23099-05-0

Basic information

• Product Name: 3-METHYLBENZANILIDE
• Synonyms: AKOS 244-41;3-METHYLBENZANILIDE;3-TOLUANILIDE;M-METHYLBENZANILIDE;M-TOLUANILIDE;3-Methyl-N-phenylbenzaMide, 97%;3-Methylbenzanilide(WX619011)
• CAS NO: 23099-05-0
• Molecular Formula: C₁₄H₁₃NO
• Molecular Weight: 211.26
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
• Mol File: 23099-05-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-METHYLBENZANILIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYLBENZANILIDE(23099-05-0)
• EPA Substance Registry System: 3-METHYLBENZANILIDE(23099-05-0)

Safety Data

• Hazardous Substances Data: 23099-05-0(Hazardous Substances Data)

Upstream product

• 2998-93-8 3-methyl-benzophenone-seqcis-oxime 
• 109596-37-4 2-amino-3-methyl-benzoic acid-(N-methyl-anilide); hydrochloride 
• 62-53-3 aniline 
• 1711-06-4 3-Methylbenzoyl chloride 
• 620-23-5 m-tolyl aldehyde 
• 109257-45-6 2-(2-propinyl)-4-pentinoic acid anilide 
• 694-59-7 pyridine N-oxide 
• 87281-94-5 3-methyl-N-phenyl-benzimidoyl chloride 
• 937-01-9 trimethyl(3-methylphenyl)stannane 
• 103-71-9 phenyl isocyanate 
• 101476-38-4 4-Dimethylamino-1-{[(Z)-phenylimino]-m-tolyl-methyl}-pyridinium; chloride 
• 105417-02-5 4-methyl-N′-(phenyl(m-tolyl)methylene)benzenesulfonohydrazide 
• 425366-13-8 phenyl-m-tolylmethylidyne-ammonium 
• 425365-96-4 3-methyl-N-phenyl-benzimidic acid 4-cyano-phenyl ester 

Downstream Products

• 87281-94-5 3-methyl-N-phenyl-benzimidoyl chloride 
• 134312-84-8 5-Methyl-2-methylselanyl-N-phenyl-benzamide 
• 87281-94-5 3-methyl-N-phenyl-benzimidoyl chloride 
• 134312-89-3 5-Methyl-2-phenyl-benzo[d]isoselenazol-3-one 
• 306325-32-6 C₂₁H₁₇NO₂ 
• 210967-20-7 (4-aminophenyl)(3-methylphenyl)methanone 
• 1207356-67-9 C₂₀H₂₇NOSi 
• 1253388-61-2 C₂₂H₂₅NO 
• 1253388-60-1 C₂₈H₂₁NO 
• 73230-98-5 3-methyl-N- (4-nitrophenyl)benzamide 
• 587-03-1 3-methylbenzyl alcohol 
• 62-53-3 aniline 
• 1211-32-1 2-(m-tolyl)benzo[d]thiazole 
• 3335-31-7 3-methyl-N-phenylbenzothioamide 

Relevant articles and documents

Anilinolysis of picryl benzoate derivatives in methanol: Reactivity, regioselectivity, kinetics, and mechanism

The reaction of picryl benzoate derivatives 1a-g with aniline in methanol proceeds through CO-O and Ar-O bond cleavage pathways. Furthermore, the reactivity of these esters toward anilinolysis is correlated to the energy gap between highest occupied molecular orbital aniline and lowest unoccupied molecular orbital of each ester. The regioselectivity of acyl-oxygen versus aryl-oxygen cleavage is also discussed. The overall rate constants k tot split into kCO-O (the rate constant of acyl-oxygen cleavage) and kAr-O (rate constant of aryl-oxygen cleavage). The CO-O bond cleavage advances through a stepwise mechanism in which the formation of the tetrahedral intermediate is the rate-determining step. The Ar-O bond cleavage continues through a SNAr mechanism in which the departure of the leaving group from the Meisenheimer complex occurs rapidly after its formation in the rate-determining step.

Nickel-Catalyzed Reductive Cross-Coupling of N-Acyl and N-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides

Herein we report a Ni-catalyzed reductive transamidation of conveniently available N-acyl benzotriazoles with alkyl, alkenyl, and aryl nitro compounds, which afforded various amides with good yields and a broad substrate scope. The same catalytic reaction conditions were also applicable for N-sulfonyl benzotriazoles, which could undergo smooth reductive coupling with nitroarenes and nitroalkanes to afford the corresponding sulfonamides.

