
Ethyl Piperazine-2-carboxylate
Colorless to pale yellow oily liquid
- Commodity name: Ethyl Piperazine-2-carboxylate
Keywords:
I. Basic Chemical Information
CAS Numbers:
Racemic mixture: 2762-32-5
(S)-Isomer: 133525-04-9
Molecular Formula:C₇H₁₄N₂O₂
Molecular Weight:158.20 g/mol
II. Physicochemical Properties
Appearance: Colorless to pale yellow oily liquid
Boiling Point:120-122 ℃ (0.1 mmHg)
Density: 1.092 g/cm³ (25 ℃)
Refractive Index:n²⁰/D = 1.472
Solubility:
Freely soluble in ethanol, DCM, THF
Slightly soluble in water
Flash Point: 96 ℃ (closed cup)
Chiral Purity:Racemic mixture / (S)-isomer ≥99% ee
III. Core Application Areas
1. Key Intermediate in Pharmaceutical Synthesis
Quinolone Antibiotics:
Esterified precursor for synthesizing Ciprofloxacin
Chiral side-chain module for constructing Gatifloxacin
Antiviral Drugs:
Preparation of HIV protease inhibitors(e.g., piperazine modification unit in Lopinavir)
Neurological Drugs:
Synthesis of 5-HT₃ receptor antagonists(e.g., derivatives of antiemetic drug Ondansetron)
2. Asymmetric Catalytic Ligands
Chiral Auxiliaries:
Hydrolysis to (S)-2-piperazinecarboxylic acid → Preparation of Cu(II) chiral catalysts (for asymmetric Michael addition)
Synthesis of bipiperazine bidentate ligands (for nickel-catalyzed C-S bond coupling)
3. Peptidomimetic Synthesis
Protection Group Strategy:
Boc/Fmoc protection of nitrogen atoms → Solid-phase synthesis of rigid β-turn peptide scaffolds
Application in tumor-targeting peptide drugs (angiotesin receptor inhibitors)
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