Benzo[b][1,4]dioxin-2(3H)-one: Properties, Uses & FAQs

Benzo[b][1,4]dioxin-2(3H)-one is a bicyclic heterocyclic lactone featuring a 1,4-dioxin ring fused to a benzene ring with an ester (lactone) functionality, making it a versatile intermediate in organic synthesis and medicinal chemistry research.

IUPAC Name

Benzo[b][1,4]dioxin-2(3H)-one

SKU / Product Code

B709283

Compound Class

Bicyclic heterocyclic lactone (benzodioxinone)

Core Ring System

1,4-Benzodioxin fused with a lactone (ester) group

Primary Applications

Organic synthesis intermediate, medicinal chemistry, heterocyclic chemistry research

Supplier

Aladdin Scientific (B709283)

What Is Benzo[b][1,4]dioxin-2(3H)-one?

Benzo[b][1,4]dioxin-2(3H)-one is a bicyclic organic compound belonging to the benzodioxinone family. Its structure consists of a benzene ring fused with a six-membered 1,4-dioxin ring that contains a lactone (cyclic ester) carbonyl group. This arrangement provides the molecule with a planar, aromatic-adjacent scaffold that is reactive toward nucleophiles at the carbonyl carbon and susceptible to ring-opening under hydrolytic or aminolytic conditions.

Because of its dual ether-oxygen and ester functionality within a rigid bicyclic framework, Benzo[b][1,4]dioxin-2(3H)-one serves as a valuable building block in heterocyclic chemistry. Researchers exploit the lactone ring as a handle for further functionalization, enabling the preparation of catechol derivatives, amides, and other downstream intermediates relevant to pharmaceutical and agrochemical programs.

Purity, Grade, and Specifications

Aladdin Scientific supplies Benzo[b][1,4]dioxin-2(3H)-one under SKU B709283. Researchers and procurement teams should consult the current product page or Certificate of Analysis (CoA) for the confirmed purity grade, analytical method (e.g., HPLC or GC), and lot-specific data, as specifications may be updated between production batches.

When evaluating reagent suitability for sensitive applications such as asymmetric synthesis or biological screening, always request the CoA for the specific lot number to verify identity (NMR, MS), purity, and appearance. If a higher purity grade or custom quantity is required, contact Aladdin Scientific's technical sales team directly.

Handling, Storage, and Safety

As with most reactive lactone-containing reagents, Benzo[b][1,4]dioxin-2(3H)-one should be handled with appropriate personal protective equipment (PPE), including laboratory coat, chemical-resistant gloves, and safety glasses. Work should be conducted in a well-ventilated fume hood to minimize inhalation exposure to dust or vapors.

Storage recommendations typically include keeping the compound in a tightly sealed container at cool, dry conditions away from moisture, strong bases, and strong nucleophiles that could trigger hydrolysis or ring-opening. Consult the product Safety Data Sheet (SDS) available on the Aladdin Scientific website for full hazard classification, first-aid measures, and disposal guidance specific to this compound and jurisdiction.

Research Applications in Organic and Medicinal Chemistry

Benzo[b][1,4]dioxin-2(3H)-one functions primarily as a synthetic intermediate. The lactone moiety is susceptible to aminolysis, generating 2-(2-hydroxyphenoxy)acetamide-type products, which are of interest in the preparation of pharmacologically active scaffolds. The compound also serves as a masked catechol equivalent: ring-opening under basic conditions can regenerate catechol-containing intermediates useful for natural product synthesis and structure-activity relationship (SAR) studies.

The benzo[1,4]dioxin scaffold itself appears in several bioactive natural products and drug candidates, lending additional relevance to Benzo[b][1,4]dioxin-2(3H)-one as a precursor for exploring this privileged heterocyclic framework. Researchers working on enzyme inhibitors, antimicrobial agents, or receptor ligands may find this building block useful for library synthesis via parallel or combinatorial chemistry approaches.

Ordering and Technical Support

Benzo[b][1,4]dioxin-2(3H)-one is available from Aladdin Scientific under SKU B709283. Orders can be placed through the Aladdin Scientific website, by contacting your regional sales representative, or via approved procurement channels. Volume pricing and bulk quantities may be available upon request.

For technical inquiries regarding purity, compatibility with specific reaction conditions, or custom synthesis requirements, Aladdin Scientific's technical support team is available to assist. Please have your institution's purchase order process and any required safety documentation ready when placing orders for laboratory reagents.

Frequently asked questions

What is the chemical structure of Benzo[b][1,4]dioxin-2(3H)-one?

Benzo[b][1,4]dioxin-2(3H)-one is a bicyclic compound comprising a benzene ring fused to a six-membered 1,4-dioxin ring that incorporates a lactone (cyclic ester) carbonyl group. The two oxygen atoms bridging the benzene and dioxin rings are in a 1,4-arrangement, and the carbonyl at the 2-position constitutes the lactone functionality. This architecture creates a planar, electron-deficient scaffold amenable to nucleophilic ring-opening reactions.

How should Benzo[b][1,4]dioxin-2(3H)-one be stored to maintain stability?

The compound should be stored in a tightly sealed container under cool, dry conditions, away from moisture, strong nucleophiles, and basic reagents that could promote hydrolysis or ring-opening of the lactone. Refer to the Aladdin Scientific Safety Data Sheet (SDS) for lot-specific and jurisdiction-specific storage and handling requirements.

What are the main synthetic uses of Benzo[b][1,4]dioxin-2(3H)-one in research?

This compound is primarily used as a heterocyclic building block in organic and medicinal chemistry. Its lactone group undergoes aminolysis to yield amide-containing catechol-type products, and base-mediated ring-opening can regenerate catechol intermediates for natural product synthesis. The benzo[1,4]dioxin scaffold is also present in various bioactive molecules, making this reagent relevant to SAR studies and library synthesis.

What purity grade is available for B709283 from Aladdin Scientific?

Purity specifications for Benzo[b][1,4]dioxin-2(3H)-one (SKU B709283) should be confirmed by consulting the current product page or requesting the Certificate of Analysis (CoA) for the specific lot, as grades may vary. Contact Aladdin Scientific's sales or technical team for the most up-to-date purity data and to inquire about higher-grade options if required.

Is Benzo[b][1,4]dioxin-2(3H)-one the same as 1,4-benzodioxan-2-one?

Yes, Benzo[b][1,4]dioxin-2(3H)-one and 1,4-benzodioxan-2-one refer to the same core bicyclic lactone structure; the former is the preferred IUPAC systematic name while the latter is a common alternative name used in older literature. Researchers should verify the exact structure via the CAS number or molecular formula when sourcing from catalogs to avoid confusion with related analogs.

References

1. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (General reference for lactone chemistry and bicyclic heterocycles.)
2. Aladdin Scientific. Product Page: Benzo[b][1,4]dioxin-2(3H)-one, SKU B709283. Aladdin Scientific website (accessed 2024).

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