5279-51-6

Basic information

• Product Name: 4'-METHOXY-N-METHYLFORMANILIDE
• Synonyms: 4'-METHOXY-N-METHYLFORMANILIDE;N-(4-METHOXYPHENYL)-N-METHYLFORMAMIDE;4'-Methoxy-N-methylformanilide
• CAS NO: 5279-51-6
• Molecular Formula: C₉H₁₁NO₂
• Molecular Weight: 165.18914
• Mol File: 5279-51-6.mol

Chemical Properties

• Melting Point: 26 °C
• Boiling Point: 309.5°C at 760 mmHg
• Flash Point: 26 °C
• Appearance: /
• Density: 1.11g/cm³
• Vapor Pressure: 0.000635mmHg at 25°C
• Refractive Index: 1.55
• PKA: 1.25±0.50(Predicted)
• CAS DataBase Reference: 4'-METHOXY-N-METHYLFORMANILIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-METHOXY-N-METHYLFORMANILIDE(5279-51-6)
• EPA Substance Registry System: 4'-METHOXY-N-METHYLFORMANILIDE(5279-51-6)

Safety Data

• Hazardous Substances Data: 5279-51-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4'-METHOXY-N-METHYLFORMANILIDE is used as an intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new medications.
Used in Dye Industry:
4'-METHOXY-N-METHYLFORMANILIDE is used as an intermediate in the synthesis of dyes, contributing to the production of a range of colorants.
Used in Organic Chemical Production:
4'-METHOXY-N-METHYLFORMANILIDE is used as a raw material in the production of other organic chemicals, playing a role in the synthesis of various compounds.
Used in Organic Synthesis:
4'-METHOXY-N-METHYLFORMANILIDE is used as a reagent in organic synthesis, aiding in the formation of desired products in chemical reactions.
Used in Antimicrobial Applications:
4'-METHOXY-N-METHYLFORMANILIDE is used as a potential antimicrobial agent due to its antimicrobial and antifungal properties, showing promise in the development of new antimicrobial agents.

InChI:InChI=1/C9H11NO2/c1-10(7-11)8-3-5-9(12-2)6-4-8/h3-7H,1-2H3

Upstream product

• 64-18-6 formic acid 
• 5961-59-1 N-methyl-N-(4-methoxyphenyl)amine 
• 613-90-1 benzoyl cyanide 
• 701-56-4 4-methoxy-N,N-dimethylanilne 
• 108-24-7 acetic anhydride 
• 85462-16-4 N-Methyl-O-p-nitrophenylsulphonylhydroxylamine 
• 123-11-5 4-methoxy-benzaldehyde 
• 3400-21-3 2-methyl-3-anisyloxaziridine 
• 5470-34-8 4-methoxyformanilide 
• 77-78-1 dimethyl sulfate 
• 150760-95-5 formic acid cyanomethyl ester 
• 536-74-3 phenylacetylene 
• 149-73-5 trimethyl orthoformate 
• 123-39-7 N-Methylformamide 

Downstream Products

• 502925-19-1 (E)-1,2-Dichloro-N,N'-bis-(4-methoxy-phenyl)-N,N'-dimethyl-ethene-1,2-diamine 
• 701-56-4 4-methoxy-N,N-dimethylanilne 
• 1643531-70-7 (E)-N-[2-(6-bromopyridine-2-yl)vinyl]-4-methoxy-N-methylaniline 
• 1643531-69-4 (E)-N,N-diethyl-3-[N-(4-methoxyphenyl)-N-(methyl)amino]acrylamide 
• 1643531-68-3 (E)-4-methoxy-N-methyl-N-[(2-phenylsulfinyl)vinyl]aniline 
• 1643531-67-2 (E)-3-[N-(4-methoxyphenyl)-N-(methyl)amino]acrylonitrile 
• 1643531-59-2 (E)-tert-butyl 3-{[N-(4-methoxyphenyl)-N-(methyl)amino]}acrylate 
• 909132-75-8 (E)-β-(4-methoxy-N-methylanilino)acrylic acid ethyl ester 
• 643735-25-5 7-methoxy-4-(4-methoxyphenyl)-1-methylbenzo[f][1,4]-diazepine-2,3-dicarboxylic anhydride 
• 764-93-2 1-decyne 
• 85021-22-3 2-Methoxy-5,8,11-trimethyl-5,6,11,12-tetrahydro-dibenzo[b,f][1,5]diazocine 
• 5961-59-1 N-methyl-N-(4-methoxyphenyl)amine 
• 1421493-01-7 N-(4-methoxyphenyl)-N-methyl-carbamoyl cyanide 

Relevant articles and documents

Additive-free selective methylation of secondary amines with formic acid over a Pd/In2O3 catalyst

Formic acid is used as the sole carbon and hydrogen source in the methylation of aromatic and aliphatic amines to methylamines. The reaction proceeds via a formylation/transfer hydrogenation pathway over a solid Pd/In2O3 catalyst without the need for any additive.

