3085-54-9

Usage

Uses

Used in Pharmaceutical Industry:
4-Methylformanilide is used as a key intermediate in the synthesis of various pharmaceuticals, contributing to the development of new medications and therapeutic agents. Its chemical properties allow it to be a versatile building block in the creation of diverse drug molecules.
Used in Dye Industry:
In the dye industry, 4-Methylformanilide is utilized as an intermediate for the production of different types of dyes. Its ability to form a variety of chemical bonds makes it suitable for creating a range of colorants used in textiles, plastics, and other materials.
Used in Organic Synthesis:
4-Methylformanilide is used as a solvent in organic synthesis, facilitating various chemical reactions that are essential for the production of complex organic compounds. Its solubility in organic solvents makes it a valuable component in many chemical processes.
Used in Chemical Industry as a Reagent:
As a reagent in the chemical industry, 4-Methylformanilide is employed to catalyze or participate in a multitude of chemical reactions. Its reactivity and stability in certain conditions make it a useful tool for achieving desired outcomes in chemical processes.

InChI:InChI=1/C8H9NO/c1-7-2-4-8(5-3-7)9-6-10/h2-6H,1H3,(H,9,10)

Upstream product

• 64-18-6 formic acid 
• 106-49-0 p-toluidine 
• 77287-34-4 formamide 
• 64-19-7 acetic acid 
• 109-99-9 tetrahydrofuran 
• 2101-86-2 p-methylazidobenzene 
• 201230-82-2 carbon monoxide 
• 99-99-0 1-methyl-4-nitrobenzene 
• 622-52-6 p-methylphenylthiourea 
• 5469-72-7 1-deoxy-1-p-toluidino-D-fructose 
• 7175-47-5 4-methylphenyl isocyanide 
• 18197-22-3 N-formylformamide 
• 32978-00-0 Isopropenyl formate 
• 111333-97-2 formic acid pentafluorophenyl ester 

Downstream Products

• 16596-03-5 N,N'-di-p-tolylformamidine 
• 80535-18-8 4-(4-methylphenyl)-4H-1,2,4-triazole 
• 105971-45-7 N-(4-methylphenyl)-2-methyltetrahydropyrrole 
• 10527-16-9 10-chloro-9-anthraldehyde 
• 22071-69-8 formic acid-(N-nitroso-p-toluidide) 
• 621-00-1 1,3-di-p-tolylurea 
• 26060-31-1 N-(4-methylphenyl)thioformamide 
• 877-43-0 2,6-dimethylquinoline 
• 93663-20-8 formic acid-(N-bromo-p-toluidide) 
• 7175-47-5 4-methylphenyl isocyanide 
• 104-85-8 para-methylbenzonitrile 
• 89-62-3 4-methyl-2-nitroaniline 
• 622-57-1 N-ethyl-p-tolylamine 
• 104175-33-9 2,6-dimethylquinoline-4-carboxylic acid 

Relevant academic research and scientific papers

Metal-Free, Rapid, and Highly Chemoselective Reduction of Aromatic Nitro Compounds at Room Temperature

In this study, we developed a metal-free and highly chemoselective method for the reduction of aromatic nitro compounds. This reduction was performed using tetrahydroxydiboron [B2(OH)4] as the reductant and 4,4′-bipyridine as the organocatalyst and could be completed within 5 min at room temperature. Under optimal conditions, nitroarenes with sensitive functional groups, such as vinyl, ethynyl, carbonyl, and halogen, were converted into the corresponding anilines with excellent selectivity while avoiding the undesirable reduction of the sensitive functional groups.

Copper-Catalyzed Cascade N-Dealkylation/N-Methyl Oxidation of Aromatic Amines by Using TEMPO and Oxygen as Oxidants

A novel tandem N-dealkylation and N-methyl aerobic oxidation of tertiary aromatic amines to N-arylformamides using copper and TEMPO has been developed. This methodology suggested an alternative synthetic route from N-methylarylamines to N-arylformamides.

Catalyst freeN-formylation of aromatic and aliphatic amines exploiting reductive formylation of CO2using NaBH4

Herein, we report a sustainable approach forN-formylation of aromatic as well as aliphatic amines using sodium borohydride and carbon dioxide gas. The developed approach is catalyst free, and does not need pressure or a specialized reaction assembly. The reductive formylation of CO2with sodium borohydride generates formoxy borohydride speciesin situ, as confirmed by1H and11B NMR spectroscopy. Thein situformation of formoxy borohydride species is prominent in formamide based solvents and is critical for the success of theN-formylation reactions. The formoxy borohydride is also found to promote transamidation reactions as a competitive pathway along with reductive functionalization of CO2with amine leading toN-formylation of amines.

