What Is 6-Cyclohexyl-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile?

6-Cyclohexyl-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile (Aladdin SKU: C699963) belongs to the dihydropyrimidinethione (DHPM) family of heterocyclic compounds. The core six-membered ring contains two nitrogen atoms and carries a thioxo group at C-2, an oxo group at C-4, a cyano group at C-5, and a cyclohexyl substituent at C-6.

DHPM scaffolds are well recognised in medicinal chemistry for their structural similarity to the calcium channel blocker nifedipine and related dihydropyridines, and the thio variant of this scaffold has been explored in numerous bioactivity studies. The C-5 nitrile group adds electrophilicity and serves as a handle for further chemical transformations, including conversion to amidines, tetrazoles, or aminopyrimidines.

Physical and Chemical Properties

The compound is a solid at room temperature. The dihydropyrimidinethione ring system is planar around the C2=S and C4=O bonds, and the cyclohexyl group at C-6 introduces steric bulk that influences packing and solubility. Key physicochemical considerations include:

• Molecular formula: C₁₁H₁₅N₃OS
• Molecular weight: 237.32 g/mol (calculated; verify against CoA)
• Appearance: Typically a pale yellow to off-white crystalline powder
• Solubility: Moderately soluble in polar aprotic solvents such as DMSO and DMF; sparingly soluble in water
• Stability: Stable under standard laboratory conditions when stored away from moisture, heat, and strong oxidising agents

Exact melting point, purity, and spectral data (NMR, HRMS) are provided on the product Certificate of Analysis (CoA) available from Aladdin Scientific.

Synthesis and Typical Applications

Synthesis: The Biginelli multicomponent reaction (MCR) is the classic route to DHPM scaffolds. For this compound, a one-pot acid- or Lewis acid-catalysed condensation of cyclohexanecarbaldehyde, a cyanoacetyl equivalent (e.g., malononitrile or ethyl cyanoacetate derivatives), and thiourea typically affords the 2-thioxo-DHPM-5-carbonitrile skeleton. Variations using microwave activation or organocatalysis are reported in the literature.

Applications:

• Medicinal chemistry: The DHPM-thione scaffold with a nitrile at C-5 is a privileged structure explored for anticancer, antimicrobial, and enzyme-inhibitory properties.
• Further functionalisation: The C-5 nitrile can be hydrolysed to an amide or carboxylic acid, cyclised to form fused heterocycles, or converted to an aminopyrimidine via reaction with amines. The C-2 thioxo group is amenable to S-alkylation and S-arylation, enabling library synthesis.
• Coordination chemistry: The thione sulfur and ring nitrogen atoms provide donor sites for metal coordination, making the scaffold of interest in bioinorganic chemistry.

Handling, Storage, and Safety

Handling: Work in a well-ventilated fume hood. Wear appropriate personal protective equipment (PPE) including nitrile gloves, lab coat, and safety glasses. Avoid inhalation of dust and contact with skin or eyes.

Storage: Store in a tightly sealed container in a cool, dry place away from direct sunlight, moisture, and incompatible materials (strong oxidisers, strong bases). Typical recommended storage temperature is 2–8 °C or room temperature in a desiccated environment — refer to the product label and CoA for the confirmed condition.

Disposal: Dispose of in accordance with local regulations for organic sulfur- and nitrogen-containing laboratory waste. Do not pour down the drain.

Note: A full Safety Data Sheet (SDS) is available on the Aladdin Scientific website for C699963. Always consult the SDS before use.

Ordering and Quality Information

6-Cyclohexyl-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile is available from Aladdin Scientific under catalog number C699963. Each lot is accompanied by a Certificate of Analysis (CoA) specifying purity, appearance, molecular weight confirmation, and relevant spectral data.

For bulk quantities, custom synthesis inquiries, or questions about specific purity grades, please contact Aladdin Scientific's technical support or sales team. For reagent specifications and grades, refer to the product page or request the CoA directly.

Orders can be placed through the Aladdin Scientific website, by email, or via authorised distributors. Information on shipping conditions, payment options, and return policies is available in the Help and Customer Service section of the website.