328-20-1

Usage

Uses

Used in Chemical Synthesis:
2-Fluorodiphenylamine is used as a key intermediate in the production of dyes, which are essential for coloring textiles, plastics, and other materials. Its unique chemical structure contributes to the color properties of these dyes.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 2-fluorodiphenylamine serves as an intermediate for the synthesis of various medicinal compounds, potentially contributing to the development of new drugs and therapies.
Used in Plastics and Rubber Manufacturing:
2-Fluorodiphenylamine is utilized as a stabilizer in the manufacturing of plastics and rubbers to enhance their durability and resistance to degradation, thereby extending the lifespan of these materials.

InChI:InChI=1/C12H10FN/c13-11-8-4-5-9-12(11)14-10-6-2-1-3-7-10/h1-9,14H

Upstream product

• 108-86-1 bromobenzene 
• 399-31-5 N-(2-fluorophenyl)acetamide 
• 1072-85-1 o-fluorobromobenzene 
• 103-84-4 Acetanilid 
• 71-43-2 benzene 
• 348-54-9 2-Fluoroaniline 
• 108-90-7 chlorobenzene 
• 1993-03-9 o-fluorophenylboronic acid 
• 586-96-9 Nitrosobenzene 
• 98-80-6 phenylboronic acid 
• 591-50-4 iodobenzene 
• 348-52-7 1-Fluoro-2-iodobenzene 
• 62-53-3 aniline 
• 32090-98-5 N-phenyl-2-fluoroacetanilide 

Downstream Products

• 129574-36-3 N-(2-fluorophenyl)-4-hydroxy-3-methyl-2(1H)-quinolone 
• 951117-47-8 [PN]H 
• 1638490-78-4 1-(2-fluorophenyl)-4-phenylquinolin-2(1H)-one 
• 3665-72-3 5,10-diphenyl-5,10-dihydrophenazine 
• 129574-30-7 4-Chloro-1-(2-fluoro-phenyl)-3-methyl-1H-quinolin-2-one 
• 129574-30-7 4-Chloro-1-(2-fluoro-phenyl)-3-methyl-1H-quinolin-2-one 
• 129574-30-7 N-(2-fluorophenyl)-4-chloro-3-methyl-2(1H)-quinolone 
• 391-26-4 1-fluoro-9H-carbazole 
• 386-16-3 N-phenyl-N-2-fluorophenylbenzamide 

Relevant academic research and scientific papers

Copper-catalyzed, ceric ammonium nitrate mediated N-arylation of amines

Cu-Catalyzed, ligand- and base-free cross-coupling of aryl boronic acids with primary and secondary amines has been reported. This ‘Chan-Evans-Lam' reaction has revealed that at room temperature, with a catalytic amount of copper(ii) acetate and ceric ammonium nitrate (CAN) as an oxidant, N-arylation can result in an effective C-N bond formation. This air stable, practical, robust protocol enables tolerance towards a variety of functional groups on both boronic acid and amine partners.

Diamines as interparticle linkers for silica-titania supported PdCu bimetallic nanoparticles in Chan-Lam and Suzuki cross-coupling reactions

A series of highly efficient amine functionalized SiO2-TiO2 supported bimetallic PdCu catalysts with varied metal composition have been synthesized. Ethane-1,2-diamine, butane-1,4-diamine and hexane-1,6-diamine were employed as interparticle linkers for amine functionalization of a SiO2-TiO2 support material so as to study the effect of pendant chain length on stabilization and immobilization of bimetallic nanoparticles. The shortest carbon chain length on the support provided the best results, which may be due to the trapping of metal nanoparticles more efficiently by the basic nitrogen sites. The catalytic activities of these materials were evaluated for C-N and C-C coupling reactions. The most active catalyst, Pd1Cu1@12DA-STS, was characterized by various techniques including SEM, HR-TEM, ICP-AES, XRD, FTIR, EDX, CHN analysis and TGA studies. Moreover, the synthesized catalyst was found to be recyclable for up to five runs without significant loss of activity.

