1747-80-4

Usage

Uses

Used in Organic Synthesis:
2-Fluorobenzanilide is used as a building block in organic synthesis for the preparation of various pharmaceutical and agrochemical products. Its unique chemical properties, including the presence of a fluorine atom, make it a valuable component in the creation of new and improved compounds.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 2-fluorobenzanilide is utilized as a key intermediate for the development of new drugs. Its potential biological activities and ability to be modified and incorporated into complex molecular structures make it a promising candidate for drug discovery and development.
Used in Drug Discovery and Development:
2-Fluorobenzanilide has been studied for its applications in drug discovery and development due to its potential biological activities. Researchers are interested in exploring its properties and how it can be used to create new therapeutic agents that address various medical conditions.

InChI:InChI=1/C13H10FNO/c14-12-9-5-4-8-11(12)13(16)15-10-6-2-1-3-7-10/h1-9H,(H,15,16)

Upstream product

• 62-53-3 aniline 
• 393-52-2 2-Fluorobenzoyl chloride 
• 591-50-4 iodobenzene 
• 89-99-6 2-fluorobenzylamine 
• 66003-76-7 Diphenyliodonium triflate 
• 445-28-3 2-fluorobenzamide 
• 24652-66-2 2-fluorobenzaldehyde oxime 
• 98-80-6 phenylboronic acid 
• 445-29-4 o-fluoro-benzoic acid 
• 326902-16-3 2-fluoro-N-(2-iodophenyl)benzamide 
• 349612-20-0 2-bromo-N-(2-fluorophenyl)benzanilide 
• 1629-11-4 2-fluoro-N-(2-chlorophenyl)benzamide 
• 394-35-4 methyl 2-fluorobenzoate 
• 443-26-5 2-fluoro-benzoic acid ethyl ester 

Downstream Products

• 5892-76-2 (2-Fluoro-benzoyl)-phenyl-carbamic acid isopropyl ester 
• 575451-90-0 2-fluoro-4'-pyrrolidinobenzophenone 
• 2027-54-5 2-fluoro-N-phenyl-thiobenzamide 
• 64922-13-0 N-(Dichloro-fluoro-methylsulfanyl)-2-fluoro-N-phenyl-benzamide 
• 5472-23-1 10-phenylacridin-9(10H)-one 
• 1201835-75-7 1-methoxy-10-phenylacridin-9(10H)-one 
• 1073486-93-7 2,3-diphenyl-4-carboxylic acid ethyl ester-isoquinolin-1(2H)-one 
• 1747-46-2 2-(2-fluorophenyl)-1,3-benzothiazole 
• 14959-72-9 2,3,4-triphenylisoquinolin-1(2H)-one 
• 1438253-93-0 C₁₃H₉ClFN 
• 941547-81-5 1-benzyl-2-(2-fluorophenyl)-1H-benzo[d]imidazole 
• 1609460-21-0 2-(2-fluorophenyl)-4-phenyl-quinazoline 
• 1609460-28-7 N-benzyl-2-fluoro-N'-phenylbenzimidamide 
• 905139-71-1 2-fluoro-N,N-diphenylbenzamide 

Relevant academic research and scientific papers

Copper-catalyzed Goldberg-type C-N coupling in deep eutectic solvents (DESs) and water under aerobic conditions

An efficient and selectiveN-functionalization of amides is first reportedviaa CuI-catalyzed Goldberg-type C-N coupling reaction between aryl iodides and primary/secondary amides run either in Deep Eutectic Solvents (DESs) or water as sustainable reaction media, under mild and bench-type reaction conditions (absence of protecting atmosphere). Higher activities were observed in an aqueous medium, though the employment of DESs expanded and improved the scope of the reaction to include also aliphatic amides. Additional valuable features of the reported protocol include: (i) the possibility to scale up the reaction without any erosion of the yield/reaction time; (ii) the recyclability of both the catalyst and the eutectic solvent up to 4 consecutive runs; and (iii) the feasibility of the proposed catalytic system for the synthesis of biologically active molecules.

