582-78-5

Basic information

• Product Name: 4'-methylbenzanilide
• Synonyms: N-(4-methylphenyl)benzamide;N-(p-Methylphenyl)benzamide;N-(p-Tolyl)benzamide;p-Benzotoluide;p-Benzotoluidide
• CAS NO: 582-78-5
• Molecular Formula: C₁₄H₁₃NO
• Molecular Weight: 211.26
• EINECS: 209-491-8
• Mol File: 582-78-5.mol
• Article Data: 306

Chemical Properties

• Melting Point: 158°C
• Boiling Point: 350.95°C (rough estimate)
• Flash Point: 154.9 °C
• Appearance: /
• Density: 1.2020
• Refractive Index: 1.5780 (estimate)
• PKA: 13.52±0.70(Predicted)
• CAS DataBase Reference: 4'-methylbenzanilide(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-methylbenzanilide(582-78-5)
• EPA Substance Registry System: 4'-methylbenzanilide(582-78-5)

Safety Data

• Hazardous Substances Data: 582-78-5(Hazardous Substances Data)

Usage

Description

4'-methylbenzanilide, also known as N-(4-methylphenyl)benzamide, is an organic compound derived from the amidation of aryl halides and N-arylation of heterocycles with aryl halides using cyclohexanediamine ligands. It is characterized by its unique chemical structure and reactivity, which makes it a versatile compound for various applications in different industries.

Uses

Used in Pharmaceutical Industry:
4'-methylbenzanilide is used as a reactant for the preparation of 2-arylbenzoxazoles, which are important intermediates in the synthesis of various pharmaceutical compounds. The application reason is its ability to undergo copper-catalyzed regioselective intramolecular oxidative C-O coupling of benzanilides, leading to the formation of biologically active molecules with potential therapeutic properties.
Used in Chemical Synthesis:
In the field of chemical synthesis, 4'-methylbenzanilide is used as a key building block for the creation of complex organic molecules. Its unique reactivity and structural features make it a valuable component in the synthesis of various organic compounds, including those with potential applications in materials science, agrochemicals, and other specialty chemicals.
Used in Research and Development:
4'-methylbenzanilide is also utilized in research and development settings, where it serves as a model compound for studying the reactivity and properties of similar amides and benzanilides. This helps researchers gain a deeper understanding of the underlying chemical mechanisms and develop new strategies for the synthesis of novel compounds with improved properties and applications.

Upstream product

• 134-84-9 4-Methylbenzophenone 
• 2998-92-7 (Z)-phenyl(p-tolyl)methanone oxime 
• 93-58-3 benzoic acid methyl ester 
• 106-49-0 p-toluidine 
• 93-99-2 benzoic acid phenyl ester 
• 98-88-4 benzoyl chloride 
• 93-97-0 benzoic acid anhydride 
• 65-85-0 benzoic acid 
• 621-01-2 N,N'-Bis(p-tolyl)thiourea 
• 5405-15-2 N-benzyl-N-(4-methylphenyl)amine 
• 67-56-1 methanol 
• 100-52-7 benzaldehyde 
• 106-47-8 4-chloro-aniline 
• 78486-48-3 β-(N-benzoyl-p-toluidino)-acrolein 

Downstream Products

• 17646-67-2 benzoic acid-(N-chloro-p-toluidide) 
• 77791-07-2 N-(2-bromo-4-methylphenyl)-benzamide 
• 151965-63-8 4--4-methyl-2,5-cyclohexadienone N-benzoylimine 
• 69825-52-1 (Benzoyl-p-tolyl-amino)-acetic acid ethyl ester 
• 582-80-9 p-benzamidobenzoic acid 
• 100-52-7 benzaldehyde 
• 501-60-0 1,2-di(p-tolyl)diazene 
• 81743-88-6 2-(4-methylphenyl)-1,2-benzisoselenazol-3(2H)-one 
• 15926-80-4 4.6-Bis--isophthalsaeure-dimethylester 
• 14016-00-3 6-methyl-2-phenylbenzoxazole 
• 10205-58-0 6-methyl-2-phenyl-1,3-benzothiazole 
• 60566-08-7 N,N'-bis(4-methylphenyl)-N-benzoylbenzamidine 
• 1253778-96-9 N-(4-((N-(phenylsulfonyl)phenylsulfonamido)methyl)phenyl)benzamide 
• 1360571-17-0 4-tert-butylphenyl N-(4-methylphenyl)benzimidate 

Relevant articles and documents

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.

Chromium-catalyzed ligand-free amidation of esters with anilines

Amides are important structural motifs in pharmaceutical and agrochemical chemistry because of the intriguing biological active properties. We report here the amidation of commercially available esters with anilines that was promoted by low-cost and air-stable chromium(III) pre-catalyst combined with magnesium, providing access to amides. This reaction occurs without the use of external ligands in a simple operation. Mechanistic studies indicate that a reactive aminated Cr species responsible for the amidation can be considered, which may be formed by reaction of low-valent Cr with aniline followed by reduction with hydrogen evolution.

Fe-mediated synthesis of: N -aryl amides from nitroarenes and acyl chlorides

Amides are prevalent in nature and valuable functional compounds in agrochemical, pharmaceutical, and materials industries. In this work, we developed a selective and mild method for the synthesis of N-aryl amides. Starting from commercially available nitroarenes and acyl halides, N-aryl amides with good yields can be obtained in water. Especially in the process of transformation, Fe dust is the only reductant and additive, and the reaction can be easily performed on a large scale.