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

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

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 
• 854651-24-4 1-(5-bromo-2-methoxy-phenyl)-3-phenyl-propane-1,3-dione 
• 525-82-6 FLAVONE 
• 39729-11-8 2'-hydroxychalcone dibromides 
• 109619-14-9 (Z)-1-(5-Bromo-2-hydroxy-phenyl)-3-phenyl-3-phenylamino-propenone 
• 5067-24-3 1-(5-bromo-2-hydroxyphenyl)-3-phenyl-1,3-propanedione 
• 1450-75-5 5-Bromo-2-hydroxyacetophenone 
• 98-88-4 benzoyl chloride 
• 536-74-3 phenylacetylene 
• 4010-28-0 5'-bromo-2'-benzoyloxy-acetophenone 
• 1218-22-0 3-phenyl-1-(2'-hydroxy-5'-bromophenyl)-2-propen-1-one 
• 100-52-7 benzaldehyde 
• 22966-26-3 1-(3-bromophenyl)-3-phenylprop-2-en-1-one 
• 109619-11-6 1-(5-bromo-2-hydroxyphenyl)-3-phenylprop-2-yn-1-one 

Downstream Products

• 107917-81-7 3,6-dibromo-Flavone 
• 65-85-0 benzoic acid 
• 955880-06-5 2-Phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4Hchromen-4-one 
• 20081-46-3 6,6''-biflavone 
• 1446428-62-1 7-ethynyl-2-phenyl-4H-chromen-4-one 
• 1446428-55-2 6-(2-phenylethynyl)flavone 
• 1446428-56-3 6-(2-(trimethylsilyl)ethynyl)flavone 
• 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.

Discovery of Novel Dual-Target Inhibitor of Bromodomain-Containing Protein 4/Casein Kinase 2 Inducing Apoptosis and Autophagy-Associated Cell Death for Triple-Negative Breast Cancer Therapy

Bromodomain-containing protein 4 (BRD4) is an attractive epigenetic target in human cancers. Inhibiting the phosphorylation of BRD4 by casein kinase 2 (CK2) is a potential strategy to overcome drug resistance in cancer therapy. The present study describes the synthesis of multiple BRD4–CK2 dual inhibitors based on rational drug design, structure–activity relationship, and in vitro and in vivo evaluations, and 44e was identified to possess potent and balanced activities against BRD4 (IC50 = 180 nM) and CK2 (IC50 = 230 nM). In vitro experiments show that 44e could inhibit the proliferation and induce apoptosis and autophagy-associated cell death of MDA-MB-231 and MDA-MB-468 cells. In two in vivo xenograft mouse models, 44e displays potent anticancer activity without obvious toxicities. Taken together, we successfully synthesized the first highly effective BRD4–CK2 dual inhibitor, which is expected to be an attractive therapeutic strategy for triple-negative breast cancer (TNBC).

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.

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.

A 2 - aryl flavone preparation method

The invention discloses a 2 - aryl flavone preparation method, including: in the silver catalyst and under the action of the oxidizing agent, ortho-hydroxy aryl formyl formic acid and aryl alkynoic ring reaction in a solvent, after the reaction is finished after treatment to obtain the 2 - aryl flavone. The method of this invention easily obtained and cheap agents, mild reaction conditions, reaction functional group compatibility is good, cheap catalyst, the catalytic system is simple.

One Pot Synthesis of γ-Benzopyranones via Iron-Catalyzed Aerobic Oxidation and Subsequent 4-Dimethylaminopyridine Catalyzed 6-endo Cyclization

One-pot synthesis of γ-benzopyranones was realized in decent yields and excellent regioselectivities via iron-catalyzed aerobic oxidation and 4-dimethylaminopyridine-catalyzed cyclization of related propargylic alcohols. Derivatizations to aromatic substituted γ-benzopyranones and synthesis of naturally occurring 3′,4′-dimethoxyflavone have also been realized. (Figure presented.).

One-pot Synthesis of Aurones through Oxidation-cyclization Tandem Reaction Catalyzed by Copper Nanoparticles Catalyst

Aurones were synthesized through an oxidation-cyclization tandem reaction of 2-(1- hydroxyprop-2-ynyl)phenols catalyzed by copper nanoparticles (Cu NPs) with bipyridine as the ligand. In the reaction, oxygen worked as a green and mild oxidant to give the best results. Cu NPs were dually activated by bipyridine ligand and water, and showed highly efficient catalytic activities to the oxygen oxidation and the cylization to give aurones and flavonoids.

Silver-catalyzed Double Decarboxylative Radical Alkynylation/Annulation of Arylpropiolic Acids with α-keto Acids: Access to Ynones and Flavones under Mild Conditions

Ynones are privileged building blocks in various organic syntheses of heterocyclic derivatives due to their multifunctional nature, and flavones are an important class of natural products with a wide range of biological activities. We describe the catalytic double decarboxylative alkynylation of arylpropiolic acids with α-keto acids. With Ag(I)/persulfate as the catalysis system, the valuable ynones bearing various substituents could be easily obtained. The introduction of hydroxyl substituent on ortho-site of α-keto acids make this strategy further applicable to the construction of flavone derivatives via heteroannulation in moderate to good yields with a similar silver-catalyzed system. The reactions proceed under relatively mild reaction conditions and tolerate a wide variety of functional groups. Control experiments indicated that both the reactions undergo radical processes. (Figure presented.).

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.

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.