6846-12-4

Usage

Uses

Used in Pharmaceutical Industry:
4-Bromo-N-phenylbenzamide is used as a key intermediate in the synthesis of various pharmaceuticals for its potential to contribute to the development of new drug molecules. Its unique structure allows it to be a valuable component in creating medications that address a range of health conditions.
Used in Agrochemical Industry:
In the agrochemical sector, 4-Bromo-N-phenylbenzamide is utilized as an intermediate in the production of agrochemicals, playing a crucial role in the development of pesticides, herbicides, and other agricultural products that enhance crop protection and yield.
Used in Organic Synthesis:
4-Bromo-N-phenylbenzamide is used as a building block in organic synthesis, enabling the creation of a wide array of organic compounds for various applications across different industries, from pharmaceuticals to materials science.
Used as a Reagent in Chemical Reactions:
4-Bromo-N-phenylbenzamide also serves as a reagent in a variety of chemical reactions, facilitating processes that lead to the formation of desired products in research and industrial applications, further highlighting its versatility and importance in the field of chemistry.

InChI:InChI=1/C13H10BrNO/c14-11-8-6-10(7-9-11)13(16)15-12-4-2-1-3-5-12/h1-9H,(H,15,16)

Upstream product

• 586-76-5 4-Bromobenzoic acid 
• 28098-93-3 4-bromo-benzophenone-(Z)-hydrazone 
• 98556-16-2 4-bromo-thiobenzoic acid 
• 103-72-0 phenyl isothiocyanate 
• 1122-91-4 4-bromo-benzaldehyde 
• 62-53-3 aniline 
• 586-75-4 4-chlorobenzoyl chloride 
• 6048-21-1 4-bromobenzoyl cyanide 
• 110-00-9 furan 
• 72730-68-8 C-(4-bromobenzoyl)-N-phenylnitrone 
• 67-56-1 methanol 
• 107590-73-8 N-phenyl-N'-<1-phenyl-1-(4-bromobenzoyl)-2,2,2-trifluoroethyl>carbodiimide 
• 64-17-5 ethanol 
• 118364-54-8 N-(1-phenyl-2,2,2-trifluoroethylidene)-N'-4-bromobenzoyl-N'-phenylurea 

Downstream Products

• 105728-76-5 (4-bromophenyl)[4-(dimethylamino)phenyl]methanone 
• 93-98-1 N-phenyl benzoyl amide 
• 68695-50-1 4-bromo-N-phenylbenzimidoyl chloride 
• 3164-13-4 2-(4-bromophenyl)-1,3-benzoxazole 
• 1253388-63-4 C₂₇H₁₈BrNO 
• 1256360-84-5 C₂₃H₁₈BrNO₃ 
• 1256360-83-4 C₂₄H₂₁NO₄ 
• 586-76-5 4-Bromobenzoic acid 
• 62-53-3 aniline 
• 540466-42-0 2-(4-bromo-phenyl)-4-phenyl-quinazoline 
• 19654-19-4 2-(4-bromophenyl)benzothiazole 
• 6911-90-6 N-phenyl 4-bromobenzothioamide 
• 127580-92-1 (4-bromophenyl)(morpholino)methanone 
• 301228-28-4 4-bromo-N-(2-(trifluoromethyl)phenyl)benzamide 

Relevant academic research and scientific papers

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.

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.

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.

A practical and sustainable protocol for direct amidation of unactivated esters under transition-metal-free and solvent-free conditions

In this paper, a NaOtBu-mediated synthesis approach was developed for direct amidation of unactivated esters with amines under transition-metal-free and solvent-free conditions, affording a series of amides in good to excellent yields at room temperature. In particular, an environmentally friendly and practical workup procedure, which circumvents the use of organic solvents and chromatography in most cases, was disclosed. Moreover, the gram-scale production of representative products3a,3wand3auwas efficiently realized by applying operationally simple, sustainable and practical procedures. Furthermore, this approach was also applicable to the synthesis of valuable molecules such as moclobemide (a powerful antidepressant), benodanil and fenfuram (two commercial agricultural fungicides). These results demonstrate that this protocol has the potential to streamline amide synthesis in industry. Meanwhile, quantitative green metrics of all the target products were evaluated, implying that the present protocol is advantageous over the reported ones in terms of environmental friendliness and sustainability. Finally, additional experiments and computational calculations were carried out to elucidate the mechanistic insight of this transformation, and one plausible mechanism was provided on the basis of these results and the related literature reports.

Acetyl nitrate mediated conversion of methyl ketones to diverse carboxylic acid derivatives

The development of a novel acetyl nitrate mediated oxidative conversion of methyl ketones to carboxylic acid derivatives is described. By analogy to the haloform reaction and supported by experimental and computational investigation we propose a mechanism for this transformation.

Iron-catalyzed oxidative amidation of acylhydrazines with amines

A new approach for amide bond formation via a mild and efficient Iron-catalyzed cross-coupling reaction of acylhydrazines and amines using TBHP as oxidant is described. This protocol is compatible with a wide range of amines and acylhydrazines. In addition, the synthetic application of the reaction is presented.

Selective hydrogenation dehalogenation method of ortho-halogenated acylaniline

The invention discloses a selective hydrogenation dehalogenation method of copper-catalyzed ortho-halogenated acylaniline. The method comprises the following steps: by using ortho-halogenated acylaniline as a starting raw material and copper acetylacetonate/vasicine as a catalyst, adding an organic alkali, reacting in an alcoholic solution at 80-100 DEG C for 12 hours, and regioselectively catalytically hydrogenating ortho-bromine and iodine atoms. The preparation method has the characteristics of simplicity and convenience in operation, wide substrate application range, low cost, high regioselectivity and the like, and has practicability.

Exploration of Cu-catalyzed regioselective hydrodehalogenation of o-haloanilides using EtOH as hydrogen source

In present work, we have explored a Cu(acac)2/vasicine-catalyzed regioselective hydrodehalogenation methodology of o-haloanilides using EtOH as hydrogen source and solvent. The catalytic system could selectively dehalogenate 2-Br and 2-I, and features regioselective, efficient and functional group tolerance.

Activated charcoal supported copper nanoparticles: A readily available and inexpensive heterogeneous catalyst for the N-arylation of primary amides and lactams with aryl iodides

A novel heterogeneous copper catalyst has been developed by supporting copper nanoparticles on activated charcoal via in situ reducing copper(II) with aqueous hydrazine as reductant. The characterization of Cu/C catalyst showed that the Cu0 nano-particles were formed on the surface of charcoal. This catalyst displayed good catalytic activities toward the N-arylation of primary amides and lactams with aryl iodides.

α-Imino Iridium Carbenes from Imidoyl Sulfoxonium Ylides: Application in the One-Step Synthesis of Indoles

Imidoyl sulfoxonium ylides are presented for the first time as potential precursors to generate α-imino metal-carbene intermediates and applied in direct C-H functionalization reactions catalyzed by [Ir(cod)Cl]2 (4 mol %) to provide 2-substituted indoles (up to 70% yield) in just one step. This class of sulfur ylide is successfully obtained from imidoyl chloride and dimethylsulfoxonium methylide (23 new examples in 45-85% yield) or by imino group formation from the corresponding β-keto sulfoxonium ylides and anilines in the presence of TiCl4 as a Lewis acid (9 examples in 33-94% yield).