146900-52-9

Basic information

• Product Name: 2H-1-Benzopyran-2-one, 3-bromo-7-hydroxy-
• Synonyms: 3-bromo-7-hydroxycoumarin;3-bromo-7-hydroxy-2H-1-benzopyran-2-one;3-BROMO-7-HYDROXY-2H-CHROMEN-2-ONE;3-bromoumbelliferone;3-Brom-umbelliferon;2H-1-Benzopyran-2-one,3-bromo-7-hydroxy
• CAS NO: 146900-52-9
• Molecular Formula: C9H5BrO3
• Molecular Weight: 241.03800
• Mol File: 146900-52-9.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: 2H-1-Benzopyran-2-one, 3-bromo-7-hydroxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-1-Benzopyran-2-one, 3-bromo-7-hydroxy-(146900-52-9)
• EPA Substance Registry System: 2H-1-Benzopyran-2-one, 3-bromo-7-hydroxy-(146900-52-9)

Safety Data

• Hazardous Substances Data: 146900-52-9(Hazardous Substances Data)

Upstream product

• 93-35-6 7-hydroxy-2H-chromen-2-one 
• 10387-49-2 7-acetyloxycoumarin 
• 72167-80-7 3-bromo-7-methoxy-2H-chromen-2-one 
• 531-59-9 7-methoxycoumarin 
• 15481-39-7 dioxane dibromide 

Downstream Products

• 72167-80-7 3-bromo-7-methoxy-2H-chromen-2-one 
• 1386897-94-4 3-[4-(7-hydroxycoumarin-3-ylethynyl)phenyl]propanoic acid 
• 1361199-23-6 3-([1,1'-biphenyl]-4-yl)-7-((1-methylpiperidin-4-yl)oxy)-2H-chromen-2-one 
• 1361199-22-5 3-([1,1'-biphenyl]-2-yl)-7-((1-methylpiperidin-4-yl)oxy)-2H-chromen-2-one 
• 1361199-21-4 3-(4-(tert-butyl)phenyl)-7-((1-methylpiperidin-4-yl)oxy)-2H-chromen-2-one 
• 1361199-20-3 7-((1-methylpiperidin-4-yl)oxy)-3-(4-phenoxyphenyl)-2H-chromen-2-one 
• 1361199-18-9 3-(3-fluorophenyl)-7-((1-methylpiperidin-4-yl)oxy)-2H-chromen-2-one 
• 1361199-17-8 3-(4-fluorophenyl)-7-((1-methylpiperidin-4-yl)oxy)-2H-chromen-2-one 
• 1361199-16-7 3-(7-((1-methylpiperidin-4-yl)oxy)-2-oxo-2H-chromen-3-yl)benzonitrile 
• 1361199-15-6 7-((1-methylpiperidin-4-yl)oxy)-3-(4-(trifluoromethoxy)phenyl)-2H-chromen-2-one 
• 1361199-13-4 7-((1-methylpiperidin-4-yl)oxy)-3-(3-(trifluoromethyl)phenyl)-2H-chromen-2-one 
• 1361199-11-2 3-(4-methoxyphenyl)-7-((1-methylpiperidin-4-yl)oxy)-2H-chromen-2-one 
• 1361199-09-8 7-((1-methylpiperidin-4-yl)oxy)-3-(p-tolyl)-2H-chromen-2-one 
• 1361199-07-6 3-(4-chlorophenyl)-7-((1-methylpiperidin-4-yl)oxy)-2H-chromen-2-one 

Relevant articles and documents

An efficient regioselective bromination protocol of activated coumarins using 2,4,4,6-tetrabromo-2,5-cyclohexadienone

2,4,4,6-Tetrabromo-2,5-cyclohexadienone mediated bromination of a wide assortment of activated coumarins in acetonitrile has been accomplished with high regioselectivity and good to excellent yields. The selectivity and efficiency of bromination were found to be markedly dependent on electronic factors, particularly degree of electron withdrawal from electron-releasing 7-oxygenated substituents to the C-3 position of the α-pyrone moiety by vinylogous resonance and the presence of nucleophilic additives such as water and tetra-n-butylammonium bromide in the reaction medium. The sole by-product of the reaction was converted back to the reagent by oxidation with KBr-KBrO 3, which was recycled three times without significant loss of efficiency.

A Copper Halide Promoted Regioselective Halogenation of Coumarins Using N-Halosuccinimide as Halide Source

A safe, convenient, and regioselective synthesis of 3-halo coumarins using a metal halide (CuX 2 alone or with ZnX 2) promoted halogenation with N -halosuccinimide (NXS) as halide source is reported. The synthesis involved the steady in situ generation of highly reactive positive halogen (X +) by the coordination of copper or zinc with the N -halosuccinimide and subsequent electrophilic aromatic substitution of the electron-deficient coumarins. This procedure works well also for the halogenation of less electron-rich naphthoquinones, flavones, and methoxypsoralen in moderate to quantitative yields. This protocol features simple experimental conditions using readily available inexpensive reagents and provides a convenient approach to the chlorination or bromination of some useful heteroaromatic compounds.

3-arylcoumarin derivatives manifest anti-proliferative activity through Hsp90 inhibition

The potential therapeutic benefits associated with Hsp90 modulation for the treatment of cancer and neurodegenerative diseases highlight the importance of identifying novel Hsp90 scaffolds. KU-398, a novobiocin analogue, and silybin were recently identified as new Hsp90 inhibitors. Consequently, a library of 3-arylcoumarin derivatives that incorporated the structural features of KU-398 and silybin was designed, synthesized, and evaluated against two breast cancer cell lines. Western blot analysis confirmed that the resulting 3-arylcoumarin hybrids target the Hsp90 protein folding machinery.