1,2-Cyclohexanedicarboximide: Properties, Handling & Lab Use

1,2-Cyclohexanedicarboximide is a saturated bicyclic imide that serves as a versatile building block and protecting-group precursor in organic synthesis, valued for its defined ring geometry and reactive N–H functionality.

CAS Number

3pa — not disclosed in source; see SDS for confirmed value

Molecular Formula

C8H11NO2

Molecular Weight

Approximately 153.18 g/mol (review flag: confirm from SDS)

Key Functional Group

Cyclic imide (N–H), two carbonyl groups

Physical Form

Solid (review flag: confirm appearance and melting point from SDS)

Solubility

Soluble in polar organic solvents (e.g., DMF, DMSO, ethanol); limited water solubility (review flag: confirm exact values)

Storage Condition

Store at room temperature in a cool, dry place, away from moisture and incompatible materials (review flag: confirm from SDS)

Chemical Identity and Structure

1,2-Cyclohexanedicarboximide (Aladdin SKU: C299265) is derived from 1,2-cyclohexanedicarboxylic acid (hexahydrophthalic acid) by cyclodehydration with ammonia or an amine source to form a five-membered imide ring fused to a six-membered cyclohexane ring. The compound belongs to the class of cyclic imides, characterized by two carbonyl groups flanking a nitrogen atom within a closed ring system. Unlike its aromatic analogue phthalimide, the saturated cyclohexane backbone confers greater conformational flexibility and distinct electronic properties, making it a useful scaffold in medicinal chemistry and total synthesis.

The N–H proton of the imide is moderately acidic (pKa typically in the range observed for cyclic imides; review flag: exact pKa not provided in source material), enabling N-alkylation and N-acylation reactions under mild base conditions. The two carbonyl groups can participate in condensation and reduction reactions, broadening the synthetic utility of this building block.

Physicochemical Properties and Purity Specifications

As a solid cyclic imide, 1,2-Cyclohexanedicarboximide possesses a well-defined melting point that can serve as an identity and purity check (review flag: exact melting point not provided in source; verify from certificate of analysis or SDS). Its molecular formula is C8H11NO2 with a nominal molecular weight of approximately 153.18 g/mol.

Solubility is favored in polar aprotic solvents such as dimethylformamide (DMF) and dimethyl sulfoxide (DMSO), as well as in protic solvents such as ethanol and methanol. Aqueous solubility is limited and pH-dependent due to the weakly acidic N–H group. Researchers should verify lot-specific purity data from the certificate of analysis (CoA) provided with each shipment from Aladdin Scientific. Standard analytical methods for purity assessment include HPLC, NMR spectroscopy, and melting-point determination.

Note: Specific numerical purity grades and lot-specific data are available on the Aladdin Scientific product page for SKU C299265. Always consult the CoA before use in quantitative or biological assays.

Synthetic Applications and Research Uses

1,2-Cyclohexanedicarboximide is employed in organic synthesis primarily as a nitrogen-containing building block and as a precursor for the Gabriel synthesis analogue, where the imide nitrogen is alkylated and subsequently hydrolyzed or hydrazinolyzed to release primary amines. The saturated ring system is advantageous when researchers require sp3-rich, non-planar scaffolds to improve the drug-likeness or three-dimensional diversity of compound libraries.

Additional applications include:

• N-Substituted imide synthesis: Reaction with alkyl halides or Michael acceptors under basic conditions to produce N-alkyl derivatives.
• Chiral auxiliary precursors: The cyclohexane ring can bear substituents that induce asymmetric induction in subsequent transformations (review flag: specific chiral applications not confirmed in source material).
• Polymer chemistry: Cyclic imide monomers are used in the preparation of polyimide materials with defined thermal and mechanical properties.
• Pharmaceutical intermediates: Cyclic imide motifs appear in bioactive molecules; this saturated variant may serve as a bioisostere for planar imide-containing drugs (review flag: specific pharmaceutical citations not provided in source).

Researchers are encouraged to consult primary literature for reaction optimization conditions appropriate to their specific synthetic targets.

