15832-09-4

Basic information

• Product Name: 6-Methoxy-3(2H)-benzofuranone
• Synonyms: 6-Methoxy-3(2H)-benzofuranone;5-Fluoro-3-Benzofuranone;6-Methoxybenzofuran-3(2H)-one;6-Methoxy-3(2H)
• CAS NO: 15832-09-4
• Molecular Formula: C₉H₈O₃
• Molecular Weight: 164.15802
• Mol File: 15832-09-4.mol
• Article Data: 25

Chemical Properties

• Melting Point: 119-120 °C(Solv: ethanol (64-17-5))
• Boiling Point: 313 °C at 760 mmHg
• Flash Point: 134.1 °C
• Appearance: /
• Density: 1.262 g/cm₃
• Vapor Pressure: 0.0114mmHg at 25°C
• Refractive Index: 1.557
• CAS DataBase Reference: 6-Methoxy-3(2H)-benzofuranone(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Methoxy-3(2H)-benzofuranone(15832-09-4)
• EPA Substance Registry System: 6-Methoxy-3(2H)-benzofuranone(15832-09-4)

Safety Data

• Hazardous Substances Data: 15832-09-4(Hazardous Substances Data)

Usage

General Description

6-Methoxy-3(2H)-benzofuranone, also known as eugenol, is an organic compound with a molecular formula C10H12O2. It is a pale yellow, oily liquid with a strong, pleasant clove-like odor. This chemical is commonly found in essential oils such as clove oil, nutmeg, and cinnamon. It has a wide range of applications including use as a flavoring agent in food and beverages, as a fragrance in cosmetic and personal care products, as well as in traditional medicine for its antiseptic and analgesic properties. Additionally, eugenol has been studied for its potential as an antifungal, antibacterial, and antioxidant agent. Due to its versatility, eugenol is a widely used chemical in various industries.

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

Upstream product

• 150-19-6 O-methylresorcine 
• 107-16-4 glycolonitrile 
• 78-97-7 2-hydroxy-propionitrile 
• 4940-44-7 2'-hydroxy-2,4'-dimethoxyacetophenone 
• 10035-10-6 hydrogen bromide 
• 415714-37-3 3-acetoxy-6-methoxy-benzofuran 
• 6272-26-0 6-hydroxybenzofuran-3-one 
• 33562-12-8 methyl 4-methoxy-2-(2-methoxy-2-oxoethoxy)benzoate 
• 5446-02-6 4-methoxymethylsalicylate 
• 755722-84-0 imine 
• 25015-92-3 2-chloro-1-(2,4-dihydroxyphenyl)ethanone 
• 552-41-0 1-(2-hydroxy-4-methoxyphenyl)ethanone 
• 2491-39-6 2-bromo-2',4'-dihydroxyoacetophenone 
• 108-46-3 recorcinol 

Downstream Products

• 94541-27-2 2-((Z)-2-hydroxy-4-methoxy-benzylidene)-6-methoxy-benzofuran-3-one 
• 93876-46-1 2-((Z)-2-hydroxy-4,6-dimethoxy-benzylidene)-6-methoxy-benzofuran-3-one 
• 4940-52-7 2-Benzylidene-6-methoxy-3(2H)-benzofuranone 
• 71005-54-4 (Z)-2-(2-hydroxybenzylidene)-6-methoxybenzofuran-3(2H)-one 
• 32396-82-0 6-methoxy-2-((Z)-vanillylidene)-benzofuran-3-one 
• 36685-46-8 (Z)-2-(3,4-dimethoxybenzylidene)-6-methoxybenzofuran-3(2H)-one 
• 32396-78-4 (Z)-2-(3,4-dihydroxybenzylidene)-6-methoxybenzofuran-3(2H)-one 
• 32396-77-3 (Z)-2-(2,4-dihydroxybenzylidene)-6-methoxybenzofuran-3(2H)-one 
• 132835-41-7 6-methoxy-2,2-diphenylbenzofuran-3(2H)-one 
• 108197-50-8 2-(p-methylbenzylidene)-6-methoxycoumaran-3-one 
• 108197-52-0 2-(p-nitrobenzylidene)-6-methoxycoumaran-3-one 
• 132835-40-6 6-methoxy-2-(2,4,6-trimethoxyphenyl)benzofuran-3(2H)-one 
• 108197-53-1 2-(o-methoxybenzylidene)-6-methoxycoumaran-3-one 
• 108197-51-9 2-(p-bromobenzylidene)-6-methoxycoumaran-3-one 

Relevant articles and documents

Synthesis of novel pyrazole derivatives and their tumor cell growth inhibitory activity

To find novel antitumor agents, a series of 1H-benzofuro[3,2-c]pyrazole derivatives 4a-e were designed and synthesized. The treatment of 6-methoxybenzofuran-3(2H)-one 3 with LiHMDS in anhydrous tetrahydrofuran (THF) followed by reaction with 3-substitued phenyl isothiocyanate gave the thioamide intermediates, which underwent condensation with hydrazine monohydrate in dioxane/EtOH (1:1) to provide the benzofuropyrazole derivatives 4a–e as well as the unexpected pyrazole derivatives 5a–e. In tumor cell growth inhibitory assay, all the benzofuropyrazole derivatives were not active against the breast tumor MCF-7 cell, only 4a was highly active and more potent than ABT-751 against the leukemia K562 (GI50 = 0.26 μM) and lung tumor A549 cells (GI50 = 0.19 μM), while other benzofuropyrazoles showed very weak inhibitory activity. In contrast, the pyrazoles 5a-e were in general more potent than the benzofuropyrazoles 4a–e. Compound 5a exhibited a similar tendency to that of 4a with high potency against K562 and A549 cells but weak effects on MCF-7 cell. Both pyrazoles 5b and 5e exhibited high inhibitory activities against K562, MCF-7 and A549 cells. The most active compound 5b was much more potent than ABT-751 against K562 and A549 cells with GI50 values of 0.021 and 0.69 M, respectively. Moreover, 5b was identified as a novel tubulin polymerization inhibitor with an IC50 of 7.30 M.

Total synthesis of (?)-4-desacetoxy-1-oxovindoline: Single atom exchange of an embedded core heteroatom in vindoline

A concise total synthesis of (?)-4-desacetoxy-1-oxovindoline is disclosed, bearing a single heteroatom exchange in the core structure of the natural product 4-desacetoxyvindoline. Central to the synthesis is powerful oxadiazole intramolecular [4 + 2]/[3 +

A Palladium-Catalyzed Oxa-(4+4)-Cycloaddition Strategy towards Oxazocine Scaffolds

A Pd-catalyzed oxa-(4+4)-cycloaddition between 1-azadienes and (2-hydroxymethyl)allyl carbonates is described. Aurone-derived azadienes furnished polycyclic 1,5-oxazocines in good yields. Interestingly, linear azadienes have also been involved and yielded monocyclic heterocycles with complete regioselectivity. DFT calculations were carried out to gain insight on this observation.