3-Acetoxybenzo[b]furan: Properties, Uses & FAQs

3-Acetoxybenzo[b]furan is a benzofuran-derived heterocyclic compound bearing an acetoxy substituent at the 3-position, used as a versatile building block in organic synthesis and medicinal chemistry research.

Chemical Name

3-Acetoxybenzo[b]furan

Aladdin SKU

A700658

Core Scaffold

Benzo[b]furan (bicyclic oxygen-containing heterocycle)

Functional Group

Acetoxy group (–OC(O)CH₃) at the 3-position

Primary Application

Intermediate in organic synthesis and heterocyclic chemistry research

Storage Recommendation

Store in a cool, dry, well-ventilated area away from heat and incompatible materials

What Is 3-Acetoxybenzo[b]furan?

3-Acetoxybenzo[b]furan is a synthetic organic compound belonging to the benzofuran family of heterocycles. Its structure consists of a fused bicyclic system in which a benzene ring is annulated to a furan ring, with an acetoxy (–OC(O)CH₃) group attached at the 3-position of the furan ring. This substitution pattern makes the 3-position electrophilically activated and amenable to a range of further chemical transformations.

The benzo[b]furan scaffold is widely encountered in natural products, pharmaceuticals, and advanced organic intermediates. Introduction of the acetoxy group at C-3 modifies the electronic character of the heterocyclic system and provides a handle for nucleophilic substitution, hydrolysis to the corresponding 3-hydroxybenzofuran, or participation in transition-metal-catalyzed coupling reactions.

Physical and Chemical Properties

3-Acetoxybenzo[b]furan is typically obtained as a solid or low-melting crystalline material. The molecular formula is C₁₀H₈O₃, corresponding to a molecular weight of approximately 176.17 g/mol. The compound contains an ester linkage (the acetoxy group) that is susceptible to hydrolysis under both acidic and basic conditions, generating 3-hydroxybenzo[b]furan and acetic acid.

As an aromatic heterocyclic ester, 3-Acetoxybenzo[b]furan is expected to be sparingly soluble in water but readily soluble in common organic solvents such as dichloromethane, ethyl acetate, acetonitrile, and tetrahydrofuran. The compound should be handled under standard laboratory conditions with appropriate personal protective equipment, as with all reactive organic intermediates.

Research Applications and Synthetic Utility

The primary utility of 3-Acetoxybenzo[b]furan lies in its role as an activated heterocyclic intermediate in organic synthesis. The acetoxy group at C-3 can act as a leaving group in palladium-catalyzed allylic substitution or related cross-coupling reactions, enabling the introduction of diverse nucleophiles to construct more complex benzofuran derivatives.

Benzofuran-containing motifs are of considerable interest in medicinal chemistry owing to their presence in biologically active natural products and drug candidates. Researchers utilize 3-substituted benzofuran building blocks to explore structure–activity relationships in areas including anti-inflammatory, antimicrobial, and antifungal research programs. 3-Acetoxybenzo[b]furan therefore serves as a versatile precursor for library synthesis and lead-optimization campaigns.

Storage, Handling, and Safety

3-Acetoxybenzo[b]furan should be stored in a tightly sealed container in a cool, dry, and well-ventilated location, away from heat sources, open flames, and incompatible reagents such as strong bases or strong acids that could promote hydrolysis of the ester functionality. Moisture exclusion is advisable to maintain product integrity over time.

Standard laboratory personal protective equipment—including chemical-resistant gloves, safety goggles, and a laboratory coat—should be worn when handling this compound. Work in a fume hood is recommended to minimize inhalation exposure. Consult the Safety Data Sheet (SDS) supplied with the product for comprehensive hazard information, first-aid measures, and disposal guidelines before use.

Ordering and Quality Information

3-Acetoxybenzo[b]furan is available from Aladdin Scientific under SKU A700658. Aladdin Scientific supplies research-grade reagents to academic institutions, pharmaceutical companies, and contract research organizations worldwide. Product purity specifications and analytical data (such as NMR or HPLC certificates of analysis) are available upon request or via the product page.

For bulk quantities, custom packaging, or technical inquiries regarding 3-Acetoxybenzo[b]furan, customers are encouraged to contact the Aladdin Scientific sales and technical support team. Orders can be placed through the Aladdin Scientific website or through authorized distributors in your region.

Frequently asked questions

What is the molecular formula and molecular weight of 3-Acetoxybenzo[b]furan?

3-Acetoxybenzo[b]furan has the molecular formula C₁₀H₈O₃ and a molecular weight of approximately 176.17 g/mol. It consists of a benzo[b]furan core with an acetoxy (–OC(O)CH₃) substituent at the 3-position.

What solvents are suitable for dissolving 3-Acetoxybenzo[b]furan?

3-Acetoxybenzo[b]furan is sparingly soluble in water but is expected to dissolve readily in common organic solvents including dichloromethane, ethyl acetate, acetonitrile, and tetrahydrofuran. Avoid prolonged exposure to strongly acidic or basic aqueous media, as these conditions promote hydrolysis of the acetoxy ester group.

How should 3-Acetoxybenzo[b]furan be stored to maintain stability?

Store 3-Acetoxybenzo[b]furan in a tightly sealed container in a cool, dry, well-ventilated area away from heat, ignition sources, moisture, strong acids, and strong bases. Moisture exclusion is particularly important because the acetoxy ester functionality is susceptible to hydrolysis. Always refer to the product SDS for full storage and safety instructions.

What are the main synthetic applications of 3-Acetoxybenzo[b]furan?

3-Acetoxybenzo[b]furan serves primarily as an activated heterocyclic building block in organic synthesis. The acetoxy group at C-3 can function as a leaving group in transition-metal-catalyzed reactions, facilitating the introduction of diverse nucleophiles to produce 3-substituted benzofuran derivatives. These derivatives are of interest in medicinal chemistry and natural-product synthesis.

What is the Aladdin Scientific product SKU for 3-Acetoxybenzo[b]furan?

3-Acetoxybenzo[b]furan is listed under SKU A700658 in the Aladdin Scientific catalog. Customers can order directly through the Aladdin Scientific website or contact the technical sales team for pricing, availability, and bulk quantity inquiries.

References

1. Joule, J. A.; Mills, K. Heterocyclic Chemistry, 5th ed.; Wiley-Blackwell: Oxford, 2010. (General reference for benzofuran chemistry and reactivity.)
2. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (Textbook-level reference for ester hydrolysis and nucleophilic substitution reactions.)
3. Aladdin Scientific product page for 3-Acetoxybenzo[b]furan, SKU A700658. Aladdin Scientific, Shanghai. (Product specification reference.)

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