78080-34-9

Usage

Uses

Used in Pharmaceutical Industry:
4-Bromo-N-butylbenzamide is used as a building block for the synthesis of various pharmaceuticals due to its unique structural properties and potential pharmacological activity. It contributes to the development of new drugs with improved therapeutic effects and reduced side effects.
Used in Agrochemical Industry:
4-Bromo-N-butylbenzamide is also used as a building block in the synthesis of agrochemicals, such as pesticides and herbicides. Its structural properties allow for the creation of more effective and environmentally friendly agrochemicals, enhancing crop protection and yield.
Used in Medicinal Chemistry Research:
4-Bromo-N-butylbenzamide serves as a valuable compound for researchers in medicinal chemistry, providing insights into the synthesis and characterization of new drug candidates. Its unique structure and potential pharmacological activity make it a promising subject for further exploration and development in the field of drug design.
Used in Drug Development:
The synthesis and characterization of 4-Bromo-N-butylbenzamide offer valuable information for drug developers, aiding in the discovery and optimization of new therapeutic agents. Its potential applications in medicinal chemistry and drug development make it an essential component in the ongoing pursuit of innovative and effective treatments for various diseases and conditions.

InChI:InChI=1/C11H14BrNO/c1-2-3-8-13-11(14)9-4-6-10(12)7-5-9/h4-7H,2-3,8H2,1H3,(H,13,14)

Upstream product

• 41262-33-3 1-(4-bromophenyl)-2,2,2-trichloroethan-1-one 
• 109-73-9 N-butylamine 
• 586-75-4 4-chlorobenzoyl chloride 
• 1122-91-4 4-bromo-benzaldehyde 
• 586-76-5 4-Bromobenzoic acid 
• 99-90-1 para-bromoacetophenone 
• 201230-82-2 carbon monoxide 
• 66107-30-0 4-bromophenyl trifluoromethanesulfonate 
• 106-41-2 4-bromo-phenol 
• 1380243-00-4 3-(4-bromobenzoyl) oxazolidin-2-one 
• 589-87-7 1,4-bromoiodobenzene 
• 192436-83-2 4-bromo-N-methoxy-N-methylbenzamide 

Relevant academic research and scientific papers

A CO2-Catalyzed Transamidation Reaction

Transamidation reactions are often mediated by reactive substrates in the presence of overstoichiometric activating reagents and/or transition metal catalysts. Here we report the use of CO2as a traceless catalyst: in the presence of catalytic amounts of CO2, transamidation reactions were accelerated with primary, secondary, and tertiary amide donors. Various amine nucleophiles including amino acid derivatives were tolerated, showcasing the utility of transamidation in peptide modification and polymer degradation (e.g., Nylon-6,6). In particular,N,O-dimethylhydroxyl amides (Weinreb amides) displayed a distinct reactivity in the CO2-catalyzed transamidation versus a N2atmosphere. Comparative Hammett studies and kinetic analysis were conducted to elucidate the catalytic activation mechanism of molecular CO2, which was supported by DFT calculations. We attributed the positive effect of CO2in the transamidation reaction to the stabilization of tetrahedral intermediates by covalent binding to the electrophilic CO2

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.

NaOTs-promoted transition metal-free C-N bond cleavage to form C-X (X = N, O, S) bonds

Multifunctional transformation of amide C-N bond cleavage is reported. The protocol applies to benzamide, thioamide, alcohols, and mercaptan under similar reaction conditions catalyzed by NaOTs. It is noteworthy that NaOTs can not only be recycled and reused for up to three cycles without significant loss in catalytic activity, but also catalyze gram-grade reactions. This study provides a novel solution with mild conditions and a simple procedure for transformation of multiple amides.

5-Bromo-norborn-2-en-7-one derivatives as a carbon monoxide source for palladium catalyzed carbonylation reactions

Norbornenone (5b), obtained from the reaction of 2,5-dimethyl-3,4-diphenylcyclopentadienone dimer (3) with bromomaleic anhydride (4b), provides an excellent base-triggered source of carbon monoxide for palladium-catalysed carbonylation reactions. Aminocarbonylation, ketoamide synthesis, and Suzuki-Miyaura reactions of aryl iodides carried out in a two-chamber reaction vessel gave good to excellent yields of carbonylated products.

