Ethyl 1-Cyanocyclohexanecarboxylate: Properties & Lab Use Guide

Ethyl 1-cyanocyclohexanecarboxylate is a bifunctional organic intermediate featuring both a nitrile and an ethyl ester group on a quaternary carbon center of a cyclohexane ring, making it a versatile building block in synthetic organic chemistry.

Chemical Name

Ethyl 1-cyanocyclohexanecarboxylate

SKU

E725369

Molecular Formula

C9H13NO2

Key Functional Groups

Nitrile (–CN) and ethyl ester (–CO2Et) on a quaternary carbon

Molecular Weight

167.21 g/mol

Primary Application

Synthetic intermediate for quaternary carbon-containing targets in medicinal and fine chemistry

Chemical Identity and Structure

Ethyl 1-cyanocyclohexanecarboxylate (SKU E725369, molecular formula C₉H₁₃NO₂, MW ~167.21 g/mol) belongs to the class of α-cyano esters. Its defining structural feature is a fully substituted (quaternary) carbon at the 1-position of the cyclohexane ring bearing both a nitrile group (–CN) and an ethyl ester group (–CO₂CH₂CH₃). This dual electron-withdrawing substitution activates the molecule toward a wide range of nucleophilic and condensation reactions. The cyclohexane scaffold imparts conformational rigidity relative to open-chain analogs, which can be advantageous in controlling stereoselectivity and product geometry in downstream transformations.

Synthetic Applications

The compound serves as a valuable building block in multi-step organic synthesis, particularly for constructing quaternary carbon centers that are otherwise challenging to access. Representative applications include:

• Hydrolysis and decarboxylation: The ester group can be selectively hydrolyzed under basic or acidic conditions to yield the corresponding carboxylic acid, followed by decarboxylation to furnish 1-cyanocyclohexane derivatives.
• Nitrile transformation: The –CN group can be reduced (e.g., with LiAlH₄ or catalytic hydrogenation) to the primary amine, hydrolyzed to the amide or carboxylic acid, or employed in cycloaddition reactions to generate heterocyclic scaffolds.
• Knoevenagel and related condensations: The active methylene character activated by the flanking nitrile and ester groups facilitates condensation reactions with aldehydes and ketones.
• Medicinal chemistry intermediates: Quaternary α-amino acid analogs and spirocyclic compounds accessible from this substrate are of interest in drug discovery programs.

Researchers should optimize reaction conditions—solvent, base, temperature—according to the specific transformation planned.

Handling, Storage, and Safety Guidelines

As with all nitrile-containing compounds, appropriate precautions should be observed when handling Ethyl 1-cyanocyclohexanecarboxylate:

• Personal Protective Equipment (PPE): Wear chemically resistant gloves (e.g., nitrile), safety goggles, and a laboratory coat. Work in a well-ventilated fume hood to avoid inhalation of vapors or aerosols.
• Storage: Store in a tightly sealed container in a cool, dry, well-ventilated area away from incompatible materials (strong oxidizers, strong bases, strong acids). Typical storage temperature is 2–25 °C; refer to the product label and Safety Data Sheet (SDS) for confirmed specifications.
• Waste disposal: Dispose of material and contaminated items in accordance with local, regional, and national regulations for organic nitrile-containing waste.
• First aid: In case of skin or eye contact, flush immediately with copious water for at least 15 minutes and seek medical attention. If ingested or inhaled, seek immediate medical attention and provide the SDS to attending medical personnel.

Always consult the product SDS before use. Safety data presented here are general guidelines and do not substitute for the official SDS.

Quality, Purity, and Procurement

Aladdin Scientific supplies Ethyl 1-cyanocyclohexanecarboxylate (SKU E725369) as a research-grade reagent. When evaluating this or any reagent for use in sensitive synthetic workflows, consider the following:

• Purity verification: Confirm purity by NMR, GC, or HPLC analysis prior to use in critical transformations. Request a Certificate of Analysis (CoA) from Aladdin Scientific at the time of purchase.
• Lot-to-lot consistency: For multi-batch projects, specify lot numbers and retain CoA records to ensure reproducibility.
• Packaging and quantity: Available in research quantities suited to laboratory-scale synthesis. Contact Aladdin Scientific for bulk or custom packaging inquiries.
• Regulatory compliance: The compound does not appear on common controlled-substance schedules, but users should verify applicable local import/export and handling regulations.

Frequently asked questions

What is Ethyl 1-cyanocyclohexanecarboxylate used for in organic synthesis?

It is primarily used as a bifunctional building block for constructing quaternary carbon centers. The nitrile and ester groups can be independently transformed via reduction, hydrolysis, or condensation reactions, enabling access to amines, carboxylic acids, heterocycles, and spirocyclic intermediates relevant to medicinal chemistry.

How should Ethyl 1-cyanocyclohexanecarboxylate be stored to maintain stability?

The compound should be stored in a tightly sealed container under cool, dry, and well-ventilated conditions, away from strong oxidizers and bases. A storage temperature of 2–25 °C is generally recommended; always refer to the product label and official SDS for confirmed conditions.

Can the nitrile group in Ethyl 1-cyanocyclohexanecarboxylate be selectively reduced without affecting the ester?

Selective reduction of the nitrile group to a primary amine is possible using mild reducing agents or carefully controlled catalytic hydrogenation conditions, although chemoselectivity can be challenging given the presence of the ester. Reaction conditions should be optimized and tested at small scale; consult the primary literature for validated protocols.

Where can I obtain the Safety Data Sheet (SDS) for Ethyl 1-cyanocyclohexanecarboxylate?

The SDS for SKU E725369 is available through the Aladdin Scientific website on the product page. Procurement teams and lab managers should download and review the SDS before the first use and ensure it is accessible at the point of use in the laboratory.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; Wiley-Interscience: New York, 1992. (General reference for nitrile and ester chemistry.)
2. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (General reference for synthetic transformations of nitrile and ester functional groups.)
3. Aladdin Scientific. Product Page: Ethyl 1-cyanocyclohexanecarboxylate, SKU E725369. (Consult for current purity, pricing, and SDS.)

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