Written by samir » Updated on: July 10th, 2025
Overview
1-Boc Piperazine (tert-Butyl 4-piperazinecarboxylate) is an essential protected derivative of piperazine, commonly used in pharmaceutical R&D, combinatorial chemistry, and intermediate synthesis. Its primary value lies in its selectively protected nitrogen atom, which makes it an ideal substrate for further functionalization without affecting the entire piperazine ring.
Chemical and Physical Properties
Chemical Name: 1-(tert-Butoxycarbonyl)piperazine
Synonyms: Boc-piperazine, tert-butyl piperazine-1-carboxylate
Molecular Formula: C9H18N2O2
Molecular Weight: 186.25 g/mol
CAS Number: 57260-71-6
Appearance: White to pale yellow crystalline powder
Boiling Point: Approx. 335°C (decomposes)
Solubility: Freely soluble in common organic solvents like dichloromethane (DCM), acetonitrile, and methanol
Its structure contains a six-membered piperazine ring substituted with a Boc protecting group on one nitrogen. This feature ensures regioselective reactivity, ideal for stepwise synthesis in both industrial and academic labs.
Synthesis of 1-Boc Piperazine
1-Boc Piperazine is synthesized by reacting piperazine with di-tert-butyl dicarbonate (Boc₂O) under basic conditions (commonly with triethylamine or sodium bicarbonate). This selective reaction introduces the Boc group to one nitrogen atom, leaving the other available for further modification. The Boc group is acid-labile, meaning it can be easily removed with trifluoroacetic acid (TFA) or HCl in dioxane — a common step in deprotection strategies.
Pharmaceutical and Industrial Applications
1. Intermediate for Drug Molecules
Piperazine-based compounds appear in over 20 approved drugs, such as:
Ciprofloxacin (antibiotic)
Risperidone (antipsychotic)
Sildenafil (vasodilator)
Dasatinib (anticancer)
1-Boc Piperazine serves as a protected precursor, simplifying the synthetic route to such molecules by providing clean, reproducible, and controlled substitution.
2. Lead Optimization & Structure-Activity Relationship (SAR) Studies
Due to its solubility and flexibility, medicinal chemists use 1-Boc Piperazine during lead generation and SAR exploration. It contributes to better:
Receptor binding affinity
Lipophilicity tuning
Solubility improvements
Metabolic stability
3. Scaffold in Peptidomimetics and Macrocycles
1-Boc Piperazine is widely used in macrocyclic drugs and peptidomimetic design, where its nitrogen atoms and ring flexibility help mimic natural peptides. These features are essential for creating protease inhibitors, antiviral agents, and enzyme blockers.
Advantages of Boc Protection
The Boc group offers:
Stability during base-sensitive reactions
Easy deprotection under mild acid
Increased synthetic selectivity
Minimized side reactions during multi-step synthesis
Its compatibility with automated synthesis platforms makes it indispensable for combinatorial chemistry libraries.
Storage and Handling
Shelf-life: Stable under normal conditions if kept dry and away from light
Storage Temperature: 2°C – 8°C recommended for extended shelf life
Hazards: May cause irritation; not considered highly toxic
Precautions: Use gloves, lab coat, and goggles; handle in well-ventilated area
Always refer to the Material Safety Data Sheet (MSDS) for proper handling guidelines.
Packaging and Availability
Offered by chemical suppliers in:
Research packs: 1g, 5g, 25g, 100g
Bulk & commercial lots: 1kg, 5kg, 25kg, with custom contract manufacturing available
Documentation: Supplied with COA, MSDS, TDS, and batch analysis reports. Export supported globally with REACH & ISO compliance as required.
Conclusion
1-Boc Piperazine is an indispensable tool for organic and medicinal chemists. Its protected structure, ease of functionalization, and pharmacological relevance make it a go-to intermediate in the development of next-generation therapeutics. Whether you're working in drug discovery, process chemistry, or academic research, this versatile compound supports innovation with efficiency, flexibility, and reproducibility.
Applications of 1-Boc Piperazine
1. Pharmaceutical Intermediate
1-Boc Piperazine plays a critical role in the synthesis of active pharmaceutical ingredients (APIs). It is frequently used in the preparation of:
Antipsychotic drugs
Antidepressants
Anti-inflammatory agents
Anticancer molecules
By protecting one of the nitrogen atoms on the piperazine ring, it allows for controlled modification of the other, which is essential in stepwise drug synthesis.
2. Medicinal Chemistry & Lead Optimization
In drug discovery and medicinal chemistry, 1-Boc Piperazine is commonly incorporated into combinatorial libraries for screening biological activity. The piperazine scaffold is highly valued for:
Enhancing water solubility
Improving membrane permeability
Acting as a bioisostere for amines or peptides
The Boc group can be easily removed using acid (e.g., TFA), providing flexibility in late-stage functionalization.
3. Peptidomimetic Design
Piperazine-based compounds like 1-Boc Piperazine are often used in the design of peptidomimetics. These are compounds that mimic peptide structures but are more stable and resistant to enzymatic degradation. 1-Boc Piperazine helps in creating:
Enzyme inhibitors
Receptor antagonists
Molecular probes
This application is particularly important in the development of drugs targeting GPCRs, kinases, and enzymatic pathways.
Safety and Handling
Hazard Classification: Low; may cause irritation upon direct contact
Handling Precautions: Use appropriate PPE (gloves, goggles); handle in a fume hood if large volumes are used
Storage Conditions: Store in a tightly sealed container, away from strong acids and heat sources; recommended storage temperature: below 25°C
Packaging and Availability
1-Boc Piperazine is available in:
Lab Packs: 5g, 25g, 100g
Bulk Quantities: 500g, 1kg, 5kg, and customized packaging on request
All batches come with COA, MSDS, and batch-specific documentation. Shipping is available worldwide.
Conclusion
1-Boc Piperazine is a strategically important intermediate in modern chemical synthesis, especially for pharmaceutical applications. Its combination of a reactive piperazine ring and a removable Boc group makes it a go-to building block for chemists involved in drug discovery, peptide chemistry, and heterocycle design. Its ease of use, stability, and broad reactivity spectrum continue to make it a valuable compound in both research and commercial manufacturing.
Need technical documents or a price quote? Contact us today for detailed specifications, bulk availability, and application support.https://www.lifechempharma.com/product/1-boc-piperazine/
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