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

• 613-90-1 benzoyl cyanide 
• 623-10-9 N-(4-methylphenyl)hydroxylamine 
• 19064-77-8 C-phenyl-N-p-tolyl-nitrone 
• 15999-95-8 N-(4-methylphenyl)benzimidoyl chloride 
• 75-77-4 chloro-trimethyl-silane 
• 135308-30-4 N-(Cyclohex-1-enecarbonyloxy)-N-p-tolyl-benzamide 
• 201230-82-2 carbon monoxide 
• 99-99-0 1-methyl-4-nitrobenzene 
• 591-50-4 iodobenzene 
• 106-49-0 p-toluidine 
• 884-09-3 phenyl thiobenzoate 
• 10371-42-3 S-(4-methylphenyl) thiobenzoate 
• 4906-35-8 S-(4-chlorophenyl) benzothioate 
• 1219-32-5 S-4-nitrophenyl thiobenzoate 

Downstream Products

• 17646-67-2 benzoic acid-(N-chloro-p-toluidide) 
• 77791-07-2 N-(2-bromo-4-methylphenyl)-benzamide 
• 5373-55-7 N-(4-methylphenyl)thiobenzamide 
• 6393-42-6 4-methyl-2,6-dinitroaniline 
• 77791-06-1 N-(2-chloro-4-methylphenyl)benzamide 
• 75092-47-6 6-methyl-2,4-diphenyl-3-p-tolyl-3,4-dihydro-quinazolin-4-ol 
• 860566-26-3 3-nitro-benzoic acid-(4-methyl-2,6-dinitro-anilide) 
• 582-80-9 p-benzamidobenzoic acid 
• 15999-95-8 4-methylphenylbenzimidoyl chloride 
• 26242-93-3 N-(4-methyl-2-nitrophenyl) benzamide 
• 89-62-3 4-methyl-2-nitroaniline 
• 151965-63-8 4--4-methyl-2,5-cyclohexadienone N-benzoylimine 
• 121003-21-2 N-methoxyacetyl-N-(p-tolyl)benzamide 
• 100-52-7 benzaldehyde 

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.

Iron-catalyzed cross-coupling of N?methoxy amides and arylboronic acids for the synthesis of N-aryl amides

An efficient iron-catalyzed synthesis of N-aryl amides from N?methoxy amides and arylboronic acids is developed. FeCl3 is used as the sole catalyst for the cross-coupling reaction between N?methoxy amides and arylboronic acids without any other

Direct Amidation of Esters by Ball Milling**

The direct mechanochemical amidation of esters by ball milling is described. The operationally simple procedure requires an ester, an amine, and substoichiometric KOtBu and was used to prepare a large and diverse library of 78 amide structures with modest to excellent efficiency. Heteroaromatic and heterocyclic components are specifically shown to be amenable to this mechanochemical protocol. This direct synthesis platform has been applied to the synthesis of active pharmaceutical ingredients (APIs) and agrochemicals as well as the gram-scale synthesis of an active pharmaceutical, all in the absence of a reaction solvent.