23000-33-1

Basic information

• Product Name: 3-(4-METHOXYPHENYL)-2H-CHROMEN-2-ONE
• Synonyms: 3-(4-METHOXYPHENYL)-2H-CHROMEN-2-ONE
• CAS NO: 23000-33-1
• Molecular Formula: C₁₆H₁₂O₃
• Molecular Weight: 252.26
• Mol File: 23000-33-1.mol
• Article Data: 49

Chemical Properties

• Boiling Point: 435.9°Cat760mmHg
• Flash Point: 186.1°C
• Appearance: /
• Density: 1.24g/cm³
• Vapor Pressure: 8.42E-08mmHg at 25°C
• Refractive Index: 1.614
• CAS DataBase Reference: 3-(4-METHOXYPHENYL)-2H-CHROMEN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-METHOXYPHENYL)-2H-CHROMEN-2-ONE(23000-33-1)
• EPA Substance Registry System: 3-(4-METHOXYPHENYL)-2H-CHROMEN-2-ONE(23000-33-1)

Safety Data

• Hazardous Substances Data: 23000-33-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H12O3/c1-18-13-8-6-11(7-9-13)14-10-12-4-2-3-5-15(12)19-16(14)17/h2-10H,1H3

Upstream product

• 42945-78-8 2-(4-methoxy-phenyl)-1-morpholin-4-yl-ethanethione 
• 90-02-8 salicylaldehyde 
• 696-62-8 para-iodoanisole 
• 91-64-5 coumarin 
• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 
• 1333483-19-4 N-((4-methoxyphenyl)ethynyl)-N-methylmethanesulfonamide 
• 33675-41-1 1-bromo-2-(4-methoxyphenyl)acetylene 
• 123331-31-7 1-(1H-imidazol-1-yl)-2-(4-methoxyphenyl)ethan-1-one 
• 939-18-4 3-bromo-2H-chromen-2-one 
• 5720-07-0 4-methoxyphenylboronic acid 
• 202391-34-2 2-{2-[(Z)-3,3-Diethoxy-2-(4-methoxy-phenyl)-propenyl]-phenoxy}-tetrahydro-pyran 
• 202391-37-5 3-(p-methoxyphenyl)-3-chromen-2-ol 
• 160559-13-7 ethyl 3-(2-hydroxyphenyl)propiolate 
• 201230-82-2 carbon monoxide 

Downstream Products

• 60678-59-3 3-(2-hydroxy-4-methoxyphenyl)-2H-chromen-2-one 
• 51924-83-5 (E)-1-(2-hydroxyphenyl)-2-(4-methoxyphenyl)-ethene 
• 27247-02-5 3-(4-methoxyphenyl)hydrocoumarin 
• 1404301-84-3 (S)-3-(4-methoxyphenyl)spiro[chroman-2,2'-[1,3]dithiane] 
• 19234-04-9 2-(p-methoxyphenyl)-benzo[b]furan 
• 13130-21-7 3-(2-hydroxyphenyl)-2H-chromen-2-one 

Relevant articles and documents

Dual Role of Oxoaldehydes: Divergent Synthesis of 3-Aryl- and 3-Aroylcoumarins

A facile and efficient synthetic approach to various valuable 3-aryl- and 3-aroylcoumarins by the direct arylation and aroylation of coumarins with glyoxals in a metal-free manner is presented. The aryl glyoxal is for the first time recognized to serve as an aryl surrogate in addition to its role as an aroyl transfer reagent via a simple switch in reaction conditions. The approach accommodates a broad substrate scope and high yields of the two types of cross-coupling reactions starting from identical starting materials.

Chlorophyll-catalyzed photochemical regioselective coumarin C-H arylation with diazonium salts

This communication describes the development of a mild method for the cross-coupling of the C3-position of coumarin with an array of diazonium salts mediated by chlorophyll as a biocatalyst via visible light catalysis. A natural pigment such as chlorophyll is used as a green photosensitizer and environmentally benign catalyst. This general and easy procedure provides a transition-metal-free alternative for the formation of 3-aryl coumarin derivatives at room temperature with good to excellent yields. This journal is

Looking for new xanthine oxidase inhibitors: 3-Phenylcoumarins versus 2-phenylbenzofurans

Overproduction of uric acid in the body leads to hyperuricemia, which is also closely related to gout. Uric acid production can be lowered by xanthine oxidase (XO) inhibitors. Inhibition of XO has also been proposed as a mechanism for improving cardiovascular health. Therefore, the search for new efficient XO inhibitors is an interesting topic in drug discovery. 3-Phenylcoumarins and 2-phenylbenzofurans are privileged scaffolds in medicinal chemistry. Their structural similarity makes them interesting molecules for a comparative study. Methoxy and nitro substituents were introduced in both scaffolds. The current study gives some insights into the synthesis and biological activity of these molecules against this important target. For the best compound of the series, the 3-(4-methoxyphenyl)-6-nitrocoumarin (4), the IC50 value, type of inhibition, cytotoxicity on B16F10 cells and ADME theoretical properties, were determined. Docking studies were also performed in order to better understand the interactions of this molecule with the XO binding pocket. This work is a preliminary screening for further design and synthesis of new non-purinergic derivatives as potential compounds involved in the inflammatory suppression, specially related to gout.