Metalized Carbon Nitrides for Efficient Catalytic Functionalization of CO2

As an effective approach toward sustainability and global carbon balance, the reductive conversion of CO2 into value-added chemicals is of considerable significance. Here, by simply calcining the mixture of NH4SCN and KCl in an air atmosphere, potassium dopants and negatively charged electron-rich centers are simultaneously introduced into carbon nitride materials via a metalation engineering strategy. The resultant metalized catalysts with deprotonated imide sites and doped potassium ions demonstrate much-enhanced activity for catalyzing CO2 reductive hydrosilylation with excellent conversion and >90% selectivity, whereas the pristine carbon nitride catalyst shows only negligible activity. Both experimental and theoretical results reveal the crucial role of the negatively charged electron-rich centers and potassium dopants in tailoring the energy band positions and electronic structure for the efficient donor-acceptor interaction and much increased driving force for CO2 reduction. The present work offers molecular-level insights into the boosted CO2 reduction activity via engineering the electronic structure of the metalized carbon nitride catalyst and reducing the energy offset between frontier molecular orbitals of CO2 and the catalyst, which can provide a conceptual guide for further development of efficient catalytic CO2 reduction systems.

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.

Study on the mild, rapid and selective difluorocarbene-mediated triclassification of iododifluoroacetophenone with secondary amines and tree model for product classification

Difluorocarbene is a very active and widely used intermediate in organic synthesis. In this work, a room temperature difluorocarbene-mediated triclassification reaction of iododifluoroacetophenone (2) and secondary amines with mild condition, short reaction time (only 10 min) and high selectivity had been studied, which produced one of the following three substances: N-CF2H derivatives (up to 87% yield), formamides (82–89% yield) or the recycled starting secondary amines. This phenomenon was related to the structural stability of the corresponding products. If unstable, it would be hydrolyzed to formamides first, and then further hydrolyzed to starting amines. Based on the geometric structure of the raw materials, the corresponding prediction tree model was established, which provided guidance for the further application of difluoromethylation of Vemurafenib (1ee) and AZD9291 (1ff).

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.

Preparation method of formamide compound

The invention belongs to CO. 2 The invention relates to the technical field of activation conversion and related chemistry, and provides a preparation method of a formamide compound, which uses carbon dioxide. The amide compound and phenylsilane are used as raw materials, and the formamide compound is synthesized under the action of the nano porous palladium catalyst. The invention mainly provides a novel simple catalytic system and utilizes CO. 2 C1 The catalytic system has the advantages of mild reaction conditions, simple experiment operation, good functional group compatibility and the like. Because carbon dioxide is abundant, cheap and easily available and renewable C1 , The invention has great application value and social economic benefits.

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.

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.

Immobilized Zn(OAc)2on bipyridine-based periodic mesoporous organosilica for N -formylation of amines with CO2and hydrosilanes

Zinc acetate (Zn(OAc)2) was successfully immobilized on a bipyridine-based periodic mesoporous organosilica (BPy-PMO-TMS), as confirmed by solid-state NMR and energy-dispersive X-ray spectroscopies, X-ray diffractometry, and nitrogen adsorption/desorption isotherm analyses. The immobilized Zn complex, Zn(OAc)2(BPy-PMO-TMS), exhibited good catalytic activity during the N-formylations of amines and amides with CO2 and PhSiH3 to produce the corresponding formamides. Zn(OAc)2(BPy-PMO-TMS) with a lower Zn loading was found to exhibit higher catalytic activity.

Ionization of Porous Hypercrosslinked Polymers for Catalyzing Room-Temperature CO2 Reduction via Formamides Synthesis

Porous materials with heterogeneous nature occupy a pivotal position in the chemical industry. This work described a facile pre- and post-synthetic approach to modify porous hypercrosslinked polymer with quaternary ammonium bromide, rendering it as efficient catalyst for CO2 conversion. The as-prepared porous ionic polymer (PiP@QA) displayed an improved specific surface area of 301 m2·g?1 with hierarchically porous structure, good selective adsorption of CO2, as well as high ion density. Accordingly, PiP@QA catalyst exhibited excellent catalytic performances for the solvent-free synthesis of various formamides from CO2, amines and phenylsilane under 35?°C and 0.5?MPa. We speculated that the superior catalytic efficiency and broad substrate scope of this catalyst could be resulted from the synergistic effect of flexible ionic sites with unique nanoporous channel that might increase the collision probability of reactants and active sites as well as enhance the diffusion of reactants and products during the reaction process. With the good reusability, PiP@QA was also available for the efficient conversion of simulated flue gas (15% CO2 in N2, v/v) into target formamides with quantitative selectivity at room temperature, which further highlighted its industrial application potential in chemical recycling the real-word CO2 to valuable products. Graphic Abstract: [Figure not available: see fulltext.].