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

Downstream Products

• 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 
• 1361199-05-4 3-(3-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.

Dioxane dibromide mediated bromination of substituted coumarins under solvent-free conditions

An efficient solvent-free protocol for regioselective bromination of substituted coumarins has been developed by using dioxane dibromide as the solid brominating agent. The efficacy of the solvent-free protocol has been established. The effects of the electronic nature and location of the substituents on the outcome of the reaction have been rationalized with a proposed mechanism.