Safe Handling, Storage, and Waste Disposal

General Precautions: As with all fine chemical reagents, 1,2-Cyclohexanedicarboximide should be handled using standard laboratory personal protective equipment (PPE), including chemical-resistant gloves, safety spectacles, and a laboratory coat. Operations that generate dust or aerosols should be conducted in a fume hood.

Storage: Store in a tightly sealed container in a cool, dry, well-ventilated location away from moisture, oxidizing agents, and strong bases. The recommended storage temperature should be confirmed against the current SDS and CoA (review flag: exact temperature range not stated in source material).

Stability: Cyclic imides are generally stable under ambient conditions when properly stored. Avoid prolonged exposure to moisture, which may promote hydrolysis of the imide ring over extended periods.

Waste Disposal: Dispose of all waste materials in accordance with local, regional, and national environmental regulations. Do not dispose of down the drain without checking applicable regulations. Contact your institutional environmental health and safety (EHS) office for approved disposal procedures.

Emergency: Consult the Safety Data Sheet (SDS) for first-aid measures, fire-fighting procedures, and spill-response protocols before working with this compound. The SDS for C299265 is available on the Aladdin Scientific website.

Ordering and Quality Assurance at Aladdin Scientific

1,2-Cyclohexanedicarboximide is available from Aladdin Scientific under SKU C299265. Each lot is supplied with a Certificate of Analysis confirming identity, purity, and key physicochemical data. Researchers and procurement personnel can place orders directly through the Aladdin Scientific website or by contacting the sales team.

Quality Commitment: Aladdin Scientific applies rigorous quality control procedures to ensure that reagents meet the stated specifications. Lot-specific CoAs are available for download on the product page. For technical inquiries regarding application suitability, analytical data, or custom packaging options, please contact Aladdin Scientific technical support.

Returns and Compliance: All purchases are subject to Aladdin Scientific's standard terms and conditions. For information on returns, shipping, and payment options, refer to the customer service section of the Aladdin Scientific website.

Frequently asked questions

What is 1,2-Cyclohexanedicarboximide used for in organic synthesis?

It is primarily used as a nitrogen-containing building block for N-alkylation reactions, as a precursor in Gabriel-type amine synthesis, and as a scaffold for preparing sp3-rich heterocyclic intermediates in medicinal chemistry and polymer research.

How should 1,2-Cyclohexanedicarboximide be stored to maintain stability?

Store the compound in a tightly sealed container in a cool, dry, well-ventilated area, away from moisture, oxidizing agents, and strong bases. Prolonged exposure to moisture should be avoided as it can promote hydrolysis of the imide ring. Always refer to the current SDS for confirmed storage conditions.

How does 1,2-Cyclohexanedicarboximide differ from phthalimide?

Unlike phthalimide, which has an aromatic benzene ring fused to the imide ring, 1,2-Cyclohexanedicarboximide contains a saturated cyclohexane ring. This gives the compound greater conformational flexibility, reduced planarity, and different electronic properties, making it preferable in applications where sp3-rich, three-dimensional scaffolds are desired.

Where can I obtain a Certificate of Analysis (CoA) for SKU C299265?

The lot-specific Certificate of Analysis for C299265 is available for download on the Aladdin Scientific product page. You can search by SKU or lot number. For additional assistance, contact Aladdin Scientific customer service.

What solvents are suitable for dissolving 1,2-Cyclohexanedicarboximide?

The compound is generally soluble in polar organic solvents such as DMF, DMSO, ethanol, and methanol. Aqueous solubility is limited and pH-dependent. Exact solubility data should be verified from the SDS or CoA, as source material does not provide specific numerical values.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. General reference for imide chemistry and Gabriel synthesis.
2. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry. Oxford University Press. Reference for cyclic imide reactivity and N-alkylation.
3. Aladdin Scientific. Product Page: 1,2-Cyclohexanedicarboximide, SKU C299265. Certificate of Analysis and Safety Data Sheet. [Online resource]

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