1. Product Overview
4-(6-Hydrazinylpyrimidin-4-yl)morpholine (CAS No. 5767-36-2) is a morpholine-substituted pyrimidine bearing a terminal hydrazine group at the C6 position of the pyrimidine ring. Supplied at minimum 97% purity (HPLC), this white to off-white crystalline solid is a versatile heterocyclic building block in medicinal chemistry and agrochemical research. The molecule combines a morpholine moiety—known for improving aqueous solubility and pharmacokinetic properties—with a reactive hydrazine functionality that readily undergoes condensation with carbonyl compounds (aldehydes, ketones, β-diketones, β-ketoesters) to form hydrazones, pyrazoles, triazolopyrimidines, and other fused nitrogen heterocycles. It is widely employed in scaffold hopping, library generation, and the synthesis of bioactive molecules targeting kinases, antifolate pathways, and microbial enzymes.
2. Key Features and Advantages
• High Purity & Reproducibility — Minimum 97% purity verified by HPLC and ¹H NMR, ensuring clean cyclocondensation and minimal side products in multi-step sequences.
• Dual Functional Motifs — Morpholine at C4 enhances solubility and serves as a classical pharmacokinetic modifier; the C6-hydrazine is a powerful nucleophile/condensation partner for constructing fused pyrimidine derivatives.
• Versatile Heterocycle Former — Enables one-pot or stepwise synthesis of pyrazolo[3,4-d]pyrimidines, triazolopyrimidines, hydrazone-linked conjugates, and Schiff-base ligands via reaction with aldehydes, 1,3-dicarbonyls, or isocyanates.
• Privileged Pyrimidine Core — Pyrimidine is a core heterocycle in nucleic acids, antifolates (e.g., pemetrexed analogues), and many FDA-approved drugs; this building block accelerates SAR exploration around the 4-morpholino-6-hydrazinopyrimidine scaffold.
• Stable Crystalline Solid — Melting point ~166–168°C; good shelf stability as a dry solid under recommended cool, dry storage, facilitating accurate weighing and long-term use.
3. Main Applications
• Medicinal Chemistry & Drug Discovery — Used to build pyrazolo[3,4-d]pyrimidine kinase inhibitors, antifolate agents, antimicrobial scaffolds, and CNS-active compounds; ideal for diversity-oriented synthesis and fragment-based lead optimization.
• Heterocyclic Library Synthesis — Employed in academic and CRO settings to generate focused libraries of fused pyrimidines via cyclocondensation with aldehydes (→ hydrazones → triazolopyrimidines), 1,3-dicarbonyls (→ pyrazolopyrimidines), and acyl chlorides/isocyanates (→ acylhydrazides → triazoles).
• Coordination Chemistry & Materials — The hydrazine and pyrimidine N atoms can act as multidentate ligands for transition metals, supporting synthesis of metal complexes with catalytic or luminescent properties.
• Agrochemical Research — Pyrimidine-morpholine hybrids appear in herbicidal and fungicidal leads; this intermediate supports early-stage screening of crop-protection candidates.
4. Technical Specifications
5. Storage and Handling
• Storage Temperature — Store at 2–8°C in a cool, dry place. For long-term storage (>12 months), keep in a tightly sealed container under an inert atmosphere (argon or nitrogen) to prevent oxidation of the hydrazine group and moisture uptake.
• Packaging Options — Available in 100 mg, 250 mg, 500 mg, 1 g, 5 g, and bulk quantities upon request.
• Handling Precautions — Use standard laboratory PPE (safety glasses, nitrile gloves, lab coat). Avoid dust generation; handle in a well-ventilated area or fume hood. The hydrazine group is moderately reactive—minimize exposure to strong oxidizers, aldehydes/ketones (unless intentionally condensing), and elevated temperatures during routine handling.
• Shelf Life — When stored as recommended (sealed, 2–8°C, dry, inert atmosphere), the product maintains ≥97% purity for at least 24 months from the date of manufacture. Allow sealed container to reach room temperature before opening to prevent condensation on the hydrazine-containing solid.
6. Safety Overview
• Hazard Classification (GHS) — GHS07 signal word “Warning”; typical hydrazine derivatives may carry H315 (skin irritation), H319 (eye irritation), H335 (respiratory irritation). Not classified as acutely toxic or carcinogenic under standard criteria, but hydrazines can be sensitizers; intended strictly for research and industrial synthesis, not for human/veterinary therapeutic use or as a food additive.
• First Aid Measures — Skin contact: wash thoroughly with soap and water. Eye contact: rinse immediately with plenty of water for ≥15 min, lifting eyelids; seek medical attention if irritation persists. Inhalation: move to fresh air; if breathing difficulty occurs, administer oxygen and consult a physician. Ingestion: rinse mouth, do NOT induce vomiting; seek medical advice.
• Firefighting Measures — Combustible solid. Use water spray, dry chemical, carbon dioxide, or alcohol-resistant foam. Wear self-contained breathing apparatus and full protective gear if involved in fire. Avoid contact with strong oxidizers (risk of exothermic hydrazine oxidation).
• Disposal Considerations — Dispose as nitrogen-containing organic chemical waste in accordance with local, regional, and national regulations. Hydrazine derivatives require controlled disposal—do not discharge to drains, waterways, or soil. Contaminated packaging should be emptied and sent for licensed chemical-waste disposal.
