1836-27-7

Usage

Uses

Used in Organic Synthesis:
4-bromo-N-hydroxybenzamide is used as a building block in organic synthesis for the creation of more complex molecules, leveraging its ability to form hydrogen bonds with other molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 4-bromo-N-hydroxybenzamide is used as a starting material for the development of new drugs, capitalizing on its anti-inflammatory and antioxidant properties to potentially treat various conditions.
Used in Drug Development:
4-bromo-N-hydroxybenzamide is employed as a potential candidate for drug development due to its therapeutic properties, which include anti-inflammatory and antioxidant effects that could be beneficial in the treatment of a range of diseases and disorders.

Upstream product

• 5798-75-4 Ethyl 4-bromobenzoate 
• 25062-46-8 4-bromobenzaldehyde oxime 
• 873-75-6 4-bromobenzenemethanol 
• 82892-00-0 N-(4-bromobenzoyl)imidazole 
• 586-75-4 4-chlorobenzoyl chloride 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 586-76-5 4-Bromobenzoic acid 

Downstream Products

• 114056-85-8 (4-Bromo-phenyl)-(3-hydroxy-5-methyl-isoxazolidin-2-yl)-methanone 
• 114056-84-7 2-p-bromobenzoyl-3-hydroxyisoxazolidine 
• 130892-08-9 (4-Bromo-phenyl)-(5-hydroxy-isoxazolidin-2-yl)-methanone 
• 132274-24-9 (4-Bromo-phenyl)-(5-hydroxy-3-methyl-isoxazolidin-2-yl)-methanone 
• 71574-02-2 3-(4-bromo-phenyl)-(4ar,7ac)-7,7a-dihydro-4aH-cyclopenta[e][1,4,2]dioxazine 
• 106-40-1 4-bromo-aniline 
• 2493-02-9 4-bromophenyl isocyanate 
• 1225462-92-9 6-bromo-3,4-diphenylisoquinolin-1(2H)-one 
• 1208328-49-7 N-acetoxy-4-bromo-benzamide 
• 1610376-44-7 4-bromo-2-(3,3-dimethylbut-1-yn-1-yl)-N-(pivaloyloxy)benzamide 
• 1610376-35-6 4-bromo-N-(pivaloyloxy)-2-((triisopropylsilyl)ethynyl)benzamide 
• 1428738-13-9 [(ⁿBu)(ⁿHex)Sn{4-bromo-N-hydroxybenzamide}₂] 
• 1429402-22-1 C₁₇H₁₉BrClNO₂Ru 

Relevant academic research and scientific papers

Cu(II)-Catalyzed C-H Amidation/Cyclization of Azomethine Imines with Dioxazolones via Acyl Nitrenes: A Direct Access to Diverse 1,2,4-Triazole Derivatives

We report a Cu(II)-catalyzed C-H amidation/cyclization of azomethine imines with dioxazolones as acyl nitrene transfer reagents under additive-and ligand-free conditions. An array of 1,2,4-triazolo[1,5-a]pyridine derivatives were afforded in moderate to good yields with excellent functional group tolerance. In addition, scale-up reaction and photoluminescence properties were discussed.

Silver-Catalyzed Acyl Nitrene Transfer Reactions Involving Dioxazolones: Direct Assembly of N-Acylureas

Dioxazolones and isocyanides are useful synthetic building blocks, and have attracted significant attention from researchers. However, the silver-catalyzed nitrene transfer reaction of dioxazolones has not been investigated to date. Herein, a silver-catalyzed acyl nitrene transfer reaction involving dioxazolones, isocyanides, and water was realized in the presence of Ag2O to afford a series of N-acylureas in moderate to good yields.

P(III)-Assisted Electrochemical Access to Ureas via in situ Generation of Isocyanates from Hydroxamic Acids

An external oxidant-free protocol for the generation of isocyanates from hydroxamic acids assisted by trivalent phosphine under mild electrochemical conditions was reported. The process started with the anodic oxidation of hydroxamic acids, followed by reacting with phosphine to form corresponding alkoxyphosphoniums and subsequent rearrangement with the release of tri-substituted phosphine oxide as the driving force to give isocyanates, which were trapped by N-based nucleophiles to produce various ureas. This method provides a broadly applicable procedure to access isocyanate intermediates under mild electrochemical conditions.

