5436-83-9

Usage

Uses

Used in Organic Synthesis:
N-benzyl-4-methyl-benzamide is used as a key intermediate for the synthesis of various organic compounds. Its amide group and aromatic structure make it a versatile building block in the creation of complex organic molecules.
Used in Pharmaceuticals:
In the pharmaceutical industry, N-benzyl-4-methyl-benzamide is utilized as a starting material or intermediate in the development of new drugs. Its unique chemical properties allow it to be modified and functionalized to create potential therapeutic agents.
Used in Agrochemicals:
N-benzyl-4-methyl-benzamide is also employed in the agrochemical sector as a raw material for the production of various pesticides and other agricultural chemicals. Its chemical structure can be tailored to target specific pests or enhance the effectiveness of existing products.
Used in Dyestuff:
In the dyestuff industry, N-benzyl-4-methyl-benzamide is used as a precursor for the synthesis of various dyes and pigments. Its aromatic nature and amide functionality contribute to the color properties and stability of the resulting dyes.

InChI:InChI=1/C15H15NO/c1-12-7-9-14(10-8-12)15(17)16-11-13-5-3-2-4-6-13/h2-10H,11H2,1H3,(H,16,17)

Upstream product

• 26218-73-5 3,4-bis(4-methylphenyl)-1,2,5-oxadiazole-N-oxide 
• 100-46-9 benzylamine 
• 99-94-5 p-Toluic acid 
• 110-82-7 cyclohexane 
• 22693-32-9 4-methylbenzoyl azide 
• 201230-82-2 carbon monoxide 
• 780-25-6 N-benzylidene benzylamine 
• 106-45-6 para-thiocresol 
• 622-29-7 N-Benzylidenemethylamine 
• 106-38-7 para-bromotoluene 
• 68-12-2 N,N-dimethyl-formamide 
• 874-60-2 4-methyl-benzoyl chloride 
• 6833-18-7 4-methyl-N-phenylbenzamide 
• 1485-70-7 N-benzylbenzamide 

Downstream Products

• 303024-56-8 N-(4-nitrobenzyl)-4-methylbenzamide 
• 80311-90-6 N-(Hydroxybenzyl)-4-methylbenzamide 
• 99-94-5 p-Toluic acid 
• 51764-85-3 N-(4'-methylbenzoyl)-4-hydroxybenzylamine 
• 114081-67-3 N-Benzyl-4-methyl-benzimidoyl chloride 
• 6833-18-7 4-methyl-N-phenylbenzamide 
• 1485-70-7 N-benzylbenzamide 
• 404942-59-2 (R)-4-methyl-N-(1-phenylethyl)benzamide 
• 104-85-8 para-methylbenzonitrile 
• 1269762-43-7 C₇₅H₁₃NO 
• 589-18-4 4-Methylbenzyl alcohol 
• 100-46-9 benzylamine 
• 1430730-38-3 4-benzyl-5-(4-methylphenyl)-3-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-1,2,4-triazole 
• 891414-34-9 N,N-dibenzyl-N-(4-methylbenzyl)amine 

Relevant academic research and scientific papers

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.

Buchwald-Hartwig amination of aryl esters and chlorides catalyzed by the dianisole-decorated Pd-NHC complex

A modular and generic method for the Buchwald-Hartwig amination reactions of relatively unreactive aryl esters as acyl electrophiles and aryl chlorides as aryl electrophiles has been developed, leading to the efficient synthesis of amides/amines under air conditions and with low catalyst loadings. The success of this catalytic protocol is mainly attributed to the modification of the Pd-IPr skeleton with sterically hindered and electron-donating anisole groups. This method also features good functional group tolerance and excellent chemoselectivities. In summary, the results presented herein suggest the possibility of developing a versatile and general protocol for diverse electrophiles to undergo the Buchwald-Hartwig amination reactions, avoiding too much consideration of the reaction conditions for the substrate-dependent C-N bond formations.

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.

N -Heterocyclic carbene (NHC) catalyzed amidation of aldehydes with amines via the tandem N -hydroxysuccinimide ester formation

A facile method for the amidation of aldehydes by a cascade approach was developed. This methodology, reported for the first time, uses a N-heterocyclic carbene (NHC) as the catalyst, and N-hydroxysuccinimide (NHS) mediated synthesis of amides utilising TBHP as the oxidant. Various substituted aldehydes reacted smoothly with NHS giving the corresponding active esters in moderate to good yields, which facilely converted into amides in one pot. In addition, the drug moclobemide was synthesized to represent the practical utility of the developed methodology. This journal is

Dehydrogenative amide synthesis from alcohols and amines utilizing N-heterocyclic carbene-based ruthenium complexes as efficient catalysts: The influence of catalyst loadings, ancillary and added ligands

The metal-catalyzed dehydrogenative coupling of alcohols and amines to access amides has been recognized as an atom-economic and environmental-friendly process. Apart from the formation of the amide products, three other kinds of compounds (esters, imines and amines) may also be produced. Therefore, it is of vital importance to investigate product distribution in this transformation. Herein, N-heterocyclic carbene-based Ru (NHC/Ru) complexes [Ru-1]-[Ru-5] with different ancillary ligands were prepared and characterized. Based on these complexes, we selected condition A (without an added NHC precursor) and condition B (with an added NHC precursor) to comprehensively explore the selectivity and yield of the desired amides. After careful evaluation of various parameters, the Ru loadings, added NHC precursors and the electronic/steric properties of ancillary NHC ligands were found to have considerable influence on this catalytic process.

Direct synthesis of amides and imines by dehydrogenative homo or cross-coupling of amines and alcohols catalyzed by Cu-MOF

Oxidative dehydrogenative homo-coupling of amines to imines and cross-coupling of amines with alcohols to amides was achieved with high to moderate yields at room temperature in THF using Cu-MOF as an efficient and recyclable heterogeneous catalyst under mild conditions. Different primary benzyl amines and alcohols could be utilized for the synthesis of a wide variety of amides and imines. The Cu-MOF catalyst could be recycled and reused four times without loss of catalytic activity.

Half-Sandwich Ruthenium Complexes Bearing Hemilabile κ2-(C,S)?Thioether-Functionalized NHC Ligands: Application to Amide Synthesis from Alcohol and Amine

Amide synthesis is one of the most crucial transformations in chemistry and biology. Among various catalytic systems, N-heterocyclic carbene (NHC)-based ruthenium (Ru) catalyst systems have been proven to be active for direct synthesis of amides by sustainable acceptorless dehydrogenative Coupling of primary alcohols with amines. Most often, these catalytic systems usually use monodentate NHC and thus require an additional ligand to obtain high reactivity and selectivity. In this work, a series of cationic Ru(II)(η6-p-cymene) complexes with thioether-functionalized N-heterocyclic carbene ligands (imidazole and benzimidazole-based) have been prepared and fully characterized. These complexes have then been used in the amidation reaction and the most promising one (i. e. 3 c) has been applied on a large range of substrates. High conversions albeit with moderate yields have generally been obtained.

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.

Copper and N-Heterocyclic Carbene-Catalyzed Oxidative Amidation of Aldehydes with Amines

A one-pot two-step oxidative process has been developed for the tert-butyl hydroperoxide mediated transformation of aldehydes and amines into amides catalyzed by copper(I) iodide and an N-heterocyclic carbene. The process is additive-free and does not require the amine to be transformed into its hydrochloride salts. The method is simple and practicable, has a broad substrate scope, and uses economical, feasible, and abundant reagents.

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.