3754-53-8

Usage

Molecular Structure

2-(3-Bromophenyl)-4H-chromen-4-one consists of a chromen-4-one core with a bromophenyl group attached to it.

Chemical Classification

It is a chemical compound.

Usage

It is commonly used in organic synthesis and pharmaceutical research as a building block for the preparation of various biologically active compounds.

Potential Applications

It has been studied for its potential as an anti-cancer agent, as well as for its anti-inflammatory and antioxidant properties.

Versatility

Its structure and properties make it a versatile tool for the development of new drugs and therapeutic agents.

Upstream product

• 491-38-3 1-benzopyran-4(4H)-one 
• 89598-96-9 (3-bromophenyl)boronic acid 
• 3754-50-5 3-(3-bromophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one 
• 3132-99-8 m-bromobenzoic aldehyde 
• 118-93-4 o-hydroxyacetophenone 
• 90-02-8 salicylaldehyde 
• 18523-22-3 2,3'-dibromoacetophenone 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 1711-09-7 3-bromobenzoyl chloride 
• 133359-66-7 2,3-dihydro-2-(3-bromophenyl)chromen-4-one 
• 109899-86-7 1-(3-bromophenyl)-3-(2-hydroxyphenyl)propane-1,3-dione 

Downstream Products

• 1375533-45-1 diethyl [2-(3-bromophenyl)-4-oxo-4H-chromen-3-yl]phosphonate 
• 955880-07-6 C₂₁H₂₁BO₄ 

Relevant academic research and scientific papers

Rhodium(III)-catalyzed one-pot synthesis of flavonoids from salicylaldehydes and sulfoxonium ylides

Rh(III)-catalyzed C–H activation of salicylaldehyde followed by an insertion reaction with sulfoxonium ylides and cyclization is applied to the synthesis of flavonoids. This one-pot strategy exhibits good functional group tolerance and gives flavones in moderate-to-good yields.

One-Pot Allan–Robinson/Friedl?nder Route to Chromen-/Quinolin-4-ones through the Domino Acetylative Cyclisation of 2-Hydroxy-/2-Aminobenzaldehydes

The domino synthesis of 2-phenyl-4H-chromen-4-ones and quinolin-4-ones through acetylation of 2-hydroxy-/2-aminobenzaldehydes with α-haloketones followed by intramolecular oxa-/azaheterocyclisation is reported. This method represents a new extension of the Allan–Robinson and Friedl?nder reactions, and uses N-heterocyclic-carbene catalysis to construct the target molecules in good to excellent yields: 86–95 % for the chromen-4-ones, and 83–96 % for the quinolin-4-ones. This approach has the advantages of operational simplicity, ambient reaction conditions, and no by-product formation.

An efficient oxidative conversion of 2-aryl-2H-chromenes to the corresponding flavones by tert-butylhydroperoxide and copper bromide

A simple and efficient method has been developed for the facile oxidation of chromenes to the corresponding flavones by tert-butylhydroperoxide (TBHP) in the presence of copper(II) bromide catalyst in toluene at 80 °C in a very short time. The reaction demonstrates excellent reactivity, functional group tolerance, and good to excellent yields without using conventional strong oxidizing agents.

Gold Nanoparticles Supported on a Layered Double Hydroxide as Efficient Catalysts for the One-Pot Synthesis of Flavones

Flavones are a class of natural products with diverse biological activities and have frequently been synthesized by step-by-step procedures using stoichiometric amounts of reagents. Herein, a catalytic one-pot procedure for the synthesis of flavone and its derivatives is developed. In the presence of gold nanoparticles supported on a Mg-Al layered double hydroxide (Au/LDH), various kinds of flavones can be synthesized starting from 2′-hydroxyacetophenones and benzaldehydes (or benzyl alcohols). The present one-pot procedure consists of a sequence of several reactions, and Au/LDH can catalyze all these different types of reactions. The catalysis is shown to be truly heterogeneous, and Au/LDH can be readily recovered and reused. Go for gold: In the presence of gold nanoparticles supported on a Mg-Al layered double hydroxide (Au/LDH), various flavones were obtained from the corresponding 2′-hydroxyacetophenones and benzaldehydes (or benzyl alcohols). All three (four) steps of this one-pot process are catalyzed by Au/LDH in a truly heterogeneous fashion.

Pyrrolidine and iodine catalyzed domino aldol-Michael-dehydrogenative synthesis of flavones

A one pot synthesis of flavones is established from 2′- hydroxyacetophenones and substituted aromatic aldehydes. The method uses domino aldol-Michael-oxidation reaction catalyzed by pyrrolidine as a base and iodine as an oxidant in dimethyl sulfoxide.

Cyclization of 2'-hydroxychalcones to flavones using ammonium iodide as an iodine source - An eco-friendly approach

Ammonium iodide on exposure to air decomposes to ammonia and iodine. The in situ generated iodine was used for the cyclization of 2'-hydroxychalcones to the corresponding flavones under solvent-free conditions in good to excellent yields. This method could serve as an attractive alternative to the existing methods for synthesis of flavones and the use of toxic molecular iodine is avoided. Copyright

Synthetic approach to flavanones and flavones via ligand-free palladium(ii)-catalyzed conjugate addition of arylboronic acids to chromones

The remarkable catalytic effects of Fe(OTf)3 in the context of the Pd(ii)-catalyzed conjugate addition of arylboronic acids to chromones were observed to yield a variety of flavanones under mild conditions. The addition of catalytic amounts of DDQ and KNO2 to the reactions exclusively yielded flavone analogs. The reaction scope for the transformation was fairly broad, affording good yields of a wide range of flavanones and flavones, which are privileged structures in many biologically active compounds.

Microwave enhanced palladium catalysed coupling reactions: A diversity-oriented synthesis approach to functionalised flavones

Microwave enhanced diversity-oriented synthesis (MEDOS) using palladium catalysed protocols is introduced as a powerful new strategy for the synthesis of systematically modified small molecules and is highlighted by application to functionalised flavones. The Royal Society of Chemistry 2006.

A selective transformation of flavanones to 3-bromoflavones and flavones under microwave irradiation

This paper presents the first report of a highly selective transformation of flavanones to 3-bromoflavones or flavones by microwave irradiation of the corresponding flavanone reactants and N-bromosuccinimide (NBS) in the presence of a catalytic amount of 2,2′-azobis(isobutyronitrile) (AIBN). The combination of good to excellent yields, shorter reaction time (10 min), and high levels of functional group compatibility make this an attractive synthetic approach to 3-bromoflavones and flavones.

USE OF HALO AND/OR NITRO-SUBSTITUTED FLAVONOIDS AS ANXYOLITICS

Methods of treating anxiety with flavonoid compounds according to Formula (I) and dimers thereof, compounds of Formula (I) and dimers thereof, use of compounds of Formula (I) and pharmaceutical formulations comprising flavonoids of Formula (I) and dimers