Palladium-Catalyzed 5-exo-dig Cyclization Cascade, Sequential Amination/Etherification for Stereoselective Construction of 3-Methyleneindolinones

An cascade intramolecular 5-exo-dig cyclization of N-(2-iodophenyl)propiolamides and sequential amination/etherification (with N-hydroxybenzamides, phenyl hydroxycarbamate) protocol for the synthesis of amino- and phenoxy-substituted 3-methyleneindolinones using unexpensive Pd(PPh3)4 as catalyst has been developed. The protocol enables the assembly of structurally important oxindole cores featuring moderate functional group tolerance (particularly the halo group), affording a broad spectrum of products with diverse substituents in good to excellent yields. (Figure presented.).

Synthesis of sulfimides and N-Allyl-N-(thio)amides by Ru(II)catalyzed nitrene transfer reactions of N-acyloxyamides

The N-acyloxyamides were employed as effective N-acyl nitrene precursors in reactions with thioethers under the catalysis of a commercially available Ru(II) complex, from which a variety of sulfimides were synthesized efficiently and mildly. If an allyl group is contained in the thioether precursor, the [2,3]-sigmatropic rearrangement of the sulfimide occurs simultaneously and the N-allyl-N-(thio)amides were obtained as the final products. Preliminary mechanistic studies indicated that the Ru-nitrenoid species should be a key intermediate in the transformation.

Stepwise Evolution of Fragment Hits against MAPK Interacting Kinases 1 and 2

Dysregulation of translation initiation factor 4E (eIF4E) activity occurs in various cancers. Mitogen-activated protein kinase (MAPK) interacting kinases 1 and 2 (MNK1 and MNK2) play a fundamental role in activation of eIF4E. Structure-activity relationship-driven expansion of a fragment hit led to discovery of dual MNK1 and MNK2 inhibitors based on a novel pyridine-benzamide scaffold. The compounds possess promising in vitro and in vivo pharmacokinetic profiles and show potent on target inhibition of eIF4E phosphorylation in cells.

Palladium-catalyzed cascade decarboxylative amination/6- endo-dig benzannulation of o-alkynylarylketones with n-hydroxyamides to access diverse 1-naphthylamine derivatives

An efficient and practical one-pot strategy to produce highly substituted 1-naphthylamines via sequential palladium-catalyzed decarboxylative amination/intramolecular 6-endo-dig benzannulation reactions has been described. In this reaction, a broad range of electron-rich, electron-neutral, and electron-deficient o-alkynylarylketones react well with N-hydroxyl aryl/alkylamides to give a diversity of 1-naphthylamines in good to excellent yields under mild reaction conditions. The gram-scale synthesis, with benefits such as undiminished product yield and easy transformation, illustrated the practicality of this method.

Divergent Synthesis of Tunable Cyclopentadienyl Ligands and Their Application in Rh-Catalyzed Enantioselective Synthesis of Isoindolinone

A series of rhodium complexes bearing sterically and electronically tunable cyclopentadienyl ligands, prepared by utilizing Co2(CO)8-mediated [2+2+1] cyclization as a key step, were synthesized. In the presence of 2.5 mol% of CpmRh4, unprecedented enantioselective [4+1] annulation reaction of benzamides and alkenes was achieved with a broad substrate scope under mild reaction conditions, providing a variety of isoindolinones with excellent regio-and enantioselectivity (up to 94% yield, 97:3 er). Preliminary mechanistic studies suggest that the reaction involves an oxidative Heck reaction and an intramolecular enantioselective alkene hydroamination reaction.

RhIII-Catalyzed C?H Activation of Aryl Hydroxamates for the Synthesis of Isoindolinones

RhIII-catalyzed C?H functionalization reaction yielding isoindolinones from aryl hydroxamates and ortho-substituted styrenes is reported. The reaction proceeds smoothly under mild conditions at room temperature, and tolerates a range of functional groups. Experimental and computational investigations support that the high regioselectivity observed for these substrates results from the presence of an ortho-substituent embedded in the styrene. The resulting isoindolinones are valuable building blocks for the synthesis of bioactive compounds. They provide easy access to the natural-product-like compounds, isoindolobenzazepines, in a one-pot two-step reaction. Selected isoindolinones inhibited Hedgehog (Hh)-dependent differentiation of multipotent murine mesenchymal progenitor stem cells into osteoblasts.

Rhodium(III)-catalyzed C4-amidation of indole-oximes with dioxazolones: Via C-H activation

A novel method for the Rh(III)-catalyzed oxime-directed C-H amidation of indoles with dioxazolones has been developed. This strategy provides an exclusive site selectivity and the directing group can be easily removed. This transformation features a wide substrate scope, good functional group tolerance and excellent yields, and may serve as a significant tool to construct structurally diverse indole derivatives for the screening of potential pharmaceuticals in the future. This journal is