4139-61-1

Basic information

• Product Name: 6-BROMO-4-HYDROXYCOUMARIN
• Synonyms: 6-BROMO-4-HYDROXYCOUMARIN;6-BROMO-4-HYDROXY-2H-CHROMEN-2-ONE;2H-1-Benzopyran-2-one, 6-broMo-4-hydroxy-
• CAS NO: 4139-61-1
• Molecular Formula: C₉H₅BrO₃
• Molecular Weight: 241.04
• Product Categories: Heterocycles series
• Mol File: 4139-61-1.mol
• Article Data: 17

Chemical Properties

• Melting Point: 298°C (dec.)
• Boiling Point: 405.8°Cat760mmHg
• Flash Point: 199.2°C
• Appearance: /
• Density: 1.879g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.69
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 4.50±1.00(Predicted)
• CAS DataBase Reference: 6-BROMO-4-HYDROXYCOUMARIN(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-4-HYDROXYCOUMARIN(4139-61-1)
• EPA Substance Registry System: 6-BROMO-4-HYDROXYCOUMARIN(4139-61-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 20/21/22-22
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 4139-61-1(Hazardous Substances Data)

Usage

General Description

6-Bromo-4-hydroxycoumarin, also known as 6-Bromo-4-coumarinol, is a chemical compound with the molecular formula C9H5BrO3. It is a derivative of coumarin, a natural compound found in many plants. 6-Bromo-4-hydroxycoumarin is commonly used as a reagent in organic synthesis and in the preparation of fluorescent probes for biological imaging. It has also been investigated for its potential pharmacological properties, including its ability to inhibit the growth of cancer cells and its anti-inflammatory effects. Additionally, 6-Bromo-4-hydroxycoumarin has been used in the production of dyes and as an intermediate in the synthesis of pharmaceuticals. Overall, this compound has diverse applications in various scientific and industrial fields due to its unique chemical structure and potential biological activities.

InChI:InChI=1/C9H5BrO3/c10-5-1-2-8-6(3-5)7(11)4-9(12)13-8/h1-4,11H

Upstream product

• 7446-70-0 aluminium trichloride 
• 116210-64-1 bis(4-bromophenyl) malonate 
• 1450-75-5 5-Bromo-2-hydroxyacetophenone 
• 105-58-8 Diethyl carbonate 
• 106-41-2 4-bromo-phenol 
• 1927-95-3 4-bromophenyl acetate 
• 141-82-2 malonic acid 

Downstream Products

• 4699-06-3 6-bromo-3-[4-(3-methyl-4-phenyl-3H-thiazol-2-ylidene)-but-2-enylidene]-chroman-2,4-dione 
• 4699-05-2 6-bromo-3-[2-(3-methyl-4-phenyl-3H-thiazol-2-ylidene)-ethylidene]-chroman-2,4-dione 
• 107638-86-8 6-bromo-4-hydroxy-3-(3-oxo-1-phenylbutyl)chromen-2-one 
• 1262056-70-1 C₂₀H₁₇BrO₅ 
• 1309855-04-6 C₃₆H₂₃BrO₂ 
• 1316832-95-7 C₁₅H₁₃BrO₄ 
• 1316832-31-1 C₁₅H₁₃BrO₄ 
• 1380599-63-2 6-bromo-4-(4-methoxyphenyl)-2H-chromen-2-one 
• 1380599-71-2 C₂₂H₁₅ClO₃ 
• 1380599-72-3 C₂₄H₂₀O₃ 
• 1380599-73-4 C₂₂H₁₅ClO₃ 
• 1380599-74-5 C₂₁H₁₂ClFO₂ 
• 1380599-57-4 C₂₃H₁₈O₄ 
• 1380599-58-5 4,6-bis(4-ethylphenyl)-2H-chromen-2-one 

Relevant articles and documents

TRICYCLIC COMPOUNDS ACTING ON CRBN PROTEINS

The present invention discloses a series of tricyclic compounds and use thereof in preparing a medicament for treating a disease related to CRBN protein. Specifically, the present invention discloses a derivative compound of formula (1) or a pharmaceutically acceptable salt thereof.

Synthesis and anti-inflammatory activity of 2-oxo-2H-chromenyl and 2H-chromenyl-5-oxo-2,5-dihydrofuran-3-carboxylates

Cycloaddition reaction of 4-chloro-2-oxo-2H-chromene-3-carbaldehydes (3a-g) and 4-chloro-2H-chromene-3-carbaldehydes (7a-h) with activated alkynes (4a-b) provided the 2-oxo-2H-chromenyl-5-oxo-2,5-dihydrofuran-3-carboxylates (5a-n) and 2H-chromenyl-5-oxo-2,5-dihydrofuran-3-carboxylates (8a-p). All the prepared compounds were screened for anti-inflammatory activity. In vitro anti-inflammatory activity data demonstrated that the compounds 5g, 5i, 5k-l and 8f are effective among the tested compounds against TNF-α (1.108 ± 0.002, 0.423 ± 0.022, 0.047 ± 0.001, 0.070 ± 0.002 and 0.142 ± 0.001 μM) in comparison with standard compound Prednisolone (0.033 ± 0.002 μM). Based on in vitro results, three compounds (5i, 5k and 8f) have been selected for in vivo experiments and these compounds are identified as better compounds with respect to anti-inflammatory activity in LPS induced mice model. Compound 5i was identified as potent and showed significant reduction in TNF-α and IL-6.

Synthesis of substituted 4-(4-((3-Nitro-2-oxo-2H-chromene-4-yl)amino)phenyl)morpholine-3-one coumarin derivatives

A series of novel 4-(4-amino phenyl) morpholine-3-one substituted coumarin derivatives have been prepared by chloramine coupling reaction and were identified. The novel synthetic route involves nucleophilic substitution reaction of 4-chloro-3-nitro-2H-chromene-2- one with 4-(4-amino phenyl)morpholine-3-one. Due to the presence of nitro group in coumarin derivatives make substitution reaction easy and convenient at low temperature. Using DMF as solvent and K2CO3 as base various substituted 4-(4-((3-nitro-2-oxo-2H-chromen- 4-yl)amino)phenyl)morpholine-3-one derivatives (YS-1 to YS-10) can be obtain in good yield and high purity. Structural characterization of all synthesized compound was done by NMR, Mass and IR spectra.