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 
• 82947-19-1 1-(N-tosyl-p-methylphenylamino)-3-(p-methylphenylimino)-1-propene 

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.

Supported CuII Single-Ion Catalyst for Total Carbon Utilization of C2 and C3 Biomass-Based Platform Molecules in the N-Formylation of Amines

The shift from fossil carbon sources to renewable ones is vital for developing sustainable chemical processes to produce valuable chemicals. In this work, value-added formamides were synthesized in good yields by the reaction of amines with C2 and C3 biomass-based platform molecules such as glycolic acid, 1,3-dihydroxyacetone and glyceraldehyde. These feedstocks were selectively converted by catalysts based on Cu-containing zeolite 5A through the in situ formation of carbonyl-containing intermediates. To the best of our knowledge, this is the first example in which all the carbon atoms in biomass-based feedstocks could be amidated to produce formamide. Combined catalyst characterization results revealed preferably single CuII sites on the surface of Cu/5A, some of which form small clusters, but without direct linking via oxygen bridges. By combining the results of electron paramagnetic resonance (EPR) spin-trapping, operando attenuated total reflection (ATR) IR spectroscopy and control experiments, it was found that the formation of formamides might involve a HCOOH-like intermediate and .NHPh radicals, in which the selective formation of .OOH radicals might play a key role.

Reductive Formylation of Nitroarenes using HCOOH over Bimetallic C?N Framework Derived from the Integration of MOF and COF

CoZn embedded C?N framework is prepared by the carbonization of CoZn containing MOF integrated with COF porous architecture in Ar atmosphere. The graphitic nature of porous carbon is confirmed from Raman analysis. The porosity and nanostructure information are retrieved from N2-sorption and transmission electron microscopic analysis, respectively. The incorporation of different metals and their oxidation states and types of nitrogen present in the C?N framework are confirmed from X-ray photoelectron spectroscopy. The basicity of the materials is determined from a CO2-temperature programmed desorption. ZnCo embedded C?N framework exhibits excellent activity in the selective reductive formylation using HCOOH. For comparison, more than 15 materials are prepared, and their activities are compared. Several control experiments are performed to establish a structure-activity relation. The recycling experiment, hot-filtration test, and poisoning experiment demonstrate the metal embedded porous C?N framework‘s recyclability and stability. A reaction mechanism for the reductive N-formylation of nitroaromatics is presented based on structure-activity relationship, control reactions, and physicochemical characterizations. The development of interesting MOF-COF-derived metal nanoclusters embedded C?N framework for selective reductive formylation of nitroaromatics using formic acid will be highly attractive to catalysis researchers and industrialists.