6833-23-4

Basic information

• Product Name: 3-METHOXY-N-PHENYLBENZAMIDE
• Synonyms: 3-METHOXY-N-PHENYLBENZAMIDE;3-Methoxybenzanilide;M-Anisanilide;N-Phenyl-3-MethoxybenzaMide;N-Phenyl-M-anisaMide
• CAS NO: 6833-23-4
• Molecular Formula: C₁₄H₁₃NO₂
• Molecular Weight: 227.26
• Product Categories: Aromatics Compounds;Aromatics
• Mol File: 6833-23-4.mol

Chemical Properties

• Melting Point: 114-116°C
• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Methanol
• CAS DataBase Reference: 3-METHOXY-N-PHENYLBENZAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHOXY-N-PHENYLBENZAMIDE(6833-23-4)
• EPA Substance Registry System: 3-METHOXY-N-PHENYLBENZAMIDE(6833-23-4)

Safety Data

• Hazardous Substances Data: 6833-23-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3-Methoxy-N-phenylbenzamide is used as a synthetic intermediate for the production of various organic compounds. Its unique chemical structure allows it to be a versatile building block in the synthesis of a wide range of molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Methoxy-N-phenylbenzamide is used as a key component in the development of new drugs. Its incorporation into drug molecules can potentially enhance their therapeutic properties, such as improving their efficacy, selectivity, or bioavailability.
Used in Agrochemical Industry:
3-Methoxy-N-phenylbenzamide also finds application in the agrochemical industry, where it is utilized in the synthesis of novel pesticides, herbicides, and other crop protection agents. Its integration into these compounds can lead to the development of more effective and environmentally friendly products.
Used in Dye and Pigment Industry:
The light pink solid nature of 3-Methoxy-N-phenylbenzamide makes it a potential candidate for use in the dye and pigment industry. It can be employed in the creation of new colorants for various applications, such as textiles, plastics, and printing inks.
Used in Research and Development:
3-Methoxy-N-phenylbenzamide is also used in research and development settings, where it can serve as a model compound for studying various chemical reactions and mechanisms. Its unique properties make it an interesting subject for exploration in academic and industrial research labs.

Upstream product

• 694-59-7 pyridine N-oxide 
• 87281-97-8 3-Methoxy-N-phenyl-benzimidoyl chloride 
• 113399-36-3 4-Dimethylamino-1-{(3-methoxy-phenyl)-[(Z)-phenylimino]-methyl}-pyridinium; chloride 
• 10365-98-7 3-methoxyphenylboronic acid 
• 103-71-9 phenyl isocyanate 
• 591-50-4 iodobenzene 
• 5813-86-5 m-methoxybenzamide 
• 100-09-4 4-methoxybenzoic acid 
• 579-75-9 2-Methoxybenzoic acid 
• 201230-82-2 carbon monoxide 
• 35692-26-3 3-trimethoxyphenyltrimethoxysilane 
• 62-53-3 aniline 
• 10259-22-0 ethyl 3-methoxybenzoate 
• 98-95-3 nitrobenzene 

Downstream Products

• 154822-34-1 3-hydroxy-4-methoxy-2-phenyl-3-(4-pyridyl)-2,3-dihydro-1H-isoindolin-1-one 
• 918536-57-9 2-[2-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-1-(2-methoxyphenyl)-ethyl]-3-methoxy-benzoic acid 
• 1457958-23-4 N,N'-diphenyl-3-methoxybenzamidine 
• 27559-45-1 3-hydroxy-N-phenyl-benzamide 
• 27834-99-7 ethyl (3-methoxybenzoyl)acetate 
• 5892-84-2 (3-Methoxy-benzoyl)-phenyl-carbamic acid isopropyl ester 
• 81308-21-6 N-(3-methoxybenzyl)aniline 
• 62-53-3 aniline 
• 1207356-64-6 C₂₀H₂₇NO₂Si 
• 748164-82-1 C₂₂H₂₁NO₄ 

Relevant articles and documents

Cobalt-Catalyzed Deoxygenative Hydroboration of Nitro Compounds and Applications to One-Pot Synthesis of Aldimines and Amides

The commercially available and bench-stable Co(acac)2 ligated with bis[(2-diphenylphosphino)phenyl] ether (dpephos) was employed for selective room temperature hydroboration of nitro compounds with HBPin (TOF up to 4615 h?1), tolerating halide, hydroxy, amino, ether, ester, lactone, amide and heteroaromatic functionalities. These reactions offered a direct access to a variety of N-borylamines RN(H)BPin, which were in situ treated with aldehydes and carboxylic acids to produce a series of aldimines and secondary carboxamides without the need for dehydrating and/or coupling reagents. Combination of these transformations in a sequential one-pot manner allowed for direct and selective synthesis of aldimines and secondary carboxamides from readily available and inexpensive nitro compounds.

