366-63-2

Usage

Uses

Used in Pharmaceutical Industry:
4-Fluorobenzanilide is utilized as an intermediate in the synthesis of pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its unique structure allows for the creation of a wide range of organic compounds with potential medicinal properties.
Used in Organic Synthesis:
In the field of organic synthesis, 4-Fluorobenzanilide serves as a key building block for the assembly of more complex molecules. Its reactivity and structural features make it a valuable component in the synthesis of various organic compounds.
Used in Medicinal Chemistry:
4-Fluorobenzanilide has been studied for its potential applications in medicinal chemistry, where it may contribute to the discovery of new drugs and therapeutic agents. Its unique structure and properties make it a promising candidate for further research and development.
Used in Pharmacological Research:
4-Fluorobenzanilide has been investigated for its potential pharmacological properties, including its role as a potential analgesic or anti-inflammatory agent. This research aims to explore the compound's therapeutic potential and its ability to alleviate pain or reduce inflammation in various conditions.

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

Upstream product

• 658-13-9 p-fluorobenzoyl cyanide 
• 62-53-3 aniline 
• 824-75-9 p-fluorobenzamide 
• 603-33-8 triphenylbismuthane 
• 456-22-4 4-Fluorobenzoic acid 
• 362-99-2 (4-fluorophenyl)phenylmethanone oxime 
• 403-43-0 4-fluorobenzoyl chloride 
• 201230-82-2 carbon monoxide 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 459-57-4 4-fluorobenzaldehyde 
• 108-86-1 bromobenzene 
• 591-50-4 iodobenzene 
• 362-99-2 (4-fluorophenyl)-phenylmethanone oxime 
• 701-73-5 methyl N-phenyldithiocarbamate 

Downstream Products

• 871123-22-7 (C₆H₅NHCOC₆H₄)2CCH₃C₆H₄NH₂(OC₆H₄)2 
• 397-54-6 2-(4-fluorophenyl)benzoxazole 
• 79606-49-8 N,N-diphenyl-p-fluorobenzamide 
• 1449384-25-1 N-cyclopropyl-4-fluoro-N-phenylbenzamide 
• 459-56-3 4-fluorobenzylic alcohol 
• 62-53-3 aniline 
• 347-88-6 4-fluoro-N-(4-nitrophenyl)benzamide 
• 345-83-5 4-fluorobenzophenone 
• 3800-06-4 2-amino-4'-fluorobenzophenone 
• 10055-40-0 (4-aminophenyl)(4-fluorophenyl)methanone 
• 838-55-1 N-(2-chlorophenyl)-4-fluorobenzamide 
• 33489-70-2 4-fluoro-N-(4-methoxyphenyl)benzamide 

Relevant academic research and scientific papers

Design, Synthesis, and Pharmacological Activity of a New Matrix Metalloproteinase-9 Inhibitor

The new MMP-9 inhibitor 1-{4-[(4-chlorobenzoyl)amino]phenyl}sulfonyl-L-proline, with a theoretical inhibition constant of IC50 = 4 × 105 M, was constructed on the basis of structural requirements for selective inhibitors of gelatinases. This constructed compound and its close structural analogs were synthesized and these substances were found to have low toxicity, (LD50 > 300 mg/kg). The new inhibitor given p.o. at a dose of 20 mg/kg/day on the background of acute myocardial infarction significantly decreased the content of immunoreactive MMP-9 in plasma in rats, to the level obtained with doxycycline.

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.

Selective hydrogenation dehalogenation method of ortho-halogenated acylaniline

The invention discloses a selective hydrogenation dehalogenation method of copper-catalyzed ortho-halogenated acylaniline. The method comprises the following steps: by using ortho-halogenated acylaniline as a starting raw material and copper acetylacetonate/vasicine as a catalyst, adding an organic alkali, reacting in an alcoholic solution at 80-100 DEG C for 12 hours, and regioselectively catalytically hydrogenating ortho-bromine and iodine atoms. The preparation method has the characteristics of simplicity and convenience in operation, wide substrate application range, low cost, high regioselectivity and the like, and has practicability.

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.

Palladium(II) Complexes of a Neutral CCC-Tris(N-heterocyclic carbene) Pincer Ligand: Synthesis and Catalytic Applications

Treatment of tris-azolium precursor 1 with palladium acetate under thermal conditions provided a CCC-pincer palladium(II) complex (2) bearing three NHCs (one imidazolylidene and two triazolylidenes) and one iodide ligand. Further treatment of complex 2 with an excess of AgSbF6 generates tris(carbene) dicationic palladium complex 3 in which the iodine ligands are exchanged with SbF6 anions and the metal center is stabilized by one acetonitrile ligand. Complexes 2 and 3 were tested in several cross coupling reactions showing high conversions under low catalyst loadings and mild reaction conditions. Additionally, complexes 2 and 3 performed well in the hydrosilylation of terminal alkynes with good selectivity toward the E-isomer.

Regioselective Synthesis of 2° Amides Using Visible-Light-Induced Photoredox-Catalyzed Nonaqueous Oxidative C-N Cleavage of N, N-Dibenzylanilines

A visible-light-driven photoredox-catalyzed nonaqueous oxidative C-N cleavage of N,N-dibenzylanilines to 2° amides is reported. Further, we have applied this protocol on 2-(dibenzylamino)benzamide to afford quinazolinones with (NH4)2S2O8 as an additive. Mechanistic studies imply that the reaction might undergo in situ generation of α-amino radical to imine by C-N bond cleavage followed by the addition of superoxide ion to form amides.

Iron-catalyzed oxidative amidation of acylhydrazines with amines

A new approach for amide bond formation via a mild and efficient Iron-catalyzed cross-coupling reaction of acylhydrazines and amines using TBHP as oxidant is described. This protocol is compatible with a wide range of amines and acylhydrazines. In addition, the synthetic application of the reaction is presented.

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.

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.