1-Acetyl-4-(4-hydroxyphenyl)piperazine (CAS 67914-60-7) 98% White to Off-White Crystalline Powder | N-Acetyl Piperazine Derivative / Heterocycle Bui

1. Product Overview

1-Acetyl-4-(4-hydroxyphenyl)piperazine (CAS 67914-60-7) has the molecular formula C₁₂H₁₆N₂O₂ and molecular weight 220.27 g/mol. It is an N-acetylated piperazine bearing a para-hydroxyphenyl substituent, serving as a protected form of 1-(4-hydroxyphenyl)piperazine (HPP). The acetyl group can be removed under mild acidic or basic hydrolysis to regenerate the parent secondary amine. This compound is used as a building block in the synthesis of substituted piperazines, phenolic ligands, and N-heterocyclic libraries.

2. Key Features and Benefits

• Protected Phenolic Piperazine: The secondary amine of HPP is blocked as an N-acetyl derivative—stable to many reaction conditions, removable by acid/base hydrolysis.

• Phenolic OH Handle: Enables O-alkylation, esterification, or ether formation for appending additional functionality.

• Piperazine Scaffold: Widely employed in medicinal chemistry SAR studies and ligand design as a rigid six-membered N-heterocycle.

• High Purity: Supplied ≥98% (HPLC), suitable for multi-step synthesis and library construction.

3. Major Applications

• Organic Synthesis: Building block for deprotection to 1-(4-hydroxyphenyl)piperazine, followed by N- or O-functionalization.

• Heterocycle / Library Synthesis: Used in parallel synthesis of substituted piperazine derivatives for structure–activity relationship studies.

• Coordination / Material Chemistry: Phenolic OH and tertiary N serve as potential ligand donor sites in metal complexation research.

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

4. Technical Specifications

Item Description
Product Name 1-Acetyl-4-(4-hydroxyphenyl)piperazine
Synonyms N-Acetyl-4-(4-hydroxyphenyl)piperazine; 1-[4-(4-Hydroxyphenyl)piperazin-1-yl]ethanone
CAS Number 67914-60-7
Molecular Formula C₁₂H₁₆N₂O₂
Molecular Weight 220.27 g/mol
MDL Number MFCD00052047
PubChem CID 3082659
Assay (Purity) ≥98% (HPLC)
Appearance White to off-white or pale pinkish crystalline powder
Melting Point 178–182 °C
Boiling Point ~361 °C (Estimated)
Density ~1.18 g/cm³ (Estimated)
pKa (Predicted) ~9.8 ± 0.3 (piperazine N⁺H); ~10.0 ± 0.5 (phenol OH)
Calculated LogP ~0.3–1.0
Polar Surface Area (PSA) ~43.8 Ų
Hydrogen Bond Donors 1 (phenolic OH)
Hydrogen Bond Acceptors 4 (C=O, 2×N-piperazine O, phenol O)
Rotatable Bonds 2
Solubility Soluble in DMSO, methanol, ethanol, dichloromethane, ethyl acetate; slightly soluble in water (pH-dependent, more soluble as sodium phenoxide).
SMILES CC(=O)N1CCN(c2ccc(O)cc2)CC1
InChI Key AGVNLFCRZULMKK-UHFFFAOYSA-N
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 phenolic OH may slowly oxidize on prolonged air exposure—store dry. For deprotection, treat with aqueous HCl or NaOH (caution: don't overheat phenol). Dissolve in DMSO, MeOH, or EtOH for reactions; aqueous buffers may be used at neutral-to-slightly acidic pH for short-term solution work.

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)

• Precautionary Statements: P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P332+P313, P337+P313, P362, P403+P233, P501

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