Ethyl Piperazine-1-Carboxylate: Beyond the Basics

Historical Development

Ethyl Piperazine-1-Carboxylate started making noise in laboratories back in the mid-20th century, tracing its path along with synthetic organic chemistry's rapid advancements. Chemists started with the broader family of piperazine derivatives, aiming to add structure and function to otherwise straightforward molecules. Over the decades, people working in medicinal chemistry realized the value of piperazine rings in developing pharmaceuticals. Adding the ethyl carboxylate group was more than a random tweak — it adjusted solubility, reactivity, and biological interactions in useful ways. The evolution of its synthesis paralleled growth in pharmaceutical demand, as more labs wanted building blocks offering controlled reactivity for drug scaffolds, crop protection molecules, and specialty materials.

Product Overview

Ethyl Piperazine-1-Carboxylate sits on a shelf as a colorless to pale yellow liquid or sometimes as a crystalline solid, depending on its storage conditions. It's used by chemists looking for a flexible intermediate, often thrown into the mix for various alkylation, acylation, or cyclization reactions. In medicinal chemistry, this compound helps build libraries of drug candidates. Technical teams familiar with pharmaceutical APIs and fine chemicals routinely recognize this molecule as indispensable for complex synthesis, especially in heterocycle-rich products.

Physical & Chemical Properties

Density figures often run close to 1.06 g/cm³ at room temperature, with a melting point around −15°C and a boiling point that hovers just above 250°C, often near 260°C. It dissolves well in standard organic solvents like dichloromethane, ethyl acetate, and acetonitrile, which comes in handy for downstream processing. The molecule isn’t particularly volatile or reactive with air, but it can show sensitivity toward strong acids or bases. That piperazine ring locks in conformational flexibility, while the ethyl carboxylate tail brings a measure of lipophilicity.

Technical Specifications & Labeling

Chemicals in this class must meet purity standards set by regulatory agencies and in-house protocols. Reputable suppliers usually provide a COA (Certificate of Analysis) that lists minimum purity—often over 98% for pharmaceutical work—as well as important details like water content, residual solvents, and spectral data from NMR, IR, and LC-MS. The UN proper shipping name, hazard pictograms, batch number, and shelf-life also show up on each bottle, matching GHS requirements. If prepared for research, the label reminds users of its intended use—never for food, drug, or cosmetic applications.

Preparation Method

People working in process chemistry synthesize Ethyl Piperazine-1-Carboxylate using ethyl chloroformate and piperazine under mild alkaline conditions, with solvents like dichloromethane or tetrahydrofuran helping to control exotherms. Reaction temperatures stay cool—ice bath to room temperature—because alkylation can run away if left unchecked. After the reaction, the mixture gets washed with brine, dried, and then concentrated, with chromatography or distillation applied as needed to yield a clean product. It’s efficient, but still demands a careful hand, especially at scale.

Chemical Reactions & Modifications

This compound offers an eye-opening set of downstream possibilities. Chemists often convert the ethyl ester group into other functionalities—hydrolyzing to the acid, coupling with amines to give amides, or reducing to alcohols. The piperazine ring tolerates alkylation and acylation on the secondary amine, which means it can serve as a linchpin for even more decorated molecules. In some setups, protecting groups on the nitrogen make selective chemistry easier, letting researchers fine-tune which part of the molecule reacts next. Because piperazine derivatives show up in antifungals, antivirals, and antipsychotics, this building block often appears in lead optimization campaigns across multiple therapeutic areas.

Synonyms & Product Names

Ethyl Piperazine-1-Carboxylate goes by a handful of names in catalogs and papers. Piperylate, N-Ethoxycarbonylpiperazine, and Ethyl 1-piperazinecarboxylate pop up most frequently. Some inventory systems shorten it to EPC, while others stick with long names to avoid confusion. Academic and industry researchers trade these synonyms based on their SOPs, but CAS numbers and structural diagrams always take priority for traceability and safety.

Safety & Operational Standards

Working with Ethyl Piperazine-1-Carboxylate in the lab requires solid ventilation. Direct skin or eye contact triggers irritation, and inhaling vapors—especially during large-scale synthesis—can provoke respiratory or mucosal effects. Gloves, lab coats, and goggles always show up in SOPs, while fume hoods and spill kits sit nearby. Waste streams feed into designated containers for halogenated solvents and amines, since unchecked drainage sets off compliance alarms and environmental headaches. Emergency shower and eyewash stations form part of the safety net. For shipping, the product travels in high-integrity, labeled packaging to dodge leaks or unauthorized access.

Application Area

Ethyl Piperazine-1-Carboxylate sits at the crossroads of pharma, crop research, and specialty chemicals. Drug development teams turn to it for building kinase inhibitors, serotonin antagonists, and antifungal agents, linking its flexible chemistry to a wide roster of potential therapies. Agrochemical companies explore derivatives for new pesticides and herbicides, betting on the piperazine motif to yield better selectivity and lower toxicity. Polymer and dye manufacturers tool around with it to add nitrogen-containing groups, which can change solubility, dye uptake, or thermal properties. Across these industries, scientists leverage it not because it’s trendy, but because it gets results they can show to regulators, supervisors, and investors.

Research & Development

R&D teams push Ethyl Piperazine-1-Carboxylate into new synthetic routes chasing better yields, greener methods, and novel classes of bioactive compounds. Labs report using enzymatic ester hydrolysis and solvent-free conditions to cut waste and boost atom economy. Medicinal chemists build structure-activity relationships using analogs to map biological activity, aiming to land on winners for clinical trials. Analytical scientists working on process impurities hone new chromatographic techniques to guarantee purity and reproducibility. Research papers now discuss computer-aided design for piperazine derivatives, based on AI models that predict reaction outcomes and biological effects.

Toxicity Research

Mouse and rat studies on piperazine derivatives set red lines for allowable doses and workplace exposure. Acute toxicity appears mild to moderate, with oral LD50 values in the hundreds of milligrams per kilogram, though the exact number shifts depending on the modification. Chronic exposure data runs thin, which leaves employers defaulting to stricter limits and stronger PPE to keep staff out of the crosshairs. In cell assays, this molecule and its close cousins show variable cytotoxicity, demanding care in scaling up or switching from bench to pilot plant. Safety data sheets point out risks tied to amine-based compounds, including potential for sensitization and organ-system effects—making regular air monitoring and health surveillance a good investment.

Future Prospects

Rising demand for innovative drug scaffolds and sustainable agrochemicals keeps Ethyl Piperazine-1-Carboxylate in the R&D spotlight. Advances in flow chemistry and automation hint at faster, safer synthesis. Companies keep funding alternative preparation routes—enzymatic catalysis, electrochemical methods, greener solvents—that bring lower footprints and better yields. With regulatory agencies tightening scrutiny on impurity profiling, future work on purification, analytical method validation, and life-cycle assessment is set to ramp up. Clinical and environmental studies on downstream products will likely bring sharper clarity on safe use, opening the door to new applications in diagnostics, biomaterials, and smart polymers.




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Ethyl Piperazine-1-Carboxylate
Ethyl Piperazine-1-Carboxylate
Ethyl Piperazine-1-Carboxylate