2650-14-8

Basic information

• Product Name: 3-bromo-2-hydroxy-4H-chromen-4-one
• CAS NO: 2650-14-8
• Molecular Formula: C₉H₅BrO₃
• Molecular Weight: 241.0382
• Mol File: 2650-14-8.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 278.2°C at 760 mmHg
• Flash Point: 122.1°C
• Density: 1.937g/cm³
• Vapor Pressure: 0.00207mmHg at 25°C
• Refractive Index: 1.719
• CAS DataBase Reference: 3-bromo-2-hydroxy-4H-chromen-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-bromo-2-hydroxy-4H-chromen-4-one(2650-14-8)
• EPA Substance Registry System: 3-bromo-2-hydroxy-4H-chromen-4-one(2650-14-8)

Safety Data

• Hazardous Substances Data: 2650-14-8(Hazardous Substances Data)

Usage

General Description

3-bromo-2-hydroxy-4H-chromen-4-one, also known as bromocoumarin, is a chemical compound with the molecular formula C9H5BrO3. It is a derivative of coumarin, which is a natural compound found in various plants and used in the production of perfumes and flavorings. 3-bromo-2-hydroxy-4H-chromen-4-one has a bromine atom attached to the third position of the coumarin ring and a hydroxyl group at the second position, giving it unique chemical properties. 3-bromo-2-hydroxy-4H-chromen-4-one has been studied for its potential biological activities, including antioxidant, anti-inflammatory, and anticancer properties. Additionally, it has been investigated for its potential use in drug development and as a fluorescent probe in biological imaging.

Upstream product

• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 3515-42-2 3-iodo-4-hydroxycoumarin 
• 108-95-2 phenol 
• 86795-49-5 3-(phenyl-λ³-iodanylidene)chromane-2,4-dione 

Downstream Products

• 69538-20-1 3-mercapto-4-hydroxycoumarin 
• 1333150-52-9 3-[(3-chlorophenyl)sulfonyl]-4-hydroxy-2H-chromen-2-one 
• 1333150-53-0 3-[(3-bromophenyl)sulfonyl]-4-hydroxy-2H-chromen-2-one 
• 1071854-84-6 3-[(3-chlorophenyl)thio]-4-hydroxy-2H-chromen-2-one 
• 1333150-46-1 3-[(3-bromophenyl)thio]-4-hydroxy-2H-chromen-2-one 
• 1333150-50-7 4-hydroxy-3-[(3-(trifluoromethyl)phenyl)thio]-2H-chromen-2-one 
• 1071854-86-8 3-[(3-fluorophenyl)thio]-4-hydroxy-2H-chromen-2-one 
• 1333150-48-3 3-[(2-fluorophenyl)thio]-4-hydroxy-2H-chromen-2-one 
• 1333150-47-2 3-[(2-bromophenyl)thio]-4-hydroxy-2H-chromen-2-one 
• 1071854-85-7 4-hydroxy-3-[(3-methoxyphenyl)thio]-2H-chromen-2-one 
• 1333150-51-8 4-hydroxy-3-[(4-(trifluoromethyl)phenyl)thio]-2H-chromen-2-one 
• 1333150-49-4 4-hydroxy-3-([2-(trifluoromethyl)phenyl]thio)-2H-chromen-2-one 
• 18714-37-9 4-hydroxy-3-(phenylsulfanyl)-2H-chromen-2-one 
• 247237-62-3 3-(4-chlorophenylsulfanyl)-4-hydroxy-2H-chromen-2-one 

Relevant articles and documents

Synthesis of: Cis / trans -dihydrochromenones via a photoinduced rearrangement of 4-phenyl-3-aryl/cyclohexenylcoumarins

A concise and environmentally friendly protocol has been developed for the synthesis of cis-dihydrochromenones and trans-dihydrochromenones in EtOH at room temperature. Irradiation of 4-phenyl-3-arylcoumarins in EtOH with 313 nm UV light under an argon atmosphere at room temperature gave cis-4b,15c-dihydro-16H-benzofuro[3′,2′:7,8]phenanthro[9,10-c]chromen-16-ones and cis-8c,14b-dihydro-9H-benzo[11,12]chryseno[5,6-c]chromen-9-ones in good yields. And an analogous treatment of 4-phenyl-3-alkenylcoumarins as 4-phenyl-3-arylcoumarins provided trans-1,2,3,4,4a,14b-hexahydro-5H-phenanthro[9,10-c]chromen-5-ones. The described photorearrangement proceeded smoothly without the addition of any transition metals and additives. The photorearrangement of 4-phenyl-3-arylcoumarins is believed to proceed via 6π-electrocyclization, a [1,3]-hydrogen shift and keto-enol isomerization.

Synthesis of antimicrobial 2,9,10-trisubstituted-6-oxo-7,12-dihydro-chromeno[3,4-b]quinoxalines

A new series of 2,9,10-trisubstituted-6-oxo-7,12-dihydro-chromeno[3,4-b]quinoxalines was synthesized and submitted to antibacterial and antifungal activities. Result of the antimicrobial screening showed the compound 4j being the most effective among the various treatments in antimicrobial screening. Compounds 4c, 4d, 4k, and 4l showed moderate activity against the microorganisms tested.

Convenient Michael addition/β-elimination approach to the synthesis of 4-benzyl- and 4-aryl-selenyl coumarins using diselenides as selenium sources

A concise and efficient, two-step approach toward 4-organoselenyl coumarin derivatives from the easily available 4-hydroxycoumarins, is reported. The synthesis was based on conventional tosylation followed by a tandem selena-Michael addition/β-elimination reaction of an aryl-/benzyl-selenolate anion on the corresponding 4-tosyloxycoumarins. The selenolate anions were conveniently generated in situ by exposure of the corresponding diselenides to NaBH4. Selected compounds demonstrated to exhibit antioxidant properties in mice cortex and hippocampus.

Pd-catalyzed cross-coupling study of bi-functional 3-bromo-4-trifloxycoumarins with triarylbismuth reagents

Abstract The cross-coupling reactions of functionalized 3-bromo-4-trifloxycoumarins have been explored with threefold arylating triarylbismuth reagents. These palladium-catalyzed reactions afforded chemo-selective C-4 arylations with the facile formation of 3-bromo-4-arylcoumarins in good to high yields. Additionally, palladium-catalyzed arylations of functionalized 3-bromo-4-arylcoumarins also participated in the second arylation to give functionalized 3,4-diarylcoumarins in high yields.