1. Product Overview
4-Methyl-6-phenyl-N-(2-(piperazin-1-yl)ethyl)pyridazin-3-amine (CAS 956798-78-0) is a pyridazine-based small molecule featuring a pendant N-(2-aminoethyl)piperazine side chain. This bifunctional architecture combines a 4-methyl-6-phenyl substituted pyridazin-3-amine core—known for kinase-inhibitory and GPCR-modulating potential—with a secondary amine-bearing piperazine linker, allowing for further N-alkylation, acylation, or salt formation. It is commonly employed as a key intermediate in the synthesis of multi-target kinase inhibitors and central nervous system (CNS) drug candidates, as well as a scaffold for SAR studies on pyridazine-piperazine hybrids.
2. Key Features and Benefits
• Dual Pharmacophoric Elements: Integrates the pyridazine heterocycle (hydrogen-bond acceptor, metabolic stability) with a flexible piperazine-ethylamine arm (improves aqueous solubility and provides a handle for further derivatization).
• Basic Secondary Amine: The terminal piperazine nitrogen (pKa ~9.16 predicted) can be protonated for salt formation or used in amide/urea linkage to bioactive warheads.
• High Purity Supply: ≥98% (HPLC), with full lot-specific CoA including ¹H NMR verification.
• Air-Stable Solid: Low hygroscopicity when stored properly; convenient for weighing and multi-step synthesis.
• Predictable Physicochemical Profile: Calculated LogP ~2.1 and PSA ~53 Ų, consistent with good membrane permeability in drug-like molecules.
3. Major Applications
• Drug Discovery / Medicinal Chemistry: Used in the assembly of pyridazine-containing kinase inhibitors (e.g., c-Met, VEGFR, CDK families) and serotonin/dopamine receptor modulators.
• Heterocyclic Library Synthesis: Serves as a building block for Diversity-Oriented Synthesis (DOS) of N-heterocyclic compound libraries in lead optimization.
• CNS Active Compound Scaffolds: The piperazine moiety is a classic feature in atypical antipsychotics and antidepressant scaffolds; this compound enables systematic SAR exploration.
• Academic Research: Studied as a representative pyridazine-piperazine conjugate in heterocyclic chemistry and supramolecular assembly.
4. Technical Specifications
Item Description
Product Name 4-Methyl-6-phenyl-N-(2-(piperazin-1-yl)ethyl)pyridazin-3-amine
Synonyms 3-Pyridazinamine, 4-methyl-6-phenyl-N-[2-(1-piperazinyl)ethyl]-; N-(2-Piperazin-1-ylethyl)-4-methyl-6-phenylpyridazin-3-amine
CAS Number 956798-78-0
Molecular Formula C₁₇H₂₃N₅
Molecular Weight 297.40 g/mol
MDL Number MFCD22418606
Assay (Purity) ≥98% (HPLC)
Appearance Off-white to light yellow crystalline solid or powder
Melting Point Not reported (amorphous tendency; typical range 90–130 °C for analogs)
Boiling Point ~545.0 ± 50.0 °C (Predicted)
Density 1.130 ± 0.06 g/cm³ (Predicted)
pKa (Predicted, piperazine N) 9.16 ± 0.10
Calculated LogP ~2.11
Polar Surface Area (PSA) 53.08 Ų
Solubility Soluble in: DMSO (~50 mg/mL), Methanol, Ethanol, DCM, Chloroform, Acetic acid.
Slightly soluble in: EtOAc, THF.
Practically insoluble in: Water (free base); soluble as hydrochloride salt in dilute acidified aq. buffer.
SMILES CC1=CC(=NN=C1NCCN2CCNCC2)C3=CC=CC=C3
InChI Key KZXQFWERJERVQT-UHFFFAOYSA-N
Storage (Powder) Inert atmosphere (N₂/Ar), 2–8 °C, protected from light & moisture; stable ≥18–24 months
HS Code 2933.99.90
5. Storage and Handling
• Storage: Store sealed vial under an inert atmosphere (N₂ or Ar) at 2–8 °C, protected from light and moisture. The free base is stable under these conditions for up to 2 years. For long-term (>12 months), keep in a desiccator.
• Handling: Allow vial to reach room temperature before opening to prevent condensation. Dissolve in anhydrous DMSO, MeOH, or DCM as required. The secondary amine may form salts with acidic impurities—use freshly opened solvents.
• Solution Prep: Stock solutions in DMSO (10–50 mM) are stable at -20 °C for short periods (1–2 weeks); avoid repeated freeze-thaw. For aqueous work, convert to hydrochloride salt by adding 1 eq. HCl in MeOH or EtOH, then evaporate.
6. Safety Summary (SDS Highlights)
• GHS Classification: GHS07 – Warning
• Signal Word: Warning
• Hazard Statements:
• H302: Harmful if swallowed.
• H315: Causes skin irritation.
• H319: Causes serious eye irritation.
• H335: May cause respiratory irritation.
• Precautionary Statements:
• P261: Avoid breathing dust/mist/vapors. Use only in a well-ventilated area or fume hood.
• P264: Wash hands, forearms, and face thoroughly after handling.
• P270: Do not eat, drink, or smoke in areas where this material is used.
• P271: Use only outdoors or in a well-ventilated area.
• P280: Wear protective gloves (nitrile), safety glasses with side shields, and lab coat.
• P301+P312: IF SWALLOWED: Call a POISON CENTER or physician if you feel unwell.
• P302+P352: IF ON SKIN: Wash with plenty of soap and water.
• P304+P340: IF INHALED: Remove person to fresh air and keep comfortable for breathing.
• P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.
• P330: Rinse mouth if swallowed.
• P337+P313: If eye irritation persists: Get medical advice/attention.
• P403+P233: Store in a well-ventilated place. Keep container tightly closed.
• P501: Dispose of contents/container in accordance with local/regional regulations.
• First Aid:
• Inhalation: Move to fresh air; if breathing difficult, administer oxygen and seek medical attention.
• Skin Contact: Wash with soap and water; remove contaminated clothing; seek medical advice if irritation develops.
• Eye Contact: Flush immediately with copious water for ≥15 min; remove contact lenses; seek medical attention.
• Ingestion: Rinse mouth; do NOT induce vomiting; seek medical advice.
• Fire-Fighting: Use water spray, alcohol-resistant foam, dry chemical, or CO₂. Wear self-contained breathing apparatus.
• Spill Response: Avoid dust formation. Sweep up and place in a closed container for disposal. Do not allow entry to drains.
• Intended Use: For laboratory research and development ONLY. Not for human or veterinary therapeutic, diagnostic, or food use.
