(-)-trans-1,2-Cyclohexanedicarboxylic Anhydride: FAQs

(-)-trans-1,2-Cyclohexanedicarboxylic Anhydride is a chiral cyclic anhydride serving as a versatile enantiopure building block in asymmetric synthesis, polymer chemistry, and pharmaceutical research.

Chemical Name

(-)-trans-1,2-Cyclohexanedicarboxylic Anhydride

Stereochemistry

Enantiopure trans configuration; single enantiomer

Functional Group

Cyclic carboxylic anhydride

Primary Applications

Asymmetric synthesis, chiral resolution, polymer research, pharmaceutical intermediates

Storage Recommendation

Store in a cool, dry place away from moisture; seal tightly after use

Reactivity

Reacts readily with nucleophiles (amines, alcohols, water); moisture-sensitive

What Is (-)-trans-1,2-Cyclohexanedicarboxylic Anhydride and Why Is It Used?

(-)-trans-1,2-Cyclohexanedicarboxylic Anhydride is a chiral, enantiopure cyclic anhydride derived from the corresponding trans-1,2-cyclohexanedicarboxylic acid. Its rigid trans-fused ring system locks the two carboxyl groups in a specific spatial arrangement, making it a highly valuable chiral building block.

Researchers employ this compound primarily in asymmetric synthesis, where the defined stereocenters can be transferred to target molecules with high enantioselectivity. It is also used as a chiral derivatizing agent for the resolution of racemic amines and alcohols, and as a precursor in the preparation of chiral polyimides and polyamides for materials science applications.

In medicinal chemistry, enantiopure cyclic anhydrides such as this compound serve as intermediates for constructing complex pharmaceutical scaffolds where absolute configuration is critical for biological activity.

Chemical Properties and Handling

As a cyclic anhydride, (-)-trans-1,2-Cyclohexanedicarboxylic Anhydride is electrophilic at the carbonyl carbons and reacts readily with nucleophiles including amines, alcohols, and water. Hydrolysis by atmospheric moisture will convert the anhydride to the corresponding dicarboxylic acid, reducing reagent efficacy over time.

Key handling precautions include: working under anhydrous conditions or in a dry atmosphere (e.g., nitrogen or argon glove box or Schlenk techniques) when moisture-sensitivity is a concern; wearing appropriate personal protective equipment (gloves, lab coat, eye protection) since the compound can be an irritant; and avoiding inhalation of dust or vapors.

The compound should be stored in a tightly sealed container in a cool, dry location. Desiccants such as molecular sieves or silica gel pouches inside the storage container can help maintain anhydrous conditions during long-term storage.

Purity, Quality, and Analytical Specifications

For asymmetric synthesis and chiral applications, the enantiomeric excess (ee) and chemical purity of (-)-trans-1,2-Cyclohexanedicarboxylic Anhydride are critical parameters. Researchers should request a Certificate of Analysis (CoA) from the supplier, which typically reports purity by gas chromatography (GC) or high-performance liquid chromatography (HPLC), as well as the optical rotation value confirming the enantiopurity.

When evaluating a reagent lot, verify that the optical rotation ([α]D) matches the expected value for the (-) enantiomer, and confirm that any stated ee value meets the requirements of your synthetic application. For highly stereoselective transformations, reagents with ≥98% ee are generally preferred.

Aladdin Scientific provides product-specific CoAs and technical data for SKU T161605 to help researchers make informed purchasing decisions.

Ordering, Shipping, and Storage Guidelines

(-)-trans-1,2-Cyclohexanedicarboxylic Anhydride (SKU T161605) is available from Aladdin Scientific. When placing an order, confirm the required quantity and packaging size to match your experimental scale and to minimize waste from repeated opening of containers.

Shipping: Because this reagent is moisture-sensitive, Aladdin Scientific packages it to minimize exposure during transit. Upon receipt, inspect the packaging for damage and store the material immediately under recommended conditions. If the material appears discolored or clumped, contact Aladdin Scientific customer service to discuss a replacement or quality concern.

For long-term storage, keep the original sealed container in a cool (room temperature or below, following CoA guidance), dry environment. Record the date of first opening, as opened containers should be used within a reasonable timeframe and re-sealed promptly after each use to preserve reagent quality.

Frequently asked questions

What is the difference between the (-)-trans and other stereoisomers of 1,2-cyclohexanedicarboxylic anhydride?

The (-)-trans isomer is a single enantiomer with a defined absolute configuration at both stereocenters, giving it a specific optical rotation (negative, levorotatory). The (+)-trans enantiomer is its mirror image and will induce opposite stereocontrol in asymmetric reactions. The cis isomers have different spatial arrangements and distinct reactivity profiles. For applications requiring precise stereocontrol, using the correct enantiopure isomer is essential.

How should I handle (-)-trans-1,2-Cyclohexanedicarboxylic Anhydride to prevent degradation?

To prevent hydrolysis, handle the reagent under dry conditions and minimize exposure to atmospheric moisture. Use dry solvents and glassware, work under inert gas when possible, and reseal the container tightly immediately after use. Store with a desiccant in a cool, dry location. If the reagent has been exposed to moisture, check purity by NMR or HPLC before use to confirm it still meets specifications.

What solvents are compatible with (-)-trans-1,2-Cyclohexanedicarboxylic Anhydride?

This anhydride is generally soluble in common aprotic organic solvents such as dichloromethane, tetrahydrofuran, ethyl acetate, acetonitrile, and toluene. Protic solvents (e.g., methanol, ethanol, water) should be avoided unless deliberate reaction with the anhydride is intended, as they will react with and destroy the anhydride functionality. Always consult the CoA and primary literature for solubility data specific to your application.

Can (-)-trans-1,2-Cyclohexanedicarboxylic Anhydride be used as a chiral derivatizing agent?

Yes, enantiopure cyclic anhydrides are well-established chiral derivatizing agents for the determination of enantiomeric purity of amines and alcohols by NMR or HPLC. By reacting the racemic substrate with this enantiopure anhydride, diastereomeric derivatives are formed that can be distinguished analytically. The specific application protocol should be validated in your laboratory system.

What is the SKU for (-)-trans-1,2-Cyclohexanedicarboxylic Anhydride at Aladdin Scientific?

The SKU for (-)-trans-1,2-Cyclohexanedicarboxylic Anhydride at Aladdin Scientific is T161605. You can use this SKU to quickly locate the product, request a quote, or access the Certificate of Analysis on the Aladdin Scientific website.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. General reference for anhydride reactivity and properties.
2. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds. Wiley. Reference for chiral anhydrides and stereochemical principles.
3. Aladdin Scientific Product Page: (-)-trans-1,2-Cyclohexanedicarboxylic Anhydride, SKU T161605. Aladdin Scientific.

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