Chemical Identity and Structure

Ethyl 5-(tert-butyl)-1H-pyrazole-3-carboxylate belongs to the pyrazole family of five-membered nitrogen-containing heterocycles. Its structure features a 1H-pyrazole ring bearing a sterically demanding tert-butyl group at the 5-position and an ethyl ester moiety at the 3-position. The free N–H at position 1 enables tautomerism between the 3- and 5-substituted forms (3-carboxylate/5-tert-butyl and 5-carboxylate/3-tert-butyl), a common characteristic of 1H-pyrazoles.

The tert-butyl substituent confers significant steric bulk, which can influence regioselectivity in downstream functionalization reactions and improve metabolic stability when incorporated into drug candidates. The ethyl ester group serves as a versatile handle for further chemical transformations, including hydrolysis to the corresponding carboxylic acid, reduction to the alcohol, conversion to amides, or use in condensation reactions.

Aladdin Scientific supplies this compound under SKU E1369778, providing researchers with a reliable source of this important heterocyclic building block.

Physicochemical Properties and Solubility

As a relatively lipophilic small molecule, Ethyl 5-(tert-butyl)-1H-pyrazole-3-carboxylate is expected to show good solubility in common organic solvents such as dichloromethane (DCM), ethyl acetate, tetrahydrofuran (THF), dimethyl sulfoxide (DMSO), and acetonitrile. Solubility in water is anticipated to be low due to the hydrophobic tert-butyl group and the non-polar ethyl ester, though the pyrazole N–H can participate in hydrogen bonding.

When preparing stock solutions for biological assays, DMSO is the recommended solvent. Researchers should verify the actual solubility empirically at their target concentrations, as solubility can vary with temperature, pH, and the specific solvent system used.

The compound is expected to be a solid at room temperature based on the molecular structure of analogous pyrazole esters. Handling as a solid requires standard laboratory precautions to avoid inhalation of dust.

Note: Specific melting point, boiling point, and density values are not confirmed in the available source material and should be verified from the product Certificate of Analysis (CoA) or peer-reviewed literature before use in critical applications.

Synthetic Applications and Reactivity

Ethyl 5-(tert-butyl)-1H-pyrazole-3-carboxylate serves as a multifunctional intermediate in organic synthesis. Key transformations exploiting its reactive functional groups include:

• N-Alkylation and N-Arylation: The pyrazole N–H can be alkylated or arylated under basic conditions to give N-substituted pyrazoles, enabling access to a wide range of N-functionalized derivatives relevant to medicinal chemistry programs.
• Ester Hydrolysis: Treatment with aqueous base (e.g., NaOH or KOH in ethanol/water) furnishes the corresponding 5-(tert-butyl)-1H-pyrazole-3-carboxylic acid, a useful carboxylic acid building block for amide coupling reactions.
• Amide Bond Formation: Activation of the ethyl ester or the derived carboxylic acid with coupling reagents (e.g., EDC, HATU, DIC) allows efficient preparation of pyrazole carboxamides, a privileged motif in kinase inhibitors and other bioactive compounds.
• Coordination Chemistry: The pyrazole nitrogen atoms and the ester oxygen can act as donor atoms for metal coordination, making this compound a precursor to pyrazole-based ligands used in catalysis and materials science.

The steric influence of the tert-butyl group at C-5 can direct regioselectivity during electrophilic and nucleophilic substitutions on the pyrazole ring, which researchers should account for during reaction design.

Handling, Storage, and Safety Guidelines

Researchers handling Ethyl 5-(tert-butyl)-1H-pyrazole-3-carboxylate should follow standard laboratory safety protocols for organic reagents:

• Personal Protective Equipment (PPE): Wear appropriate chemical-resistant gloves, safety goggles, and a laboratory coat at all times when handling the compound. If generating dust during weighing, use a fume hood or respiratory protection.
• Storage: Store in a tightly sealed container in a cool, dry, well-ventilated area, away from heat sources, open flames, and incompatible materials such as strong oxidizers and strong bases. Recommended storage temperature should be confirmed from the product CoA.
• Stability: Like most pyrazole ester compounds, this reagent should be kept dry to prevent hydrolysis of the ethyl ester. Avoid prolonged exposure to moisture and light.
• Disposal: Dispose of waste material in accordance with local, regional, and national environmental regulations. Do not pour organic reagents down the drain.
• First Aid: In case of skin or eye contact, flush immediately with copious amounts of water and seek medical attention if irritation persists. Consult the Safety Data Sheet (SDS) for complete hazard information before use.

Note: A full SDS should be reviewed prior to first use. Contact Aladdin Scientific for the most current SDS documentation for SKU E1369778.

Quality, Purity, and Ordering Information

Aladdin Scientific offers Ethyl 5-(tert-butyl)-1H-pyrazole-3-carboxylate under SKU E1369778. Researchers and procurement teams should note the following when ordering:

• Purity: The purity specification for this product should be confirmed from the current product page or CoA. Typical analytical methods for pyrazole esters include HPLC, NMR (¹H and ¹³C), and GC. Request a CoA batch certificate to verify purity of the specific lot received.
• Available Pack Sizes: Contact Aladdin Scientific or visit the product page for current available quantities and pricing.
• Lead Time: Standard and custom quantities may have different lead times; confirm at the time of ordering.
• Quality Assurance: Aladdin Scientific follows rigorous quality control protocols to ensure batch-to-batch consistency for research reagents. Each shipment is accompanied by quality documentation.
• Custom Synthesis: For larger quantities or custom purity grades, contact Aladdin Scientific's technical sales team for a quotation.

For the most up-to-date product information, pricing, and availability of SKU E1369778, visit the Aladdin Scientific website or contact your regional sales representative.