Visible-Light Carbon Nitride-Catalyzed Aerobic Cyclization of Thiobenzanilides under Ambient Air Conditions

A metal-free heterogeneous photocatalysis has been developed for the synthesis of benzothiazoles via intramolecular C-H functionalization/C-S bond formation of thiobenzanilides by inexpensive graphitic carbon nitride (g-C3N4) under visible-light irradiation. This reaction provides access to a broad range of 2-substituted benzothiazoles in high yields under an air atmosphere at room temperature without addition of a strong base or organic oxidizing reagents. In addition, the catalyst was found to be stable and reusable after five reaction cycles.

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.

Metal-free transamidation of benzoylpyrrolidin-2-one and amines under aqueous conditions

N-Acyl lactam amides, such as benzoylpyrrolidin-2-one, benzoylpiperidin-2-one, and benzoylazepan-2-one reacted with amines in the presence of DTBP and TBAI to afford the transamidated products in good yields. The reactions were conducted under aqueous conditions and good functional group tolerance was achieved. Both aliphatic and aromatic primary amines displayed good activity under metal-free conditions. A radical reaction pathway is proposed.

Exploration of Cu-catalyzed regioselective hydrodehalogenation of o-haloanilides using EtOH as hydrogen source

In present work, we have explored a Cu(acac)2/vasicine-catalyzed regioselective hydrodehalogenation methodology of o-haloanilides using EtOH as hydrogen source and solvent. The catalytic system could selectively dehalogenate 2-Br and 2-I, and features regioselective, efficient and functional group tolerance.

Nickel-Catalyzed C-F/N-H Annulation of Aromatic Amides with Alkynes: Activation of C-F Bonds under Mild Reaction Conditions

The Ni-catalyzed reaction of ortho-fluoro-substituted aromatic amides with alkynes results in C-F/N-H annulation to give 1(2H)-isoquinolinones. A key to the success of the reaction is the use of KOtBu or even weak base, such as Cs2CO3. The reaction proceeds in the absence of a ligand and under mild reaction conditions (40-60 °C). DFT calculations suggest that the pathway for this Ni-catalyzed C-F/N-H annulation involves N-H deprotonation, oxidative addition of a C-F bond, migratory insertion of an alkyne, and reductive elimination to form 1(2H)-isoquinolinone derivatives.

Efficient Pd-Catalyzed Hydrodehalogenation of o -Haloanilides in Water

In the present work, we have developed a practical methodology for the hydrodehalogenation of o -haloanilides using PdCl 2at 100 °C under mild conditions in water. The catalytic system could selectively dehalogenate both aryl chloride and aryl bromide and exhibit a broad functional group tolerance.

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.

Exogenous Photosensitizer-, Metal-, and Base-Free Visible-Light-Promoted C-H Thiolation via Reverse Hydrogen Atom Transfer

Visible-light-driven, intramolecular C(sp2)-H thiolation has been achieved without addition of a photosensitizer, metal catalyst, or base. This reaction induces the cyclization of thiobenzanilides to benzothiazoles. The substrate absorbs visible light, and its excited state undergoes a reverse hydrogen-atom transfer (RHAT) with 2,2,6,6-tetramethylpiperidine N-oxyl to form a sulfur radical. The addition of the sulfur radical to the benzene ring gives an aryl radical, which then rearomatizes to benzothiazole via RHAT.

Method for synthesizing amide compound through photocatalysis in water phase

The invention discloses a method for synthesizing an amide compound through photocatalysis in a water phase. The method comprises the following steps: putting catalysis amounts of a free radical initiator, an amine derivative, a carboxylic acid derivative, a phase transfer catalyst, an inorganic base and water into a reaction container, carrying out a reaction in a photocatalysis reaction instrument at certain power under a room temperature condition, after a certain time, carrying out extraction by using a small amount of ethyl acetate, and carrying out recrystallization, so as to obtain theamide compound, wherein the free radical initiator is eosin, methyl orange, sodium persulfate, ammonium persulfate or potassium peroxodisulfate, the phase transfer catalyst is tetrabutylammonium bromide, and the power of the photocatalytic reaction instrument is 5W. By adopting the method disclosed by the invention, toxic thionyl chloride or phosphorus oxychloride is not needed for a chlorinationreaction, water is adopted as a solvent, a novel photocatalysis method is used, and the amide compound with a high yield can be prepared through a room-temperature reaction for 2-5 hours with an incandescent light bulb of 5W, and in addition, the method is simple in aftertreatment, and low in cost and is an ideal green synthesis method of amide compounds.