459-25-6

Usage

Uses

Used in Pharmaceutical Industry:
1-Fluoro-4-formamidobenzene is used as a synthetic intermediate for the development of new pharmaceutical compounds. Its unique structure allows for the creation of novel molecules with potential medicinal properties, contributing to the advancement of drug discovery and therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 1-Fluoro-4-formamidobenzene serves as a key component in the synthesis of various agrochemical products. Its incorporation into these compounds can enhance their effectiveness in agricultural applications, such as pest control and crop protection.
Used in Research Applications:
1-Fluoro-4-formamidobenzene is utilized in various research settings, particularly for studying the properties and reactions of organic compounds. Its unique structure provides a valuable platform for understanding the behavior of fluorinated and formamide-containing molecules, furthering scientific knowledge in the field of organic chemistry.

InChI:InChI=1/C7H6FNO/c8-6-1-3-7(4-2-6)9-5-10/h1-5H,(H,9,10)

Upstream product

• 123-91-1 1,4-dioxane 
• 371-40-4 4-fluoroaniline 
• 403-46-3 4-fluoro-N,N-dimethylaniline 
• 459-59-6 4-fluoro-N-methylaniline 
• 64-18-6 formic acid 
• 3296-02-4 p-azidofluorobenzene 
• 79-14-1 glycolic Acid 
• 2146-07-8 p-fluoroaniline hydrochloride 
• 77287-34-4 formamide 
• 51673-84-8 dimethoxyacetaldehyde 
• 124-38-9 carbon dioxide 
• 350-46-9 4-Fluoronitrobenzene 
• 456-22-4 4-Fluorobenzoic acid 
• 16664-09-8 4-fluorobenzoyl azide 

Downstream Products

• 74701-95-4 C₆H₄FN(CHO)SCFCl₂ 
• 79175-46-5 N-(4-chlorophenylmercuri)-4'-fluoroformanilide 
• 79175-47-6 N-(4-methylphenylmercuri)-4'-fluoroformanilide 
• 79175-43-2 N-(3,4,5-trichlorophenylmercuri)-4-fluoroformanilide 
• 114067-93-5 ethyl 1-(4-fluorophenyl)-1H-imidazole-4-carboxylate 
• 1474042-00-6 4-fluorophenyl(1-selena-3-azaspiro[5.5]undec-2-en-2-yl)amine hydrobromide 
• 1474041-91-2 1-(2-cyclohex-1-enylethyl)-3-(4-fluorophenyl)selenourea 
• 1444155-44-5 N-(4-pyridyl)-N-(4-fluorophenyl)formamide 

Relevant academic research and scientific papers

Access to Unsymmetrically Substituted Diaryl Gold N-Acyclic Carbene (NAC) and N-Heterocyclic Carbene (NHC) Complexes via the Isonitrile Route

A variety of unsymmetric diaryl gold N-acyclic carbene (NAC) complexes was synthesized via the isonitrile route by three different methods: (a) solvent free in a melt, (b) mechanochemically and (c) in THF at room temperature. The latter method can also be used to synthesize unsaturated gold NHC complexes. These methods overall offer access to a broad array of new complexes and remove one of the previous limitations of the isonitrile route to NAC and NHC complexes of gold, namely the inability to react with the less nucleophilic aromatic amines. The new complexes also proved to be successful as pre-catalysts in the gold-catalyzed phenol synthesis. (Figure presented.).

Design, synthesis and anticancer evaluation of 3-methyl-1H-indazole derivatives as novel selective bromodomain-containing protein 4 inhibitors

Bromodomain-containing Protein 4 (BRD4), an ‘epigenetic reader’, regulates chromatin structure and gene expression via recognizing and binding acetylated lysine in histones. BRD4 has become a therapeutic target for cancers because it promotes the expression of the tumor genes, such as c-Myc, NF-κB, and Bcl-2. In this study, a new series of 3-methyl-1H-indazole derivatives were designed via virtual screening and structure-based optimization. All compounds were synthesized and evaluated for their inhibitory activities to BRD4-BD1 and their antiproliferative effects in cancer cell lines. Among them, several compounds (such as 9d, 9u and 9w) exhibited strong BRD4-BD1 affinities and inhibition activities, and potently suppressed MV4;11 cancer cell line proliferation. Among them, compound 9d showed excellent selectivity for BRD4 and effectively suppressed c-Myc, the downstream protein of BRD4. This study provided new lead compounds for further biological evaluation on BRD4.

Novel 4-phenoxypyridine derivatives bearing imidazole-4-carboxamide and 1,2,4-triazole-3-carboxamide moieties: Design, synthesis and biological evaluation as potent antitumor agents

Two series of novel 4-phenoxypyridine derivatives containing imidazole-4-carboxamide and 4-methyl-5-oxo-4,5-dihydro-1,2,4-triazole-3-carboxamide moieties were synthesized and evaluated for their in vitro inhibitory activities against c-Met kinase and anti

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.

Preparation and catalytic evaluation of a palladium catalyst deposited over modified clinoptilolite (Pd&at;MCP) for chemoselective N-formylation and N-acylation of amines

Novel palladium nanoparticles stabilized by clinoptilolite as a natural inexpensive zeolite prepared and used for N-formylation and N-acylation of amines at room temperature at environmentally benign reaction conditions in good to excellent yields. Pd (II) was immobilized on the surface of clinoptilolite via facile multi-step amine functionalization to obtain a sustainable, recoverable, and highly active nano-catalyst. The structural and morphological characterizations of the catalyst carried out using XRD, FT-IR, BET and TEM techniques. Moreover, the catalyst is easily recovered using simple filtration and reused for 7 consecutive runs without any loss in activity.

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.

Selective N-formylation of amines catalysed by Ag NPs festooned over amine functionalized SBA-15 utilizing CO2 as C1 source

N-formylation of amines using CO2 as C1 source has been an uphill transformation in the catalysis research as it involves the utilization of abundant thermodyanamically stable and kinetically inert CO2 to form the N-formylated products, which are potential intermediates for the synthesis of valuable chemicals. Previously various noble as well as non-noble metal nanoparticles have been employed for N-formylation of amines. However, herein for the first time we explored N-formylation reaction under lenient conditions utilizing silver nanoparticles, which are decorated over amine functionalized periodically ordered 2D-hexagonal SBA-15 material, serving as a robust heterogeneous catalyst. The AgNPs@SBA-15-NH2 has been intensively characterized by powder XRD, Brunauer-Emmett-Teller (BET), FEG-TEM, SEM, XPS, TGA, CO2-TPD, FTIR and UV–vis spectroscopic analyses. This supported AgNPs material showed remarkable catalytic activity for N-formylation over a wide range of amines under 0.5 MPa CO2 pressure and at mild temperature (35 °C) conditions. In addition, this AgNPs@SBA-15-NH2 material exhibited high chemical stability and reusability, suggesting its promising future in the CO2 fixation reactions.

HCl-mediated transamidation of unactivated formamides using aromatic amines in aqueous media

We report transamidation protocol to synthesize a range of secondary and tertiary amides from weakly nucleophilic aromatic and hetero-aryl amines with low reactive formamide derivatives, utilizing hydrochloric acid as catalyst. This current acid mediated strategy is beneficial because it eliminates the need for a metal catalyst, promoter or additives in the reaction, simplifies isolation and purification. Notably, this approach conventionally used to synthesize molecules on gram scales with excellent yields and a high tolerance for functional groups.

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.