20525-20-6

Basic information

• Product Name: 4H-1-Benzopyran-4-one,2-(4-bromophenyl)-
• Synonyms: Flavone,4'-bromo- (8CI);4'-Bromoflavone
• CAS NO: 20525-20-6
• Molecular Formula: C₁₅H₉BrO₂
• Molecular Weight: 301.1348
• Product Categories: Pharmaceutical Raw Materials;Mono-substituted Flavones;Bases & Related Reagents;Nucleotides
• Mol File: 20525-20-6.mol

Chemical Properties

• Melting Point: 174-176°C
• Boiling Point: 406.6 °C at 760 mmHg
• Flash Point: 199.7 °C
• Appearance: /
• Density: 1.54 g/cm³
• Vapor Pressure: 8.07E-07mmHg at 25°C
• Refractive Index: 1.656
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly, Sonicated)
• CAS DataBase Reference: 4H-1-Benzopyran-4-one,2-(4-bromophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-4-one,2-(4-bromophenyl)-(20525-20-6)
• EPA Substance Registry System: 4H-1-Benzopyran-4-one,2-(4-bromophenyl)-(20525-20-6)

Safety Data

• Hazardous Substances Data: 20525-20-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4H-1-Benzopyran-4-one,2-(4-bromophenyl)is used as a phase II detoxifying enzyme inducer for promoting the activity of quinone reductase and glutathione S-transferase. These enzymes are crucial in cell culture and different tissues of rats, aiding in the detoxification process and providing potential therapeutic benefits.
Used in Environmental and Toxicology Research:
In the field of environmental and toxicology research, 4H-1-Benzopyran-4-one,2-(4-bromophenyl)is utilized to study the effects of various environmental pollutants and toxins on living organisms. Its role as an inducer of detoxifying enzymes helps researchers understand the mechanisms of cellular defense against harmful substances.
Used in Chemical Synthesis:
4H-1-Benzopyran-4-one,2-(4-bromophenyl)is also used as a key intermediate in the synthesis of various chemical compounds, particularly those with potential applications in the pharmaceutical, agrochemical, and materials science industries. Its unique structure and reactivity make it a valuable building block for the development of new molecules with specific properties and functions.

InChI:InChI=1/C15H9BrO2/c16-11-7-5-10(6-8-11)15-9-13(17)12-3-1-2-4-14(12)18-15/h1-9H

Upstream product

• 118-93-4 o-hydroxyacetophenone 
• 1122-91-4 4-bromo-benzaldehyde 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 22105-04-0 3-(4-bromophenyl)-1-(2-hydroxyphenyl)propan-1-one 
• 1179348-62-9 1-(4-bromophenyl)-2-(2-dimethyl(oxo)-λ⁶-sulfanylidene)ethan-1-one 
• 90-02-8 salicylaldehyde 
• 766-96-1 4-bromo-1-ethynylbenzene 
• 533-58-4 2-Iodophenol 
• 13939-06-5 molybdenum hexacarbonyl 
• 4940-39-0 acide chromone carboxylique-2 
• 5467-74-3 4-Bromophenylboronic acid 
• 934-94-1 1-bromo-4-bromoethynyl-benzene 
• 1393641-92-3 2-(4-bromophenyl)-2H-chromene 
• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 

Downstream Products

• 1132755-70-4 2-(4-bromophenyl)-4H-chromene 
• 1417919-67-5 2-(4'-fluoro-[1,1'-biphenyl]-4-yl)-4H-chromen-4-one 
• 869559-77-3 2-(4'-methyl-biphenyl-4-yl)-chromen-4-one 
• 1417919-71-1 4'-(3''-chlorophenyl)flavone 
• 869559-78-4 2-(4'-chloro-[1,1'-biphenyl]-4-yl)-4H-chromen-4-one 
• 1417919-69-7 4'-(4''-bromophenyl)flavone 
• 869559-76-2 2-(4'-methoxy-biphenyl-4-yl)-chromen-4-one 
• 1417919-68-6 4'-(3''-nitrophenyl)flavone 
• 1417919-72-2 4'-(4''-pyridinyl)flavone 
• 1417919-66-4 4'-(3''-trifluoromethylphenyl)flavone 
• 55736-88-4 4-(4-oxo-4H-chromen-2-yl)benzonitrile 
• 20093-85-0 methyl 4-(4-oxo-4H-chromen-2-yl)benzoate 

Relevant articles and documents

Divergent synthesis of flavones and flavanones from 2′-hydroxydihydrochalconesviapalladium(ii)-catalyzed oxidative cyclization

Divergent and versatile synthetic routes to flavones and flavanonesviaefficient Pd(ii) catalysis are disclosed. These Pd(ii) catalyses expediently provide a variety of flavones and flavanones from 2′-hydroxydihydrochalcones as common intermediates, depending on oxidants and additives,viadiscriminate oxidative cyclization sequences involving dehydrogenation, respectively, in a highly atom-economic manner.

