7169-35-9

Basic information

• Product Name: 4-Methoxy-3(2H)-benzofuranone
• Synonyms: 4-Methoxy-3(2H)-benzofuranone;6-Fluoro-3-Benzofuranone;4-Methoxybenzofuran-3(2H)-one
• CAS NO: 7169-35-9
• Molecular Formula: C₉H₈O₃
• Molecular Weight: 164.15802
• Mol File: 7169-35-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 147-148 °C
• Boiling Point: 314.9 °C at 760 mmHg
• Flash Point: 135.2 °C
• Appearance: /
• Density: 1.262 g/cm³
• Vapor Pressure: 0.0114mmHg at 25°C
• Refractive Index: 1.557
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-Methoxy-3(2H)-benzofuranone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methoxy-3(2H)-benzofuranone(7169-35-9)
• EPA Substance Registry System: 4-Methoxy-3(2H)-benzofuranone(7169-35-9)

Safety Data

• Hazardous Substances Data: 7169-35-9(Hazardous Substances Data)

Usage

General Description

4-Methoxy-3(2H)-benzofuranone, also known as phivolide, is a synthetic chemical compound with a molecular formula C9H8O3. It is a colorless to white solid that is commonly used in the fragrance industry due to its sweet, vanilla-like aroma. 4-Methoxy-3(2H)-benzofuranone is often used as a flavoring agent in food products and as a fragrance in perfumes and personal care products. It is also utilized in the production of pharmaceuticals and in organic synthesis. Additionally, 4-Methoxy-3(2H)-benzofuranone has been studied for its potential anti-inflammatory and antioxidant properties, making it a compound of interest in medicinal research.

InChI:InChI=1/C8H5FO2/c9-5-1-2-6-7(10)4-11-8(6)3-5/h1-3H,4H2

Upstream product

• 135746-09-7 2'-hydroxy-6'-methoxychalcone epoxide 
• 105285-09-4 (E)-1-(2-hydroxy-6-methoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one 

Relevant articles and documents

Synthesis of 5-subsituted flavonols via the Algar-Flynn-Oyamada (AFO) reaction: The mechanistic implication

Herein, we report a synthetic method with improved selectivity for 5-substituted flavonols via the Algar-Flynn-Oyamada reaction (AFO), by using of sodium carbonate/hydrogen peroxide A series of 5-substituted flavonols was obtained with moderate to high yields. The mechanism of the AFO reaction was elucidated. LCMS analysis and in situ 1H NMR analysis indicated that the epoxide was involved in the transformation from chalcone to flavonol and/or aurone under alkaline base/peroxide conditions.

Cyclisation and subsequent reactions of 2′-hydroxy-6′-methoxychalcone epoxide and related compounds

2′-Hydroxy-6′-methoxychalcone epoxide reacts in neutral aqueous acetonitrile solution to give a 6:1 ratio of the α- and β-cyclisation products, erythro-4-methoxyaurone hydrate [erythro-2-(α-hydroxybenzyl)-4-methoxycoumaran-3-one] and trans-3-hydroxy-5-methoxyflavanone: the dominance of α-cyclisation may be associated with a stereoelectronic preference for a conformation favourable for α- but not β-cyclisation when the carbonyl group is forced by the 6′-substituent to lie out-of-plane with the aromatic ring. In more basic solutions, erythro-threo isomerisation of aurone hydrate occurs, and 4-methoxycoumaran-3-one and 4-methoxyaurone are formed. Other 6′-substituted 2′-hydroxychalcone epoxides show a similar strong preference for α- over β-cyclisation.