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

Uses

N-(4-methylphenyl)benzamide is prepared through copper-catalyzed amidation of aryl halides and N-arylation of heterocycles with aryl halides using cyclohexanediamine ligands. It is used as a reactant in preparation of 2-arylbenzoxazoles by copper-catalyzed regioselective intramolecular oxidative C-O coupling of benzanilides.

Upstream product

• 93-58-3 benzoic acid methyl ester 
• 106-49-0 p-toluidine 
• 93-99-2 benzoic acid phenyl ester 
• 65-85-0 benzoic acid 
• 621-01-2 N,N'-Bis(p-tolyl)thiourea 
• 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 
• 78486-48-3 β-(N-benzoyl-p-toluidino)-acrolein 
• 83728-58-9 N-(4-Pyrrolidin-1-yl-pyridine-2-carbonyl)-N-p-tolyl-benzamide 
• 1003-03-8 Cyclopentamine 
• 83728-57-8 N-(4-Morpholin-4-yl-pyridine-2-carbonyl)-N-p-tolyl-benzamide 
• 622-57-1 N-ethyl-p-tolylamine 

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 
• 77791-06-1 N-(2-chloro-4-methylphenyl)benzamide 
• 111273-17-7 4-(4-methylphenyl)-3-phenyl-1,2,4-oxadiazol-5(4H)-one 
• 36954-50-4 N-(4-methylphenyl)-benzamide oxime 
• 15926-80-4 4.6-Bis--isophthalsaeure-dimethylester 
• 14016-00-3 6-methyl-2-phenylbenzoxazole 
• 1256360-91-4 C₂₂H₁₈ClNO 
• 1256360-77-6 C₁₉H₁₉NO₂ 
• 1256360-75-4 C₂₁H₂₃NO₃ 
• 871570-97-7 butyl (N-p-methylphenyl-isoindolin-1-on-3-yl)acetate 
• 1256360-74-3 C₂₄H₂₁NO₃ 
• 1256360-76-5 C₁₇H₁₄N₂O 

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.

Self-Assembled 2,3-Dicyanopyrazino Phenanthrene Aggregates as a Visible-Light Photocatalyst

In this study, 2,3-dicyanopyrazino phenanthrene (DCPP), a commodity chemical that can be prepared at an industrial scale, was used as a photocatalyst in lieu of Ru or Ir complexes in C-X (X = C, N, and O) bond-forming reactions under visible-light irradiation. In these reactions, [DCPP]n aggregates were formed in situ through physical π-πstacking of DCPP monomers in organic solvents. These aggregates exhibited excellent photo- and electrochemical properties, including a visible light response (430 nm), long excited-state lifetime (19.3 μs), high excited-state reduction potential (Ered([DCPP]n*/[DCPP]n·-) = +2.10 V vs SCE), and good reduction stability. The applications of [DCPP]n aggregates as a versatile visible-light photocatalyst were demonstrated in decarboxylative C-C cross-coupling, amidation, and esterification reactions.

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.