Chemical Identity and Structure

tert-Butyl 2,5-dihydrofuran-3-carboxylate (SKU: T768785; also referenced as B955073 in partner catalogs) belongs to the class of partially unsaturated oxygen heterocycles. Its core is a 2,5-dihydrofuran ring—a five-membered ring containing one oxygen atom and one endocyclic double bond between C3 and C4—decorated at C3 with a tert-butyl ester group.

The molecular formula is C₉H₁₄O₃, giving a molecular weight of approximately 170.21 g/mol. The compound combines two orthogonal reactive sites: (1) the electron-rich enol ether alkene, susceptible to electrophilic addition, cycloaddition, and oxidative functionalization; and (2) the acid-labile tert-butyl ester, readily cleaved under mild acidic conditions (e.g., trifluoroacetic acid or HCl in dioxane) to reveal the corresponding carboxylic acid without disturbing other sensitive functionality.

This dual reactivity profile distinguishes tert-Butyl 2,5-dihydrofuran-3-carboxylate from fully saturated tetrahydrofuran analogs and from aromatic furan derivatives, positioning it as a uniquely flexible platform for multi-step synthesis.

Synthetic Applications and Reactivity

Enol Ether Reactivity: The 2,5-dihydrofuran ring acts as an electron-rich alkene partner in a range of transformations. It is well-documented that dihydrofurans participate in Diels-Alder reactions as dienophiles when paired with appropriate dienes, and as heterodienes under inverse electron demand conditions. This makes tert-Butyl 2,5-dihydrofuran-3-carboxylate attractive for rapid construction of bicyclic and polycyclic oxygen-containing scaffolds.

Electrophilic Addition: Halogens, halogen equivalents, and other electrophiles can add across the C3–C4 double bond in a stereoselective manner, enabling access to 2,3- or 3,4-functionalized tetrahydrofuran products after ring opening or further manipulation.

tert-Butyl Ester Utility: The tert-butyl ester serves as a masked carboxylic acid, compatible with a wide range of reaction conditions including basic, neutral, and mildly acidic environments. Deprotection is achieved selectively with strong acids under mild temperature conditions, providing the free acid for coupling reactions, further derivatization, or biological evaluation.

Oxidation and Epoxidation: The endocyclic alkene can be epoxidized using standard reagents (e.g., mCPBA), yielding strained epoxide intermediates that undergo regioselective ring-opening to give highly functionalized tetrahydrofuranols—useful fragments in natural product synthesis and drug discovery.

Note: Specific reaction yields, conditions, and stereoselectivity data should be verified against primary literature before use in critical applications.

Handling, Storage, and Safety Guidelines

Personal Protective Equipment (PPE): When handling tert-Butyl 2,5-dihydrofuran-3-carboxylate, wear appropriate laboratory PPE including nitrile gloves, safety goggles, and a lab coat. Work in a well-ventilated fume hood to minimize inhalation of vapors.

Storage Conditions: Store the compound in a tightly sealed container in a cool, dry location away from direct light and moisture. Keep away from strong oxidizing agents and strong acids, which may react with the enol ether or cleave the tert-butyl ester prematurely. Refrigerated storage (2–8 °C) is recommended for long-term stability, though the specific recommended temperature range should be confirmed from the product specification sheet (SDS/TDS).

Stability Considerations: The enol ether functionality renders the compound sensitive to acidic conditions and prolonged exposure to atmospheric moisture. Aliquot and store under inert atmosphere (nitrogen or argon) if extended storage is required. Avoid contact with protic acids to prevent undesired hydrolysis or ester cleavage.

Disposal: Dispose of waste material in accordance with local institutional and governmental regulations for organic chemical waste. Do not dispose of down the drain.

Always consult the current Safety Data Sheet (SDS) for T768785 prior to use. Specific hazard classifications and GHS pictograms should be verified from the official SDS document.

Quality, Specifications, and Procurement

Aladdin Scientific SKU: T768785. This product is also cross-referenced as B955073 in partner supplier catalogs (e.g., Macklin), facilitating cross-platform sourcing verification.

Purity and Grade: Aladdin Scientific supplies research-grade reagents intended for laboratory and R&D applications. Specific purity specifications (e.g., ≥95% or ≥97% by GC or HPLC) should be confirmed directly from the current Certificate of Analysis (CoA) available on the Aladdin Scientific product page or upon request. Lot-specific CoAs provide NMR, purity, and appearance data.

Available Pack Sizes: Contact Aladdin Scientific or visit the product listing for current available quantities. Bulk or custom quantities may be available upon inquiry.

Ordering: tert-Butyl 2,5-dihydrofuran-3-carboxylate (T768785) can be ordered directly through the Aladdin Scientific website or via your institutional procurement system. For volume pricing, framework agreements, or technical pre-sales enquiries, contact the Aladdin Scientific sales team.

Regulatory: This compound is supplied for research use only and is not intended for diagnostic, therapeutic, or food applications.