Borane-Trimethylamine Complex as a Reducing Agent for Selective Methylation and Formylation of Amines with CO2

We report herein that a borane-trimethylamine complex worked as an efficient reducing agent for the selective methylation and formylation of amines with 1 atm CO2 under metal-free conditions. 6-Amino-2-picoline serves as a highly efficient catalyst for the methylation of various secondary amines, whereas in its absence, the formylation of primary and secondary amines was achieved in high yield with high chemoselectivity. Mechanistic studies suggest that the 6-amino-2-picoline-borane catalytic system operates like an intramolecular frustrated Lewis pair to activate CO2.

Recyclable Oxofluorovanadate-Catalyzed Formylation of Amines by Reductive Functionalization of CO2 with Hydrosilanes

An efficient method has been developed for the reductive amination of CO2 by using readily available and recyclable oxofluorovanadates as catalysts. Various amines are transformed into the desired N-formylated products in moderate to excellent yields at room temperature in the presence of phenylsilane. Mechanistic studies based on in situ infrared spectroscopy suggest a reaction pathway initiated through F?Si interactions. The activated phenylsilane allows for CO2 insertion to produce phenylsilyl formate, which undergoes attack by the amine to generate the target product.

Method for preparing formamide compound by using MCOF to catalyze CO2 as carbon source at normal temperature and pressure

The invention provides a method for preparing a formamide compound by using MCOF to catalyze CO2 as a carbon source at normal temperature and pressure, and belongs to the technical field of chemistry and chemical engineering. Under the conditions of normal temperature and normal pressure, CO2 is used as a carbon source to realize N-formylation reaction of various amine substrates. The method has the advantages that the reaction system uses the metal ion-doped two-dimensional covalent organic framework MCOF as the catalyst, CO2 is reduced at normal temperature and normal pressure to provide acyl, high-pressure hydrogen and toxic CO are prevented from being used, and the reaction conditions are mild (normal temperature and normal pressure). According to the method for preparing the formamide, the greenhouse gas carbon dioxide serves as a carbon source, the cost is low, operation is easy, reaction conditions are mild (normal temperature and normal pressure), the yield of the prepared formamide product is excellent (99%), and a green synthesis method is provided for N-acylation reaction.

Olefin functionalized IPr.HCl monomer as well as preparation method and application thereof

The invention relates to an olefin functionalized IPr.HCl monomer, a preparation method thereof, a method for preparing an N-heterocyclic carbene functionalized organic polymer (PS-IPr-x) by using the olefin functionalized IPr.HCl monomer, and application of the N-heterocyclic carbene functionalized organic polymer as a heterogeneous catalyst for catalyzing reduction N-formylation of carbon dioxide and amine. A heterogeneous catalyst is prepared by using cheap and easily available DVB as a polymerization cross-linking agent through an AIBN-initiated olefin polymerization method, and has the advantages of low preparation cost and simple preparation method. Meanwhile, the catalytic activity of the catalyst is obviously higher than that of reported catalysts, and the catalyst has a wide practical application prospect.

Functionalizing HY zeolite with sulfonic acid, a micro-meso structure reusable catalyst for organic transformations

A new class of sulfonic acid functionalized HY zeolite (HY-N-SA) catalyst has been prepared and characterized by some method such as XRD, FT-IR, FESEM, TEM, TGA, NH3-TPD and N2 physisorption. The result shows the micro-meso structure for catalyst without ordering in the mesophase. Then, the HY-N-SA micro-meso structure was used as an acidic catalyst to synthesize of coumarins via Pechmann reaction and facile transformation of amines to formamides under solvent-free condition. To consider the effect of acidity and kind and size of porous on the catalyst activity, this catalyst was compared with NaY-N-SA and MCM-N-SA and pure porous material (NaY and MCM-41). The significant advantages of HY-N-SA with respect to other catalysts are short reaction times, high yields, pure products, mild conditions and easy work-up. In addition, we report an original and environmentally friendly solvent-free procedure which reusability of catalyst makes this method nearly green and environmentally friendly.

Facile N-Formylation of Amines on Magnetic Fe3O4?CuO Nanocomposites

A facile, eco-friendly, efficient, and recyclable heterogeneous catalyst is synthesized by immobilizing copper impregnated on mesoporous magnetic nanoparticles. The surface chemistry analysis of Fe3O4?CuO nanocomposites (NCs) by XRD and XPS demonstrates the synergistic effect between Fe3O4 and CuO nanoparticles, providing mass-transfer channels for the catalytic reaction. TEM images clearly indicate the impregnation of CuO onto mesoporous Fe3O4. This hydrothermally synthesized eco-friendly and highly efficient Fe3O4?CuO NCs are applied as a magnetically retrievable heterogeneous catalyst for the N-formylation of wide range of aliphatic, aromatic, polyaromatic and heteroaromatic amines using formic acid as a formylating agent at room temperature. The catalytic activity of the NCs for N-formylation is attributable to the synergistic effect between Fe3O4 and CuO nanoparticles. The N-formylated product is further employed for the synthesis of biologically active quinolone moieties.