Broadly Applicable Ytterbium-Catalyzed Esterification, Hydrolysis, and Amidation of Imides

An efficient, broadly applicable, operationally simple, and divergent process for the transformation of imides into a range of carboxylic acid derivatives under mild conditions is reported. By simply using catalytic amounts of ytterbium(III) triflate as a Lewis acid promoter in the presence of alcohols, water, amines, or N,O-dimethylhydroxylamine, a broad range of imides is smoothly and readily converted to the corresponding esters, carboxylic acids, amides, and Weinreb amides in good yields. This method notably enables an easy cleavage of oxazolidinone-based auxiliaries.

Ligand- and Solvent-Tuned Chemoselective Carbonylation of Bromoaryl Triflates

The palladium-catalyzed chemoselective carbonylation of bromoaryl triflates is reported. The selective C?Br bond versus C?OTf (OTf=triflate) bond functionalization can be remarkably tuned by the combination of the ligand [4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) vs. 1,1′-bis(diphenylphosphino)ferrocene (DPPF)] and the solvent (toluene vs. DMSO). The respective ligand and solvent effects are rationalized by DFT calculations. In contrast, the monodentate ligands BuPAd2 and tBu3P prefer the selective C?Br bond activation and are solvent insensitive.

Radical-mediated divergent cyclization of benzamides toward perfluorinated or cyanated isoquinolinediones

A simple and efficient copper-controlled divergent cyclization of benzamides, which leads to perfluorinated or cyanated isoquinolinediones, is developed. In the presence of AIBN, methacryloyl benzamides with perfluoroalkyl iodides undergo cascade radical addition/cyclization to afford perfluoroinated isoquinolinediones as the major product under metal-free conditions, whereas the use of CuI (10 mol%) is able to redirect the cyclization to yield isoquinolinediones bearing an α-cyano quaternary carbon center. The cyclization features controllable divergent synthesis and a broad substrate scope as well as highly practical reaction conditions, thereby making this strategy a highly attractive means to fluorinate or cyanate isoquinolinediones.

N-heterocyclic carbene-catalyzed oxidative amidation of aldehydes with amines

The N-heterocyclic carbene (NHC)-catalyzed oxidative amidation of aromatic aldehydes with amines in the presence of N-bromosuccinimide (NBS) as an oxidant has been developed for the synthesis of amides. This amidation strategy is tolerant to both the electronic and the steric nature of the aryl aldehydes employed. The present methodology was extended to chiral amino acid derivatives to generate the corresponding amides in good yields and excellent ee values (>98%).

Metal free amide synthesis via carbon-carbon bond cleavage

A metal-free oxidative coupling of methyl ketones and primary amines to amides has been developed. The reaction tolerates a variety of functional groups, and is operationally simple. The reaction is proposed to go through a radical pathway to form the triiodomethyl ketone intermediate and the amide is formed by the nucleophilic attack of amine on triiodomethyl ketone carbonyl.

Fluorescent β-cyclodextrins modified by isomeric aminobenzamides: Synthesis, conformational analysis, and fluorescent behaviors

Three isomeric fluorescent β-cyclodextrins bearing 2-, 3-, and 4-(2-aminoethyl)amino-N-butylbenzamide, respectively (1-3) have been synthesized. The conformations of these fluorescent CDs have been investigated by 2D NMR and induced circular dichromism. It is confirmed that the ortho isomer 1 takes a butyl-included conformation, while the other two isomers 2 and 3 display a phenyl-included conformation, respectively. The three fluorescent CDs 1-3 exhibited totally different self- and guest-inclusion fluorescence behavior. In the presence of adamantane carboxylate sodium (ADA) or deoxycholate sodium (DCA), the fluorescence intensity of 1 showed an enhancement over 1-fold, while 2 exhibited dramatic fluorescence quenching. Interestingly, the fluorescent responses of 3 toward two guests respectively were highly distinguishable. The fluorescence intensity of 3 only showed a slight increase upon the addition of ADA, but the addition of DCA led to a large decrease in fluorescence intensity. The investigations have been further carried out by 2D NMR, induced circular dichromism, fluorescence spectroscopy and molecular modeling to explore the relationships between the conformations and the fluorescence characteristics of CDs 1-3 in the absence and presence of guest molecules. On the basis of the above investigations, the origins for the different fluorescence behaviors have been proposed.