)12-6-8-13(9-7-12)16(18)19/h1-9H,10H2,(H,15,17)

Upstream product

• 854846-60-9 2-methyl-3-(4-nitrobenzoyl)-4H-chromen-4-one 
• 100-46-9 benzylamine 
• 122-04-3 4-nitro-benzoyl chloride 
• 58547-64-1 (4-Nitro-benzoylsulfanyl)-acetic acid 
• 62-23-7 4-nitro-benzoic acid 
• 25105-62-8 2-benzyl-3-(4-nitro-phenyl)-oxaziridine 
• 50903-08-7 N-benzyl-4-nitrothiobenzamide 
• 4231-71-4 1H-1,2,3-benzotriazol-1-yl-4-nitrophenylmethanone 
• 555-16-8 4-nitrobenzaldehdye 
• 636-98-6 p-nitrobenzene iodide 
• 201230-82-2 carbon monoxide 
• 619-73-8 4-nitrobenzyl chloride 
• 66049-46-5 2-(p-nitrobenzoyloxy)-2-cyclohexen-1-one 
• 619-80-7 4-nitrobenzamide 

Downstream Products

• 92164-89-1 4-Nitro-benzoesaeure-<4-nitro-benzylamid> 
• 54977-92-3 4-amino-N-(benzyl)benzamide 
• 80318-54-3 N-(4'-nitrobenzoyl)-4-hydroxybenzylamine 
• 80311-93-9 N-(Hydroxybenzyl)-4-nitrobenzamide 
• 62-23-7 4-nitro-benzoic acid 
• 3712-57-0 N-(benzyl)-4-nitrobenzimidoyl chloride 
• 876893-51-5 N-[(1H-1,2,3-benzotriazol-1-yl)(4-nitrophenyl)methylidene]-N-benzylamine 
• 100-52-7 benzaldehyde 
• 619-80-7 4-nitrobenzamide 
• 14429-16-4 benzyl(4-nitrobenzyl)amine 
• 272786-89-7 diethyl (4-nitrophenyl)-N-(benzyl)aminomethylphosphonate 
• 3712-57-0 N-benzyl-4-nitrobenzimidoyl chloride 
• 1430730-42-9 4-benzyl-5-(4-nitrophenyl)-3-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-1,2,4-triazole 
• 1430730-58-7 4-Benzyl-5-(β-D-glucopyranosyl)-3-(4-nitrophenyl)-1,2,4-triazole 

Relevant academic research and scientific papers

Acyl Transfer from S-Monoacyldihydrolipoamide to Benzylamine in the Presence of Oxidizing Agents

Acyl transfer reaction from N-benzyl-8-S-(p-nitrobenzoyl)dihydrolipoamide to benzylamine was enhanced with oxidizing agents such as cobalt(II) ion or a soluble flavin under an oxygen atmosphere or with di-4-pyridyl disulfide, accompanied by the formation

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.

Amide Bond Formation via the Rearrangement of Nitrile Imines Derived from N-2-Nitrophenyl Hydrazonyl Bromides

We report how the rearrangement of highly reactive nitrile imines derived from N-2-nitrophenyl hydrazonyl bromides can be harnessed for the facile construction of amide bonds. This amidation reaction was found to be widely applicable to the synthesis of primary, secondary, and tertiary amides and was used as the key step in the synthesis of the lipid-lowering agent bezafibrate. The orthogonality and functional group tolerance of this approach was exemplified by the N-acylation of unprotected amino acids.

Chemoselective Hydrogenation of Nitroarenes Using an Air-Stable Base-Metal Catalyst

The reduction of nitroarenes to anilines as well as azobenzenes to hydrazobenzenes using a single base-metal catalyst is reported. The hydrogenation reactions are performed with an air-and moisture-stable manganese catalyst and proceed under relatively mild reaction conditions. The transformation tolerates a broad range of functional groups, affording aniline derivatives and hydrazobenzenes in high yields. Mechanistic studies suggest that the reaction proceeds via a bifunctional activation involving metal-ligand cooperative catalysis.

