tert-Butyl 4-(4-Aminophenoxy)piperazine-1-carboxylate (CAS 22047-25-2) 98% White to Off-White Crystalline Powder | N-Boc Protected Piperazine Deriva

1. Product Overview

tert-Butyl 4-(4-aminophenoxy)piperazine-1-carboxylate (CAS 22047-25-2) has molecular formula C₁₉H₃₀N₃O₃ and MW 348.47 g/mol. It is an N-Boc-protected piperazine bearing a para-aminophenoxy substituent. The Boc group masks the piperazine nitrogen, preventing undesired quaternization or side reactions during coupling steps, and can be removed under mild acidic conditions (TFA, HCl/dioxane) to regenerate the mono-N-H piperazine. This compound is used as a building block for introducing the piperazine-phenoxy motif in synthetic research.

2. Key Features and Benefits

• Boc-Protected Piperazine: Stable to base and nucleophiles; clean deprotection with TFA or 4M HCl/dioxane.

• Aminophenoxy Handle: The terminal aromatic NH₂ enables further amide/imine formation or diazotization in multi-step sequences.

• Rigid Six-Membered N-Heterocycle: Commonly employed as a scaffold in library synthesis and ligand design studies.

• High Purity: Supplied ≥98% (HPLC), suitable for parallel synthesis and medicinal chemistry research support.

3. Major Applications

• Organic Synthesis: Building block for sequential deprotection (Boc removal → N-alkylation/coupling) and phenoxy-amine functionalization.

• Library / SAR Studies: Introduces piperazine-phenoxy-aryl amine fragment into lead-like structures in academic research.

• Protecting Group Chemistry: Demonstrates orthogonal deprotection strategy (Boc vs Fmoc vs Cbz) in polyfunctional molecules.

• Analytical Reference: Used as a standard in HPLC/LC-MS method development for piperazine derivative quantification.

4. Technical Specifications

Item Description
Product Name tert-Butyl 4-(4-Aminophenoxy)piperazine-1-carboxylate
Synonyms 1-Boc-4-(4-aminophenoxy)piperazine; N-Boc-4-(4-aminophenoxy)piperazine; tert-Butyl 4-(4-aminophenyl)piperazin-1-yl ether carboxylate
CAS Number 22047-25-2
Molecular Formula C₁₉H₃₀N₃O₃
Molecular Weight 348.47 g/mol
MDL Number MFCD00236248
PubChem CID 10390719
Assay (Purity) ≥98% (HPLC)
Appearance White to off-white crystalline powder
Melting Point 148–152 °C
Boiling Point ~524 °C (Estimated)
Density ~1.13 g/cm³ (Estimated)
Calculated LogP ~2.5–3.0
Polar Surface Area (PSA) ~66.8 Ų
Hydrogen Bond Donors 1 (aniline NH₂)
Hydrogen Bond Acceptors 6 (3×O Boc/ether, 2×N piperazine, 1×O phenoxy)
Rotatable Bonds 5
Solubility Soluble in DMSO, DMF, dichloromethane, ethyl acetate, methanol (slight warming); poorly soluble in water/hexane.
SMILES CCOC(=O)N1CCN(c2ccc(N)cc2)CC1
InChI Key InChIKey (PubChem): QZXKPVJIFMFXQM-UHFFFAOYSA-N — verify via database
Storage 2–8 °C or RT, sealed, protect from light & moisture; stable ≥24 months
HS Code 2933.59.90 / 3822.90.00

5. Storage and Handling

Store in a tightly sealed container at 2–8 °C or room temperature, protected from light and moisture. The aniline NH₂ is generally stable but may darken slightly on prolonged air exposure—store dry. For Boc deprotection, treat with TFA in DCM (15–30 min, rt) or 4 M HCl in 1,4-dioxane, then neutralize/crash out. Dissolve in DMSO, DMF, or DCM for coupling reactions. Avoid strong oxidizing agents.

6. Safety Summary

• GHS Classification: GHS07 – Warning

• Signal Word: Warning

• Hazard Statements: H315 (Causes skin irritation), H319 (Causes serious eye irritation), H335 (May cause respiratory irritation)

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