Palladium-Catalyzed Chlorocarbonylation of Aryl (Pseudo)Halides Through In Situ Generation of Carbon Monoxide

An efficient palladium-catalyzed chlorocarbonylation of aryl (pseudo)halides that gives access to a wide range of carboxylic acid derivatives has been developed. The use of butyryl chloride as a combined CO and Cl source eludes the need for toxic, gaseous carbon monoxide, thus facilitating the synthesis of high-value products from readily available aryl (pseudo)halides. The combination of palladium(0), Xantphos, and an amine base is essential to promote this broadly applicable catalytic reaction. Overall, this reaction provides access to a great variety of carbonyl-containing products through in situ transformation of the generated aroyl chloride. Combined experimental and computational studies support a reaction mechanism involving in situ generation of CO.

Temperature-Controlled Stereodivergent Synthesis of 2,2′-Biflavanones Promoted by Samarium Diiodide

In this work, the first example of a radical stereodivergent reaction directed towards the stereoselective synthesis of both (R*,R*)- and (R*,S*)-2,2′-biflavanones promoted by samarium diiodide is reported. Control experiments showed that the selectivity of this reaction was exclusively controlled by the temperature. It was possible to generate a variety of 2,2′-biflavanones bearing different substitution patterns at the aromatic ring in good-to-quantitative yields, being both stereoisomers of the desired compounds obtained with total or high control of selectivity. A mechanism that explains both the generation of the corresponding 2,2′-biflavanones and the selectivity is also discussed. The structure and stereochemistry determination of each isomer was unequivocally elucidated by single-crystal X-ray diffraction experiments.

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.

Regioselective hydrodehalogenation of aromatic α-and β-halo carbonyl compounds by cui in isopropanol

An operationally efficient and regioselective hydrodehalogenation methodology of aromatic α-and β-halo carbonyl compounds has been developed using CuI in isopropanol at 90 °C under basic condition. The catalytic system effectively dehalogenates chloride, bromide, and iodide groups and af-forded high yield (up to 97 %) as carbonyl compounds. The methodology is environmentally friendly and demonstrates excellent tolerance to a broad range of electronically rich and poor substituents.

Iodine-mediated direct synthesis of 3-iodoflavones

Molecular iodine has been used for the regioselective, one pot, direct synthesis of 3-iodoflavones from 2′-allyloxy chalcones, 2′-hydroxy chalcones and flavones. Allyl deprotection, cyclization dehydrogenation and α-iodination of 2′-allyloxychalcones has been achieved in a single step to offer 3-iodoflavones.

Novel and Efficient Access to Flavones under Mild Conditions: Aqueous HI-Mediated Cascade Cyclization/Oxidative Radical Reaction of 2-Propynolphenols

Herein we disclose a metal-free and efficient method for the direct conversion of 2-propynolphenols to biologically important flavones using aqueous HI as the promoter. This transformation was proved via 4-iodo-2H-chromenes intermediate, which was simultaneously conversed to corresponding flavones by a Csp2?I bond cleavage and a C–O bond formation under air.

Carbonylative Sonogashira annulation sequence: One-pot synthesis of 4-quinolone and 4H-chromen-4-one derivatives

Carbonylative Sonogashira annulation sequence for one pot synthesis of 4-quinolone and 4H-chromen-4-one has been developed in presence of Pd-NHC catalyst. Substituted 2-iodoaniline and 2-iodophenol independently underwent in the carbonylative Sonogashira

A transition-metal-free fast track to flavones and 3-arylcoumarins

A highly regioselective and transition-metal free one-pot arylation of chromenones with arylboronic acids has been achieved employing K2S2O8. The procedure consists of a sequence of some reactions including an arylation/decarboxylation cascade and proceeds well in aqueous media to afford biologically interesting flavones and 3-arylcoumarins. This method exhibited excellent selectivity and functional group tolerance under mild conditions. The reaction also showed perfect efficacy for the preparation of styryl coumarins.

Synthesis of 4H-Chromen-4-one Derivatives by Intramolecular Palladium-Catalyzed Acylation of Alkenyl Bromides with Aldehydes

The palladium-catalyzed intramolecular acylation of alkenyl bromides and aldehydes was developed for an efficient synthesis of 4H-chromen-4-ones. With Pd(PPh3)4/Xphos as the catalyst and K2CO3 as the base, this protocol was applied to synthesize a small library of diversely functionalized flavonoids in moderate to good yields in 1,4-dioxane.