1-Boc-Piperazine (CAS 57260-71-6) — also known as tert-butyl piperazine-1-carboxylate or N-BOC-piperazine — is a widely used protected piperazine intermediate in organic synthesis. It plays a critical role in pharmaceutical development, polymer chemistry, and advanced coupling reactions.
What Is 1-Boc-Piperazine?
1-Boc-Piperazine is a chemical compound with the molecular formula C₉H₁₈N₂O₂ and a molecular weight of 186.25 g/mol. Its structure consists of a piperazine ring with a tert-butoxycarbonyl (BOC) protecting group attached to one of the nitrogen atoms.
CAS Number: 57260-71-6
Synonyms: N-BOC-Piperazine, BOC-PAZ, PIBOC, tert-butyl piperazine-1-carboxylate
Appearance: White to light yellow crystalline solid
Melting Point: ~43–47 °C
Key Applications of 1-Boc-Piperazine
1-Boc-Piperazine is valued in research and industrial chemistry for its versatility as a protected amine building block. Its uses include:
Organic synthesis: As an intermediate for constructing more complex molecules.
Buchwald–Hartwig coupling reactions: Reacts with aryl halides to form diarylamine derivatives.
Pharmaceutical intermediates: Useful in synthesizing piperazine-containing drugs and novel bioactive compounds.
Polymer chemistry: Serves as a termination agent in controlled polymerizations like living cationic ring opening polymerization to produce specialized polymers.
General Manufacturing Overview
Manufacturing 1-Boc-Piperazine involves the protection of piperazine with a BOC protecting group. In typical laboratory and industrial contexts, this transformation is accomplished by reacting piperazine with di-tert-butyl dicarbonate (Boc₂O) under controlled conditions.
Typical Manufacturing Steps (Overview Only)
Preparation of Reactants:
Piperazine — the core heterocycle to be protected.
Di-tert-butyl dicarbonate (Boc₂O) — the protecting group donor.
Protection Reaction:
Piperazine is reacted with Boc₂O in an appropriate organic solvent or under solvent-free conditions.
Catalysts such as iodine may be used to promote BOC protection.
Isolation and Purification:
The resulting 1-Boc-Piperazine is purified by standard techniques such as crystallization or distillation.
Final product quality is typically confirmed using analytical methods such as HPLC or NMR.
Note: The exact detailed synthetic procedures (quantities, temperatures, reaction controls, and safety protocols) are proprietary and subject to safety regulations. Proper industrial practices, chemical engineering controls, and compliance with local regulations are required for any chemical manufacture.
Chemical and Physical Properties
| Property | Value |
|---|---|
| Molecular Formula | C₉H₁₈N₂O₂ |
| Molecular Weight | 186.25 g/mol |
| Physical Form | Crystalline solid |
| Appearance | White to light yellow |
| Melting Point | 43–47 °C |
| Solubility | Soluble in DMSO, methanol, ethyl acetate |
| Stability | Air sensitive |
Safety and Handling
1-Boc-Piperazine should be handled with care:
Irritant: Can irritate skin, eyes, and respiratory tract.
Protective Gear: Use gloves, goggles, and appropriate respiratory protection.
Storage: Keep in inert atmosphere and avoid moisture.
Always consult the Safety Data Sheet (SDS) before handling.
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