1140-36-9

Usage

Uses

Used in Pharmaceutical Industry:
2,1-Benzisoxazole, 3-(4-bromophenyl)is used as a key intermediate in the synthesis of various pharmaceuticals for its versatile reactivity and biological activities. It contributes to the development of new drugs with potential therapeutic benefits.
Used in Agrochemical Industry:
2,1-Benzisoxazole, 3-(4-broMophenyl)is utilized as a building block in the synthesis of agrochemicals, particularly in the development of new pesticides and herbicides, due to its ability to enhance the effectiveness of these products.
Used in Neurodegenerative Disorder Treatment:
2,1-Benzisoxazole, 3-(4-bromophenyl)is used as a potential therapeutic agent for the treatment of neurodegenerative disorders, as it has shown promise in research studies for its ability to target specific enzymes and receptors involved in these conditions.
Used in Enzyme and Receptor Inhibition:
2,1-Benzisoxazole, 3-(4-broMophenyl)serves as an inhibitor of certain enzymes and receptors, making it a valuable tool in the development of drugs that can modulate biological pathways and treat various diseases.
Used in Organic Synthesis:
2,1-Benzisoxazole, 3-(4-bromophenyl)is employed as a building block in the synthesis of organic compounds, contributing to the creation of novel molecules with potential applications in various fields, including materials science and chemical research.

Upstream product

• 108-86-1 bromobenzene 
• 271-58-9 anthranil 
• 106-40-1 4-bromo-aniline 
• 6311-23-5 2-(toluene-4-sulfonylamino)-benzoic acid 
• 525-76-8 2-methyl-4-oxo-3,1-benzoxazine 
• 37892-44-7 2-azido-4'-bromo-benzophenone 
• 1140-17-6 2-amino-4'-bromobenzophenone 
• 118-92-3 anthranilic acid 

Relevant academic research and scientific papers

Metal-Free Synthesis of Anthranils by PhIO Mediated Heterocyclization of ortho-Carbonyl Anilines

Here, we report a metal-free synthesis of anthranils from ortho-carbonyl anilines using PhIO as a sole additive under ambient conditions. This methodology did not require any external additives and delivered anthranils in excellent yields with broad substrate scope. The mechanistic studies suggest that the reaction proceeds via in-situ generation of iminoiodane leading to nitrene and a subsequent nucleophilic attack from oxygen of ortho-carbonyl aniline on nitrene results in heterocyclization.

Metal-Free, Visible-Light-Enabled Direct C3-H Arylation of Anthranils

An eosin Y disodium salt-catalyzed photoredox C-H arylation of anthranils is reported. A variety of aryl diazonium tetrafluoroborates were used as aryl sources, providing the C3 cross-coupled products. The in situ generated reactive radicals were trapped by anthranils, providing an alternative method to transition-metal-catalyzed C-H arylations of anthranils. Gold-catalyzed downstream transformations demonstrate the synthetic potential of these valuable building blocks.

Intramolecular Fe(II)-Catalyzed N-O or N-N bond formation from aryl azides

(Figure presented) Iron(II) bromide catalyzes the transformation of aryl and vinyl azides with ketone or methyl oxime substituents into 2,1-benzisoxazoles, indazoles, or pyrazoles through the formation of an N-O or N-N bond. This transformation tolerates a variety of different functional groups to facilitate access to a range of benzisoxazoles or indazoles. The unreactivity of the Z-methyloxime indicates that N-heterocycle formation occurs through a nucleophilic attack of the ketone or oxime onto an activated planar iron azide complex.

An In-depth Study of the Azidobenzophenone-Anthranil-Acridone Transformation

The title transformation, particularly the conversion of anthranils into acridones, is shown to be critically sensitive to temperature, solvent, substituent, and metal catalysts.Thus the conversion of 3-(p-tolyl)anthranil into an acridone gives a ratio of 2-and 3-methyl derivatives varying from 0.6:1 to 4.7:1 with changing temperature and solvent.In other similar thermolyses, solvents (e.g. 1,2,4-trichlorobenzene) were incorporated into the product and traces of metals and their derivatives had a dramatic effect on the rate and course of the reaction.The most effective catalysts were iron powder and aluminium acetylacetonate. 3-(2,6-Disubstituted phenyl)anthranils gave acridones in which the substituents were either lost or rearranged onto N or C, the last cases involving sequential -sigmatropic shifts. 3-Thienylanthranils gave related thienoquinolones on thermolysis; again the reaction were very sensitive to catalysis.Blocked thienylanthranils also gave rearrangement products, but the non-aromatic intermediates could be isolated.