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.

Cu-catalyzed arylation of bromo-difluoro-acetamides by aryl boronic acids, aryl trialkoxysilanes and dimethyl-aryl-sulfonium salts: New entries to aromatic amides

We describe a mechanism-guided discovery of a synthetic methodology that enables the preparation of aromatic amides from 2-bromo-2, 2-difluoroacetamides utilizing a copper-catalyzed direct arylation. Readily available and structurally simple aryl precursors such as aryl boronic acids, aryl trialkoxysilanes and dimethyl-aryl-sulfonium salts were used as the source for the aryl substituents. The scope of the reactions was tested, and the reactions were insensitive to the electronic nature of the aryl groups, as both electron-rich and electron-deficient aryls were successfully introduced. A wide range of 2-bromo-2, 2-difluoroacetamides as either aliphatic or aromatic secondary or tertiary amides were also reactive under the developed conditions. The described synthetic protocols displayed excellent efficiency and were successfully utilized for the expeditious preparation of diverse aromatic amides in good-to-excellent yields. The reactions were scaled up to gram quantities.

Practical one-pot amidation of N -Alloc-, N -Boc-, and N -Cbz protected amines under mild conditions

A facile one-pot synthesis of amides from N-Alloc-, N-Boc-, and N-Cbz-protected amines has been described. The reactions involve the use of isocyanate intermediates, which are generated in situ in the presence of 2-chloropyridine and trifluoromethanesulfonyl anhydride, to react with Grignard reagents to produce the corresponding amides. Using this reaction protocol, a variety of N-Alloc-, N-Boc-, and N-Cbz-protected aliphatic amines and aryl amines were efficiently converted to amides with high yields. This method is highly effective for the synthesis of amides and offers a promising approach for facile amidation.

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.

Copper-catalyzed Goldberg-type C-N coupling in deep eutectic solvents (DESs) and water under aerobic conditions

An efficient and selectiveN-functionalization of amides is first reportedviaa CuI-catalyzed Goldberg-type C-N coupling reaction between aryl iodides and primary/secondary amides run either in Deep Eutectic Solvents (DESs) or water as sustainable reaction media, under mild and bench-type reaction conditions (absence of protecting atmosphere). Higher activities were observed in an aqueous medium, though the employment of DESs expanded and improved the scope of the reaction to include also aliphatic amides. Additional valuable features of the reported protocol include: (i) the possibility to scale up the reaction without any erosion of the yield/reaction time; (ii) the recyclability of both the catalyst and the eutectic solvent up to 4 consecutive runs; and (iii) the feasibility of the proposed catalytic system for the synthesis of biologically active molecules.

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.

Copper-catalyzed aerobic oxidative C-C bond cleavage of simple ketones for the synthesis of amides

A Cu-catalyzed oxidative amidation of simple ketones with amines via carbon-carbon (C-C) bond cleavage has been developed. A number of aryl and alkyl ketones could be easily converted to amides using cheap copper salt as the catalyst and O2 as the oxidant with a wide range of amines, including primary and secondary amines. This method shows a notable advantage of the broad scope for the substrate, thus providing a practical approach to amides. A plausible mechanism is proposed based on the preliminary experiments.

Clickable coupling of carboxylic acids and amines at room temperature mediated by SO2F2: A significant breakthrough for the construction of amides and peptide linkages

The construction of amide bonds and peptide linkages is one of the most fundamental transformations in all life processes and organic synthesis. The synthesis of structurally ubiquitous amide motifs is essential in the assembly of numerous important molecules such as peptides, proteins, alkaloids, pharmaceutical agents, polymers, ligands and agrochemicals. A method of SO2F2-mediated direct clickable coupling of carboxylic acids with amines was developed for the synthesis of a broad scope of amides in a simple, mild, highly efficient, robust and practical manner (>110 examples, >90% yields in most cases). The direct click reactions of acids and amines on a gram scale are also demonstrated using an extremely easy work-up and purification process of washing with 1 M aqueous HCl to provide the desired amides in greater than 99% purity and excellent yields.