4-Methoxybenzofuran-3(2H)-one: Properties, Uses & Lab Guide

4-Methoxybenzofuran-3(2H)-one is a methoxy-substituted benzofuranone heterocycle of interest in organic synthesis, medicinal chemistry research, and as a versatile building block for constructing complex aromatic lactone frameworks.

Chemical Name

4-Methoxybenzofuran-3(2H)-one

SKU

M698549

Compound Class

Benzofuranone (cyclic lactone with benzofuran scaffold)

Key Functional Groups

Methoxy group (–OCH₃), lactone carbonyl (C=O), aromatic ring

Typical Application

Intermediate in organic and medicinal chemistry synthesis

Storage Recommendation

Store in a cool, dry place away from light and moisture

Chemical Identity and Structure

4-Methoxybenzofuran-3(2H)-one belongs to the benzofuranone family of heterocyclic compounds. Its core structure consists of a benzene ring fused to a five-membered lactone ring, with a methoxy substituent at the 4-position of the aromatic system. This substitution pattern modulates the electron density of the aromatic ring and the reactivity of the adjacent carbonyl group, making the compound a useful platform for further chemical elaboration.

The lactone (cyclic ester) functionality in the 3(2H)-one ring is susceptible to nucleophilic attack, ring-opening reactions, and condensation chemistry. The methoxy group at position 4 is an electron-donating substituent that can influence regioselectivity in electrophilic aromatic substitution and related transformations.

Synthesis and Synthetic Utility

Benzofuran-3(2H)-one derivatives are typically accessible through cyclization strategies starting from appropriately substituted phenoxyacetic acid derivatives or ortho-hydroxy aryl carbonyl precursors. The introduction of the methoxy group at the 4-position can be achieved via directed functionalization of the parent benzofuranone or through choice of suitably substituted starting materials prior to ring closure.

As a synthetic intermediate, 4-Methoxybenzofuran-3(2H)-one offers reactive sites at the α-carbon of the lactone (C-2 position) and at the carbonyl carbon, enabling a range of transformations including Knoevenagel condensations, aldol-type reactions, and nucleophilic additions. These features make it a versatile building block for the preparation of more complex heterocyclic architectures relevant to pharmaceutical and agrochemical research.

Laboratory Handling and Safety

When working with 4-Methoxybenzofuran-3(2H)-one in the laboratory, standard precautions for handling fine organic chemicals should be observed. Personal protective equipment including laboratory coat, chemical-resistant gloves, and safety goggles should be worn at all times during handling. Operations involving weighing or dissolution should be conducted in a well-ventilated fume hood to minimise inhalation exposure.

The compound should be stored in a tightly sealed container in a cool, dry location away from direct light and sources of moisture. Incompatibility with strong oxidising agents and strong bases should be considered when planning reactions. For disposal, follow applicable local regulations for organic chemical waste. Consult the Safety Data Sheet (SDS) provided by Aladdin Scientific before use for full hazard and first-aid information.

Applications in Research

4-Methoxybenzofuran-3(2H)-one and its congeners have attracted attention in medicinal chemistry as scaffolds for bioactive molecule design. Benzofuranone-based structures appear in compounds investigated for a range of biological activities, including antimicrobial, anti-inflammatory, and enzyme-inhibitory properties, though specific activity data for this compound should be verified against primary literature.

In material science and dye chemistry contexts, methoxy-substituted benzofuranones can serve as chromophoric precursors or optical probes. Their use in total synthesis as chiral or prochiral intermediates has also been reported in the broader benzofuranone literature. Researchers are encouraged to consult current peer-reviewed literature for the most up-to-date and compound-specific application data.

Frequently asked questions

What is 4-Methoxybenzofuran-3(2H)-one used for in organic synthesis?

4-Methoxybenzofuran-3(2H)-one serves primarily as a reactive intermediate and building block. Its activated lactone carbonyl and acidic α-methylene allow participation in condensation reactions, nucleophilic additions, and ring-functionalization sequences to generate more complex heterocyclic targets.

How should 4-Methoxybenzofuran-3(2H)-one be stored to maintain quality?

The compound should be stored in a tightly closed container under cool, dry, and dark conditions. Exposure to moisture, heat, and strong light should be avoided to prevent degradation or hydrolysis of the lactone ring. Always reseal the container promptly after use.

Is 4-Methoxybenzofuran-3(2H)-one related to any natural products?

The benzofuranone scaffold is found in various naturally occurring compounds and pharmaceutically relevant molecules. However, specific natural product relationships for 4-Methoxybenzofuran-3(2H)-one itself should be confirmed through primary literature, as Aladdin Scientific does not make explicit natural product claims for this reagent.

What purity grade is Aladdin's M698549 supplied at?

Purity and specification details for SKU M698549 are available on the Aladdin Scientific product page. Customers requiring a specific purity grade or analytical certificate should contact Aladdin Scientific technical support or consult the product listing directly.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley, 5th ed. General reference for lactone and heterocycle reactivity.
2. Joule, J. A.; Mills, K. Heterocyclic Chemistry. Blackwell Science, 5th ed. General reference for benzofuranone chemistry.
3. Aladdin Scientific product listing for 4-Methoxybenzofuran-3(2H)-one, SKU M698549.

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.