1929-89-1

Usage

Uses

Used in Agriculture:
N-Phenyl-2-furancarboxamide is used as an insecticide for protecting crops from insect infestations, ensuring a healthy and productive yield.
Used in Vector-Borne Disease Control:
N-Phenyl-2-furancarboxamide is studied for its potential use in controlling vector-borne diseases such as malaria and dengue fever, contributing to public health and disease prevention efforts.
It is important to handle N-Phenyl-2-furancarboxamide with care, as it can be toxic to humans and the environment if not used properly.

InChI:InChI=1/C11H9NO2/c13-11(10-7-4-8-14-10)12-9-5-2-1-3-6-9/h1-8H,(H,12,13)

Upstream product

• 527-69-5 2-furancarbonyl chloride 
• 62-53-3 aniline 
• 611-13-2 2-furoic acid methyl ester 
• 17357-38-9 S-phenyl furan-2-carbothioate 
• 98-01-1 furfural 
• 112-92-5 1-octadecanol 
• 555-16-8 4-nitrobenzaldehdye 
• 67-63-0 isopropyl alcohol 
• 51583-40-5 2-(trimethylstannyl)furan 
• 103-71-9 phenyl isocyanate 
• 20842-02-8 potassium furan-2-carboxylate 
• 128100-67-4 1,2-bis(1,1-dioxido-3-oxobenzo[d]isothiazol-2(3H)-yl)ethane-1,2-dione 
• 2979-48-8 1-(2-furoyl)-imidazole 
• 1026046-13-8 2-furanoyl sulfonate 

Downstream Products

• 10243-03-5 furan-2-carbothioic acid anilide 
• 58472-54-1 5-bromo-furan-2-carboxylic acid-(4-bromo-anilide) 
• 1569-98-8 2-(furan-2-yl)-1,3-benzothiazole 
• 34653-56-0 5-(1,3-benzothiazol-2-yl)furan-2-carbaldehyde 
• 74442-13-0 C₄H₃OC(O)N(SCCl₂CFCl₂)C₆H₅ 
• 74442-14-1 C₄H₃OC(O)N(SCClFCFCl₂)C₆H₅ 
• 6436-22-2 N-phenyl-furan-2-carboximidoyl chloride 
• 1214752-44-9 N-(furan-2-yl(phenylimino)methyl)-N-phenylfuran-2-carboxamide 
• 1404192-00-2 4,5,6-triphenylfuro[2,3-c]pyridin-7(6H)-one 
• 1237829-82-1 2-(furan-2-yl)-4-phenylquinazoline 
• 18249-70-2 1-benzyl-2-(furan-2-yl)-1H-benzo[d]imidazole 
• 6436-38-0 N-benzyl-N'-phenylfuran-2-carboximidamide 
• 98-00-0 (2-furyl)methyl alcohol 
• 62-53-3 aniline 

Relevant academic research and scientific papers

Pd(OAc)2/AgOAc catalytic system based bidentate ligand directed regiocontrolled C-H arylation and alkylation of the C-3 position of thiophene- and furan-2-carboxamides

A contemporary method is reported for the Pd(OAc)2/AgOAc catalytic system based bidentate ligand directed, regioselective C-H activation and C-C bond formation at the C-3 position of thiophene- and furan-2-carboxamides, which are derived from 8

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.

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.

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.

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 metal-free picolinamide assisted electrochemical ortho-trifluoromethylation of arylamines

An eco-friendly and effective electrochemical process was developed for the ortho-trifluoromethylation of arylamines using CF3SO2Na as the trifluoromethyl source, affording the desired products in moderate to good yields with high regioselectivity under mild reaction conditions. Importantly, the requirement for both transition metals and oxidants utilized in previous methods were avoided. A radical mechanism was proposed on the basis of various control experiments.

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.

Simple Synthesis of Amides via Their Acid Chlorides in Aqueous TPGS-750-M

The technology of surfactant chemistry is employed for amide bond construction via the reaction of acyl chlorides with amines in 2 wt % TPGS-750-M aqueous solution. Specifically, this highly efficient method enables a chromatography-free scalable process and recycling of the TPGS-750-M solution.

Synthesis of amides from acid chlorides and amines in the bio-based solvent Cyrene

Cyrene as a bio-alternative dipolar aprotic solvent: a waste minimizing and molar efficient protocol for the synthesis of amides from acid chlorides and primary amines in the bio-available solvent Cyrene is disclosed. This protocol removed the use of toxic solvents, such as dimethylformamide and dichloromethane. A simple aqueous work-up procedure for the removal of the high boiling solvent Cyrene resulted in up to a 55-fold increase in molar efficiency (Mol E.%) versus standard operating procedures. In order to rapidly compare the molar efficiency of this process against other methodologies an Excel based Mol. E% calculator was developed that automates many of the calculations. An investigation into the hydration of Cyrene found that it readily hydrates to form a geminal diol in the presence of water and that this process is exothermic.

Iodine-mediated aryl transfer reaction from arylhydrazine hydrochlorides to nitriles

An iodine-promoted, metal-, base-, and solvent-free cross-coupling reaction was developed for the synthesis of various useful secondary amides via an aryl N-addition reaction of aryl groups to cyano groups. This aryl transfer reaction proceeds with arylhydrazine hydrochlorides serving as the aryl donors. A labelling experiment shows that the N atom in the product comes from the cyano group of the nitriles, which are low in cost. A plausible radical-driven mechanism is also proposed.