1218-80-0

Basic information

• Product Name: 6-BROMOFLAVONE
• Synonyms: 6-BROMOFLAVONE;6-BROMO-2-PHENYL-4H-CHROMEN-4-ONE;6-bromo-2-phenyl-(4h)-4-benzopyranone;6-Bromo-2-phenyl-4H-1-benzopyran-4-one, 6-Bromoflavone;6-Bromo-2-phenyl-(4H)-4-benzopyranone 97%
• CAS NO: 1218-80-0
• Molecular Formula: C₁₅H₉BrO₂
• Molecular Weight: 301.13
• Mol File: 1218-80-0.mol
• Article Data: 35

Chemical Properties

• Melting Point: 193-196 °C(lit.)
• Boiling Point: 421.1 °C at 760 mmHg
• Flash Point: 208.5 °C
• Appearance: /
• Density: 1.54 g/cm³
• Vapor Pressure: 2.67E-07mmHg at 25°C
• Refractive Index: 1.656
• CAS DataBase Reference: 6-BROMOFLAVONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMOFLAVONE(1218-80-0)
• EPA Substance Registry System: 6-BROMOFLAVONE(1218-80-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 1218-80-0(Hazardous Substances Data)

Usage

Description

6-Bromo-2-phenyl-(4H)-4-benzopyranone, commonly known as 6-bromoflavone, is a mononuclear halogenated flavone derived from flavanone through a bromination process. It can also be synthesized from 2′-hydroxychalcone dibromide. 6-BROMOFLAVONE holds potential applications in various fields due to its unique chemical structure and properties.

Uses

Used in Pharmaceutical Industry:
6-Bromoflavone is used as a pharmaceutical compound for its potential therapeutic effects. It has been studied for its possible role in treating various diseases and conditions, including its antioxidant, anti-inflammatory, and anti-cancer properties. The bromine atom in its structure may contribute to its biological activity, making it a valuable candidate for drug development.
Used in Chemical Synthesis:
In the field of organic chemistry, 6-bromoflavone serves as a key intermediate in the synthesis of more complex molecules and compounds. Its bromine atom can be replaced with other functional groups, allowing for the creation of a wide range of derivatives with diverse applications.
Used in Research and Development:
6-Bromoflavone is utilized as a research tool in the study of flavonoids and their biological activities. It can help scientists understand the structure-activity relationships of flavones and their potential applications in medicine and other industries.
Used in Material Science:
The unique properties of 6-bromoflavone, such as its halogenated structure, may find applications in the development of new materials with specific characteristics, such as improved stability or enhanced optical properties.

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

Upstream product

• 487-26-3 Flavanone 
• 525-82-6 FLAVONE 
• 51483-92-2 6-bromo-1-benzopyran-4(4H)-one 
• 98-80-6 phenylboronic acid 
• 51484-06-1 6-bromo-4-oxo-4H-chromene-2-carboxylic acid 
• 4079-51-0 1-(3-bromophenyl)-2-hydroxyethan-1-one 
• 100-52-7 benzaldehyde 
• 1450-75-5 5-Bromo-2-hydroxyacetophenone 
• 65-85-0 benzoic acid 
• 698-88-4 (2,2-dichlorovinyl)benzene 
• 1761-61-1 5-bromosalicyclaldehyde 
• 109619-11-6 1-(5-bromo-2-hydroxyphenyl)-3-phenylprop-2-yn-1-one 
• 1218-22-0 (E)-1-(5-bromo-2-hydroxyphenyl)-3-phenylprop-2-en-1-one 
• 22966-26-3 1-(3-bromophenyl)-3-phenylprop-2-en-1-one 

Downstream Products

• 65-85-0 benzoic acid 
• 1393811-60-3 (E)-6-styrylflavone 
• 1393811-61-4 (E)-6-(4-methylstyryl)flavone 
• 1393811-62-5 (E)-6-(4-methoxystyryl)flavone 
• 1393811-63-6 (E)-6-(4-chlorostyryl)flavone 
• 1393811-64-7 (E)-6-(3-hydroxy-3-methylbut-1-enyl)flavone 
• 1393811-65-8 ethyl (E)-6-(2-phenyl-4-oxo-4H-1-benzopyran-3-yl)acrylate 
• 6665-83-4 6-hydroxyflavone 

Relevant articles and documents

N-Benzylation of 6-aminoflavone by reductive amination and efficient access to some novel anticancer agents via topoisomerase II inhibition

Series of novel N-benzyl derivatives of 6-aminoflavone (9a–n) were synthesized and evaluated for anticancer and topoisomerase II enzyme inhibition activity. All the synthesized compounds were screened for in vitro anticancer activity against human breast cancer cell line (MCF-7) and human lung cancer cell line (A-549). Among the synthesized compounds, 9f and 9g were found to be the most potent anticancer agents against human breast cancer cell line (MCF-7) with IC50 values of 9.35?μM and 9.58?μM, respectively. Compounds 9b, 9c and 9n exhibited promising anticancer activity against human lung cancer cell line (A-549) with 43.71%, 46.48% and 44.26% inhibition at the highest concentration of 10?μM, respectively. Compounds 9c, 9f and 9g have ability to inhibit the topoisomerase II enzyme. Compound 9f showed most potent topoisomerase II enzyme inhibition activity with IC50 value of 12.11?μM. Further, these compounds have a high potential to be developed as a promising topoisomerase II inhibitors.

Microwave assisted efficient synthesis of flavone using ZnO nanoparticles as promoter under solvent-free conditions

A simple and highly efficient protocol for synthesis of flavones from 1-(2-hydroxyphenyl)-3-aryl-1,3-propanediones in presence of ZnO nanoparticles as a promoter in thermal as well as microwave irradiation under solvent-free conditions have been demonstrated. The catalyst is inexpensive, stable, can be easily recycled/reused for several cycles with consistent activity and observed almost same yield confirming the stability of the catalyst. It is believed that the present approach will become an alternative route for the conventional reactions. Because in this protocol, yield is quite high, short reaction time, simple work up, catalyst can be recycled as well as it is free of any hazardous by-products formation during workup.

Synthesis of Phenols: Organophotoredox/Nickel Dual Catalytic Hydroxylation of Aryl Halides with Water

A highly effective hydroxylation reaction of aryl halides with water under synergistic organophotoredox and nickel catalysis is reported. The OH group of the resulting phenols originates from water, following deprotonation facilitated by an intramolecular base group on the ligand. Significantly, aryl bromides as well as less reactive aryl chlorides served as effective substrates to afford phenols with a wide range of functional groups. Without the need for a strong inorganic base or an expensive noble-metal catalyst, this process can be applied to the efficient preparation of diverse phenols and enables the hydroxylation of multifunctional pharmaceutically relevant aryl halides.