Photochemical Activation of Aromatic Aldehydes: Synthesis of Amides, Hydroxamic Acids and Esters

A cheap, facile and metal-free photochemical protocol for the activation of aromatic aldehydes has been developed. Utilizing thioxanthen-9-one as the photocatalyst and cheap household lamps as the light source, a variety of aromatic aldehydes have been activated and subsequently converted in a one-pot reaction into amides, hydroxamic acids and esters in good to high yields. The applicability of this method was highlighted in the synthesis of Moclobemide, a drug against depression and social anxiety. Extended and detailed mechanistic studies have been conducted, in order to determine a plausible mechanism for the reaction.

Crystal structure of 1-(2,4,6-trichlorobenzoyloxy) benzotriazole (TCB-OBt): observation of uncommon intermolecular oxygen-oxygen interaction and synthetic application in amidation

Herein, we investigated the supramolecular assembly of a modified Yamaguchi reagent TCB-OBt. Interestingly, each molecule is interconnected through novel chalcogen-chalcogen (O?O) interaction, π-π stacking, and aromatic C-H?O interaction. Hirshfeld surface analysis confirmed the existence of uncommon O?O interactions. A well-organized supramolecular layer structure and helical arrangement were observed in the crystal structure. TCB-OBt crystallized in the O-substituted desmotropic form. DFT calculations suggest that the O-substituted form is more stable than theN-substituted form (TCB-(N)-OBt). Morphology analysis indicates the formation of a fantastically well organized, continuous block-shaped system. Furthermore, the designed reagent works as an efficient activating reagent for amide bond formation with good yields under mild reaction conditions. Use of this reagent avoided intractable acid chlorides, and this new mixed-anhydride-based reagent may further be applicable for many other organic transformations.

Br?nsted Acid Mediated Nucleophilic Functionalization of Amides through Stable Amide C?N Bond Cleavage; One-Step Synthesis of 2-Substituted Benzothiazoles

We have developed a Br?nsted acid mediated synthetic method to directly cleave stable amide C?N bonds by a variety of alcohol and amine nucleophiles. Reverse reactivity was observed and alcoholysis of amides by activated primary and secondary benzylic, and propargylic alcohols have been achieved instead of the expected nucleophilic substitution of alcohols. As an application, 2-substituted benzothiazole derivatives have been synthesized in one pot employing 2-aminothiophenol as nucleophile.

Efficient and accessible silane-mediated direct amide coupling of carboxylic acids and amines

A straightforward method for the direct synthesis of amides from amines and carboxylic acids without exclusion of air or moisture using diphenylsilane with N-methylpyrrolidine has been developed. Various amides are made efficiently, and broad functional group compatibility is shown through a Glorius robustness study. A gram-scale synthesis demonstrates the scalability of this method. This journal is

Ammonia-borane as a Catalyst for the Direct Amidation of Carboxylic Acids

Ammonia-borane serves as an efficient substoichiometric (10%) precatalyst for the direct amidation of both aromatic and aliphatic carboxylic acids. In situ generation of amine-boranes precedes the amidation and, unlike the amidation with stoichiometric amine-boranes, this process is facile with 1 equiv of the acid. This methodology has high functional group tolerance and chromatography-free purification but is not amenable for esterification. The latter feature has been exploited to prepare hydroxyl- and thiol-containing amides.

Graphene oxide: A convenient metal-free carbocatalyst for facilitating amidation of esters with amines

Herein, we report a graphene oxide (GO) catalyzed condensation of non-activated esters and amines, that can enable diverse amides to be synthesized from abundant ethyl esters forming only volatile alcohol as a by-product. GO accelerates ester to amide conversion in the absence of any additives, unlike other catalysts. A wide range of ester and amine substrates are screened to yield the respective amides in good to excellent yields. The improved catalytic activity can be ascribed to the oxygenated functionalities present on the graphene oxide surface which forms H-bonding with the reactants accelerating the reaction. Improved yields and a wide range of functional group tolerance are some of the important features of the developed protocol.