7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylic Acid: Key FAQs
7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylic Acid: Key FAQs
7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid is a bridged bicyclic compound featuring an oxygen-bridged norbornane skeleton bearing two carboxylic acid functional groups, making it a versatile building block in organic synthesis and materials research.
- Chemical Name
- 7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid
- SKU / Catalog Number
- O664161
- Core Scaffold
- Oxygen-bridged bicyclic (oxanorbornane) ring system
- Key Functional Groups
- Two carboxylic acids (-COOH) at the 2- and 3-positions
- Primary Use
- Synthetic intermediate and building block in organic and medicinal chemistry
- Supplier
- Aladdin Scientific (SKU O664161)
What Is 7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylic Acid?
7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid belongs to the oxanorbornane family of bridged bicyclic compounds. Its ring system consists of a six-membered carbocyclic framework bridged by an oxygen atom at the 7-position, producing the characteristic [2.2.1] bicyclic architecture. Two carboxylic acid groups are located at the 2- and 3-positions of the ring, providing handles for further functionalization via esterification, amidation, or reduction reactions.
The rigid, three-dimensional scaffold of this compound makes it particularly attractive as a building block where defined stereochemistry and conformational constraint are required. The oxygen bridge introduces additional reactivity compared with the all-carbon norbornane analogue, enabling ring-opening chemistry under appropriate conditions.
Handling, Storage, and Safety
As with most carboxylic acid-containing research reagents, 7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid should be handled with standard laboratory precautions. Wear appropriate personal protective equipment including gloves, safety glasses, and a lab coat when weighing or handling this material.
Store the compound in a cool, dry, and well-ventilated location, protected from moisture and incompatible materials such as strong bases and oxidizers. Keep the container tightly sealed when not in use. Consult the product Safety Data Sheet (SDS) available from Aladdin Scientific for detailed hazard classification, first-aid measures, and disposal guidelines specific to this material.
Applications in Organic Synthesis and Research
7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid serves as a versatile bifunctional building block in synthetic organic chemistry. The two carboxylic acid groups can be independently or simultaneously transformed into esters, amides, anhydrides, or reduced to alcohols and aldehydes, enabling access to a broad library of oxanorbornane-derived compounds.
The strained bicyclic framework undergoes retro-Diels-Alder reactions at elevated temperatures, releasing furan and a reactive dienophile — a property exploited in the synthesis of complex natural products and in polymer chemistry for thermally reversible crosslinking systems. The compound is also of interest as a chiral scaffold precursor when enantiomerically enriched forms are employed.
Ordering and Product Specifications
7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid is available from Aladdin Scientific under catalog number O664161. Researchers and procurement teams can place orders directly through the Aladdin Scientific website or by contacting the sales team.
For detailed product specifications — including purity grade, available pack sizes, certificate of analysis (CoA), and current pricing — please visit the product page on the Aladdin Scientific website or contact customer service. Bulk quantities and custom packaging may be available upon request. All products are subject to Aladdin Scientific's standard terms and conditions of sale.
Frequently asked questions
What is the molecular structure of 7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid?
The compound features a bridged bicyclic ring system derived from the norbornane skeleton, in which the C-7 bridge is replaced by an oxygen atom. Two carboxylic acid (-COOH) groups are attached at the 2- and 3-positions of the bicyclic framework, giving the molecule both rigidity and bifunctional reactivity.
What are the main synthetic applications of this compound?
This compound is primarily used as a bifunctional building block in organic synthesis. Its carboxylic acid groups can be converted to esters, amides, or anhydrides, while the strained oxabicyclic ring can undergo retro-Diels-Alder fragmentation at elevated temperatures to generate furan and a reactive dienophile. These properties make it useful in natural product synthesis, medicinal chemistry, and thermally reversible polymer crosslinking.
How should 7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid be stored?
The compound should be stored in a cool, dry, and well-ventilated area, in a tightly sealed container, away from moisture, strong bases, and oxidizing agents. Always refer to the current Safety Data Sheet (SDS) provided by Aladdin Scientific for specific storage and handling requirements.
What catalog number should I use to order this compound from Aladdin Scientific?
7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid is listed under SKU O664161 on the Aladdin Scientific platform. You can search this catalog number directly on the website or provide it to your sales representative when placing an order.
Is 7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid available as a single enantiomer?
The availability of enantiomerically pure forms depends on the current product offering. Please check the Aladdin Scientific product page for SKU O664161 or contact customer service for the most up-to-date information on stereochemical grades and available forms.
References
- March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. General reference for bicyclic compound chemistry and carboxylic acid transformations.
- Aladdin Scientific product page for 7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid, SKU O664161.
- Diels, O.; Alder, K. Synthesis of cyclic systems via diene addition (retro-Diels-Alder general textbook reference). Justus Liebigs Annalen der Chemie, 1928.
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