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Usage

Uses

Used in Organic Synthesis:
(5,7-DIBROMO-1-BENZOFURAN-2-YL)(PHENYL)METHANONE is used as a building block in organic synthesis for the creation of various biologically active molecules. Its unique structure and reactivity make it a valuable component in the development of new compounds with potential applications across different industries.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (5,7-DIBROMO-1-BENZOFURAN-2-YL)(PHENYL)METHANONE is utilized as a key intermediate for the synthesis of pharmaceuticals. Its properties allow for the development of new drugs with improved efficacy and targeted action against specific diseases.
Used in Agrochemicals:
(5,7-DIBROMO-1-BENZOFURAN-2-YL)(PHENYL)METHANONE is also employed in the agrochemical industry as a starting material for the synthesis of various agrochemical products, such as pesticides and herbicides, that are designed to enhance crop protection and yield.
Used in Materials Science:
(5,7-DIBROMO-1-BENZOFURAN-2-YL)(PHENYL)METHANONE has potential applications in materials science, where its unique properties can be harnessed to develop new materials with specific characteristics, such as improved strength, durability, or chemical resistance.
Used in the Study of Organic Reactions:
(5,7-DIBROMO-1-BENZOFURAN-2-YL)(PHENYL)METHANONE serves as a valuable tool in the study of organic reactions, providing insights into reaction mechanisms and helping to develop new synthetic methods and techniques.

Upstream product

• 90-59-5 3,5-Dibromosalicylaldehyde 
• 19738-76-2 3,5-dibromo-2-hydroxychalcone dibromide 
• 25726-04-9 phenylglyoxylyl chloride 
• 89266-25-1 3,5-Dibrom-2-hydroxybenzyltriphenylphosphoniumbromid 
• 67-56-1 methanol 
• 644-78-0 2-hydroxychalcone 
• 55210-75-8 2-((E)-3-oxo-3-phenylprop-1-en-1-yl)phenyl acetate 
• 136068-46-7 3,5-dibromo-2-hydroxy-trans-chalcone 
• 98-86-2 acetophenone 
• 70-11-1 α-bromoacetophenone 

Downstream Products

• 477848-45-6 (5,7-dibromo-benzofuran-2-yl)-phenyl ketone oxime 
• 83806-48-8 (5,7-Dibromo-benzofuran-2-yl)-phenyl-methanol 

Relevant academic research and scientific papers

Synthesis and anti-methicillin-resistant Staphylococcus aureus activity of 5,7-dibromo-2-benzoylbenzofurans alone and in combination with antibiotics

A series of 5,7-dibromo-2-benzoylbenzofurans were synthesized by the Rap–Stoermer condensation of 5,7-dibromosalicylaldehyde with diverse phenacyl bromides and evaluated for in-vitro antibacterial activities against methicillin-sensitive Staphylococcus aureus (MSSA) ATCC 29213, methicillin-resistant Staphylococcus aureus (MRSA) ATCC 43300, and MRSA ATCC 33591 by agar dilution method. The synergistic effects were determined by using the agar dilution checkerboard assay. The derivatives bearing carboxylic acid functional groups exhibited reasonable activity against MRSA strains with the best MIC = 32 μg/mL (9b, 9d). Moreover, the additive or synergistic interactions against MRSA strains was observed in six combinations (1b + cefuroxime/gentamicin, 1c + ciprofloxacin/gentamicin, 9b + gentamicin, and 9c + ciprofloxacin) with the fractional inhibitory concentration index (FICI) values in the range of 0.375–1.0. Significantly, the MICs of these antibiotics were reduced 2–4-fold. The results of the MTT assay illustrated the low mammalian cell cytotoxicity of these potent compounds.

Intramolecular oxidative coupling: I2/TBHP/NaN3-mediated synthesis of benzofuran derivatives

A novel intramolecular oxidative coupling reaction has been established to prepare benzofuran derivatives via direct C(sp2)-H functionalization for the formation of C-O bond. This transformation is mediated by I2/TBHP/NaN3 under metal-free conditions and a catalytic amount of NaN3 plays a crucial role in the reaction. Furthermore, the reaction tolerates a broad substrate scope with average to excellent yields.

Microwave-mediated solvent free Rap-Stoermer reaction for efficient synthesis of benzofurans

The Rap-Stoermer reaction of salicylaldehydes with diverse phenacyl bromide and phenacyl iodides proceeded cleanly to afford various functionalized benzofurans in excellent yields under base-mediated solvent free microwave irradiation conditions.

Reaction of chalcones with NBS, a simple one pot synthesis of 2-aroylbenzo[b]furanes

A simple one pot synthesis of 2-aroylbenzo[b]furanes has been achieved by bromomethoxylation with NBS and subsequent treatment of the appropriately substituted 2-hydroxychalcones with sodium hydroxide.

New Syntheses of 2-Acylbenzofurans, 2-Acylindoles, 2-Indolylcarboxylates, and 2-Quinolones by Intramolecular Wittig Reaction

The title compounds are obtained by intramolecular Wittiig reaction of 2-(α-ketoacyloxy)-, 2-(α-ketoacylamino)-, or 2-benzyltriphenylphosphonium salts, respectively.

Pyrolitic Elimination of Hydrogen Halide and Halogen from 2,3-Dihalogenoketones

The thermal elimination of hydrogen chloride from 2'-hydroxychalcone dichlorides occured in two stages, initially forming 3-chloroflavones and then flavones; α-chloro-2'-hydroxychalcones, the likely intermediates in the formation of 3-chloroflavones, also yielded the same products.The pyrolysis of 2'-hydroxychalcone dibromides resulted in debromination as well as dehydrobromination with the consequent appearence of brominated flavones among the products.The formation of 3-bromoflavones was not observed but the isomeric (E)-α-bromo-2'-hydroxychalcones thermally isomerized to their (Z)-isomers and then underwent cyclization and dehydrobromination.The bromide were considerably more reactive than the dichlorides but, as a synthetic procedure, the pyrolysis of the dichlorides is cleaner and more productive.