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Ethyl Piperazine-2-carboxylate

Colorless to pale yellow oily liquid

  • Commodity name: Ethyl Piperazine-2-carboxylate

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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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