Ligand-Free Iron-Catalyzed C-F Amination of Diarylamines: A One-Pot Regioselective Synthesis of Diaryl Dihydrophenazines

A one-pot synthesis of various 5,10-diaryl-5,10-dihydrophenazines (DADHPs) from diarylamines has been achieved by using an iron-catalyzed C-F amination. Homodimerization of magnesium diarylamides, followed by defluorinative intramolecular cyclization (dou

Ligand-Free Iron-Catalyzed C-F Amination of Diarylamines: A One-Pot Regioselective Synthesis of Diaryl Dihydrophenazines

A one-pot synthesis of various 5,10-diaryl-5,10-dihydrophenazines (DADHPs) from diarylamines has been achieved by using an iron-catalyzed C-F amination. Homodimerization of magnesium diarylamides, followed by defluorinative intramolecular cyclization (dou

Copper immobilized at a covalent organic framework: An efficient and recyclable heterogeneous catalyst for the Chan-Lam coupling reaction of aryl boronic acids and amines

A polyimide covalent organic framework (PI-COF) with high thermal and chemical stabilities has been readily prepared from commercially available and inexpensive reagents and was employed as an effective support for heterogeneous copper. It was demonstrated that the obtained Cu@PI-COF is a highly active heterogeneous catalyst which can effectively promote the Chan-Lam coupling reaction of aryl boronic acids and amines in an open flask without the aid of any base or additive. In addition, the catalyst could be readily recovered from the reaction mixture by simple filtration and reused for at least eight cycles without any observable change in structure and catalytic activity.

Synthesis of Di(hetero)arylamines from Nitrosoarenes and Boronic Acids: A General, Mild, and Transition-Metal-Free Coupling

The synthesis of di(hetero)arylamines by a transition-metal-free cross-coupling between nitrosoarenes and boronic acids is reported. The procedure is experimentally simple, fast, mild, and scalable and has a wide functional group tolerance, including carbonyls, nitro, halogens, free OH and NH groups. It also permits the synthesis of sterically hindered compounds.

Sulfonato-diketimine Copper(II) Complexes: Synthesis and Application as Catalysts in Chan-Evans-Lam Couplings

Copper complexes bearing a diketimino-sulfonate ligand, LCu(NO3)(NCMe), were prepared and proved to be stable to water for several hours in solution. Prolonged standing in the presence of water or strong bases led to desulfonation of the ligand. LCu(NO3) was inactive in the polymerization of lactide (in the presence of benzyl alcohol), but showed high activity for the Chan-Evans-Lam coupling of a variety of amines and anilines. Couplings do not require addition of base, ligand, or molecular sieves. Mechanistic investigations indicate a catalytic cycle involving dioxygen as the required oxidant, precoordination of boronic acid to the sulfonate group, and transmetalation occurring prior to reaction with the nucleophile.

Highly Chemoselective Iridium Photoredox and Nickel Catalysis for the Cross-Coupling of Primary Aryl Amines with Aryl Halides

A visible-light-promoted iridium photoredox and nickel dual-catalyzed cross-coupling procedure for the formation C?N bonds has been developed. With this method, various aryl amines were chemoselectively cross-coupled with electronically and sterically diverse aryl iodides and bromides to forge the corresponding C?N bonds, which are of high interest to the pharmaceutical industries. Aryl iodides were found to be a more efficient electrophilic coupling partner. The coupling reactions were carried out at room temperature without the rigorous exclusion of molecular oxygen, thus making this newly developed Ir-photoredox/Ni dual-catalyzed procedure very mild and operationally simple.

Solvent-free N-arylation of amines with arylboronic acids under ball milling conditions

Solvent-free coupling reactions of arylboronic acids with various amines were presented under ball milling conditions, achieving the aromatic amine coupling products with yields ranging from moderate to good. This type of mechano-chemistry exhibited advantages of solvent-free property, high efficiency, simple work-up procedure and eco-friendliness. This journal is the Partner Organisations 2014.

Ligand-free C-N bond formation in aqueous medium using a reusable Cu-Mn bimetallic catalyst

A general ligand-free protocol has been described for the recyclable and reusable Cu-Mn catalyzed C-N bond forming cross coupling reaction of arylboronic acids with various amines to form N-arylated amine products in aqueous medium affording excellent yields under ambient conditions, in 3-4 h.