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
• Article Data: 38

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

Description

4H-1-Benzopyran-4-one,2-(4-bromophenyl)-, also known as 4'-Bromoflavone, is a white to off-white crystalline solid with chemical properties that make it a valuable compound in various applications. It is an aryl hydrocarbon hydroxylase inducer, which plays a significant role in the detoxification process.

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

• 17255-67-3 2-(4-bromophenyl)chroman-4-one 
• 66406-65-3 4-bromo-2'-hydroxychalcone dibromide 
• 65786-14-3 (2E)-3-(4-bromophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one 
• 930-69-8 sodium thiophenolate 
• 81281-77-8 Methanesulfonic acid (2R,3R)-2-(4-bromo-phenyl)-4-oxo-chroman-3-yl ester 
• 109899-87-8 1-(4'-bromophenyl)-3-(2-hydroxyphenyl)propane-1,3-dione 
• 118-93-4 o-hydroxyacetophenone 
• 586-75-4 4-chlorobenzoyl chloride 
• 1122-91-4 4-bromo-benzaldehyde 
• 65786-14-3 4-bromo-2'-hydroxylchalcone 
• 766-96-1 4-bromo-1-ethynylbenzene 
• 533-58-4 2-Iodophenol 
• 201230-82-2 carbon monoxide 
• 491-38-3 1-benzopyran-4(4H)-one 

Downstream Products

• 955880-08-7 2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-chromen-4-one 
• 41255-19-0 2-([1,1′-biphenyl]-4-yl)-4H-chromen-4-one 
• 20081-60-1 2'-phenyl-2,6'-p-phenylene-bis-chromen-4-one 
• 1132755-70-4 2-(4-bromophenyl)-4H-chromene 
• 1184291-43-7 diethyl [2-(4-bromophenyl)-4-oxo-4H-chromen-3-yl]phosphonate 
• 1417919-73-3 4'-(2''-furanyl)flavone 
• 1417919-74-4 4'-(3'''-thienyl)flavone 
• 1417919-70-0 4-(4''-vinylphenyl)flavone 
• 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 

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.

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.

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.