Visible-Light Carbon Nitride-Catalyzed Aerobic Cyclization of Thiobenzanilides under Ambient Air Conditions

A metal-free heterogeneous photocatalysis has been developed for the synthesis of benzothiazoles via intramolecular C-H functionalization/C-S bond formation of thiobenzanilides by inexpensive graphitic carbon nitride (g-C3N4) under visible-light irradiation. This reaction provides access to a broad range of 2-substituted benzothiazoles in high yields under an air atmosphere at room temperature without addition of a strong base or organic oxidizing reagents. In addition, the catalyst was found to be stable and reusable after five reaction cycles.

Visible-Light-Promoted Iron-Catalyzed N-Arylation of Dioxazolones with Arylboronic Acids

A visible-light-promoted and simple iron salt-catalyzed N-arylation was achieved efficiently under external photosensitizer-free conditions. Arylboronic acids and bench-stable dioxazolones were used for this cross-coupling reaction. This reaction features high reactivity, wide substrate scope, good functional group tolerance, simple operation procedure, and mild reaction conditions. Preliminary mechanistic investigations were conducted to support a radical pathway. This method may contribute to shift the paradigm of iron-catalyzed C-N bond construction and nitrene transfer chemistry.

Metal-free transamidation of benzoylpyrrolidin-2-one and amines under aqueous conditions

N-Acyl lactam amides, such as benzoylpyrrolidin-2-one, benzoylpiperidin-2-one, and benzoylazepan-2-one reacted with amines in the presence of DTBP and TBAI to afford the transamidated products in good yields. The reactions were conducted under aqueous conditions and good functional group tolerance was achieved. Both aliphatic and aromatic primary amines displayed good activity under metal-free conditions. A radical reaction pathway is proposed.

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.

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.

A practical and sustainable protocol for direct amidation of unactivated esters under transition-metal-free and solvent-free conditions

In this paper, a NaOtBu-mediated synthesis approach was developed for direct amidation of unactivated esters with amines under transition-metal-free and solvent-free conditions, affording a series of amides in good to excellent yields at room temperature. In particular, an environmentally friendly and practical workup procedure, which circumvents the use of organic solvents and chromatography in most cases, was disclosed. Moreover, the gram-scale production of representative products3a,3wand3auwas efficiently realized by applying operationally simple, sustainable and practical procedures. Furthermore, this approach was also applicable to the synthesis of valuable molecules such as moclobemide (a powerful antidepressant), benodanil and fenfuram (two commercial agricultural fungicides). These results demonstrate that this protocol has the potential to streamline amide synthesis in industry. Meanwhile, quantitative green metrics of all the target products were evaluated, implying that the present protocol is advantageous over the reported ones in terms of environmental friendliness and sustainability. Finally, additional experiments and computational calculations were carried out to elucidate the mechanistic insight of this transformation, and one plausible mechanism was provided on the basis of these results and the related literature reports.

N-Phenylbenzamide derivatives as alternative oxidase inhibitors: Synthesis, molecular properties, 1H-STD NMR, and QSAR

In the present work, 117 N-phenylbenzamides (NPDs) were prepared and evaluated against recombinant AOX from the fungal pathogen Moniliophthora perniciosa. 1H, 13C NMR, FTIR, and mass spectra provided structural information on NPDs. The library compounds were tested as Alternative Oxidase inhibitors in two different assays using the model yeast Pichia pastoris: cell growth and oxygen consumption assays. The most active compound, 3FH, was further characterized by DRX and 1H-NMR-STD. Single crystal X-ray diffraction showed intra- and intermolecular interactions of 3FH in solid-state and elucidated its 3D structural configuration. 1H-NMR-STD allowed us to derive protein-ligand interactions in a membrane-mimetic system and evidenced an outstanding interaction of 3FH with this enzyme. Results of both biological assays were used as input to Quantitative Structure-Activity Relationship models, which highlighted the more important molecular fragments contributions for protein-ligand interaction.

Nickel/briphos-catalyzed transamidation of unactivated tertiary amides

The transamidation of tertiary amides was achieved via nickel catalysis in combination with briphos ligands. N-Methyl-N-phenylbenzamide derivatives reacted with primary amines in the presence of NiCl2/briphos L4 to provide the transamidated products in moderate to good yields. Primary aromatic amines delivered higher product yields than aliphatic amines.