55977-10-1

Basic information

• Product Name: 3-BROMO-7-HYDROXY-4-METHYLCHROMEN-2-ONE
• Synonyms: 3-BROMO-7-HYDROXY-4-METHYLCHROMEN-2-ONE;3-BROMO-7-HYDROXY-4-METHYLCHROMEN-2-ONE, 95+%;3-broMo-7-hydroxy-4-Methyl-2H-chroMen-2-one
• CAS NO: 55977-10-1
• Molecular Formula: C₁₀H₇BrO₃
• Molecular Weight: 255.06
• Mol File: 55977-10-1.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 422.9 °C at 760 mmHg
• Flash Point: 209.6 °C
• Appearance: /
• Density: 1.748g/cm³
• Vapor Pressure: 9.45E-08mmHg at 25°C
• Refractive Index: 1.664
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 3-BROMO-7-HYDROXY-4-METHYLCHROMEN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMO-7-HYDROXY-4-METHYLCHROMEN-2-ONE(55977-10-1)
• EPA Substance Registry System: 3-BROMO-7-HYDROXY-4-METHYLCHROMEN-2-ONE(55977-10-1)

Safety Data

• Hazardous Substances Data: 55977-10-1(Hazardous Substances Data)

Usage

Preparation

Synthesis of 3-bromo-7-hydroxy-4-methyl-2H-chromen-2-one: 4-Methyl-7-hydroxy coumarin was added to acetic acid and stirred for 40 min. Potassium bromate was added to the reaction mixture stirred for 90 min to dissolve completely. Potassium bromide was charged and further stirred for 2 h. The reaction mixture was poured into cold water and stirred for half an hour, filtered and washed with water and recrystallized using ethanol.

InChI:InChI=1/C10H7BrO3/c1-5-7-3-2-6(12)4-8(7)14-10(13)9(5)11/h2-4,12H,1H3

Upstream product

• 75908-67-7 3-bromo-7-methoxy-4-methylcoumarin 
• 2555-28-4 4-methyl-7-methoxy-2H-1-benzopyran-2-one 
• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 15481-39-7 dioxane dibromide 
• 848850-50-0 7-triisopropylsilyloxy-4-methylcoumarin 
• 848850-51-1 3-bromo-4-methyl-7-triisopropylsilanyloxy-chromen-2-one 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 84911-18-2 ethyl 2-bromoacetoacetate 
• 108-46-3 recorcinol 

Downstream Products

• 1227925-70-3 3-bromo-4-methyl-7-(2-oxo-2-phenyl-ethoxy)-chromen-2-one 

Relevant articles and documents

Discovery of Potent Coumarin-Based Kinetic Stabilizers of Amyloidogenic Immunoglobulin Light Chains Using Structure-Based Design

In immunoglobulin light-chain (LC) amyloidosis, transient unfolding or unfolding and proteolysis enable aggregation of LC proteins, causing potentially fatal organ damage. A drug that kinetically stabilizes LCs could suppress aggregation; however, LC sequences are variable and have no natural ligands, hindering drug development efforts. We previously identified high-throughput screening hits that bind to a site at the interface between the two variable domains of the LC homodimer. We hypothesized that extending the stabilizers beyond this initially characterized binding site would improve affinity. Here, using protease sensitivity assays, we identified stabilizers that can be divided into four substructures. Some stabilizers exhibit nanomolar EC50 values, a 3000-fold enhancement over the screening hits. Crystal structures reveal a key π-πstacking interaction with a conserved tyrosine residue that was not utilized by the screening hits. These data provide a foundation for developing LC stabilizers with improved binding selectivity and enhanced physicochemical properties.

1,2,3,4-Tetrahydroisoquinoline/2H-chromen-2-one conjugates as nanomolar P-glycoprotein inhibitors: Molecular determinants for affinity and selectivity over multidrug resistance associated protein 1

A series of coniugates bearing a 1,2,3,4-tetrahydroisoquinoline motif linked to substituted 7-hydroxy-2H-chromen-2-ones was synthesized and assayed through calcein-AM test in Madin-Darby Canine Kidney (MDCK) cells overexpressing P-glycoprotein (P-gp) and closely related multidrug resistance associated protein 1 (MRP1) to probe the interference with efflux mechanisms mediated by P-gp and MRP1, respectively. A number of substituents at C3 and C4 of coumarin nucleus along with differently sized and shaped spacers was enrolled to investigate the effects of focused structural modifications over affinity and selectivity. Linker length and flexibility played a key role in enhancing P-gp affinity as proved by the most potent P-gp modulator (3h, IC50 = 70 nM). A phenyl ring within the spacer (3k, 3l, 3o) and bulkier groups (Br in 3r, Ph in 3u) at coumarin C3 led to derivatives showing nanomolar activity (160 nM 50 350). Molecular docking calculations carried out on a human MDR1 homology model structure contributed to gain insights into the ligands’ binding modes. Some compounds (3d, 3h, 3l, 3r, 3t, 3u) reversed MDR thereby restoring doxorubicin cytotoxicity when co-administered with the drug into MDCK-MDR1 cells.

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.