1. Product Overview
5-Bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (CAS No. 478828-53-4) is a brominated indazole derivative bearing a tetrahydro-2H-pyran-2-yl (THP) protecting group at the N1 position. Supplied at minimum 95% purity (HPLC), this white to off-white solid is a key protected heterocyclic building block in medicinal chemistry and pharmaceutical process research. The THP group provides robust N-protection during multi-step synthesis and can be readily removed under mild acidic conditions, while the C5 bromine serves as an excellent handle for palladium-catalyzed cross-couplings (Suzuki, Sonogashira, Buchwald–Hartwig) to introduce diverse aryl, alkynyl, or amino substituents. This compound is extensively used in the construction of indazole-containing drug candidates targeting kinases, GPCRs, and other therapeutic targets where the indazole core is a privileged scaffold.
2. Key Features and Advantages
• High Purity & Consistency — Minimum 95% purity verified by HPLC and supported by ¹H NMR; suitable for sensitive biological assays and scale-up synthesis.
• Orthogonal Protection Strategy — The THP N-protecting group is stable to bases and nucleophiles but cleanly removed with dilute acetic acid or p-TsOH, enabling selective deprotection without affecting other functionalities.
• Versatile Cross‑Coupling Handle — The C5 bromine allows efficient Pd‑catalyzed diversifications to generate indazole libraries for SAR studies and lead optimization.
• Privileged Indazole Scaffold — Indazole is a widely adopted heterocycle in FDA‑approved drugs (e.g., pazopanib, ruxolitinib analogues); this protected bromo‑indazole accelerates route design for such targets.
• Stable Solid Form — Exhibits good shelf stability as a dry solid under recommended cool, dry storage, minimizing decomposition and supporting reproducible multi‑step workflows.
3. Main Applications
• Medicinal Chemistry & Drug Discovery — Used as a core intermediate for synthesizing indazole‑based kinase inhibitors, anti‑inflammatory agents, anticancer leads, and CNS‑targeting compounds; ideal for fragment‑based and diversity‑oriented synthesis.
• Pharmaceutical Process Development — Serves as a protected indazole synthon in API routes where N‑protection is required to prevent unwanted N‑alkylation or to control regiochemistry during ring functionalization.
• Heterocyclic Library Construction — Employed in academic and CRO/CMO settings to generate focused libraries via Suzuki–Miyaura coupling at C5 followed by THP deprotection, enabling rapid exploration of indazole chemical space.
• Agrochemical & Material Research — The indazole core also appears in pesticide and functional‑material design; this building block supports early‑stage screening of such applications.
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 moisture uptake and slow oxidative degradation.
• 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 THP ether is acid‑sensitive—avoid contact with strong protic acids during routine handling.
• Shelf Life — When stored as recommended (sealed, 2–8°C, dry), the product maintains ≥95% purity for at least 24 months from the date of manufacture. Allow sealed container to warm to room temperature before opening to prevent condensation.
6. Safety Overview
• Hazard Classification (GHS) — GHS07 signal word “Warning”; H315 (causes skin irritation), H319 (causes serious eye irritation), H335 (may cause respiratory irritation). Not classified as acutely toxic or environmentally hazardous under standard criteria; 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.
• Disposal Considerations — Dispose as non‑halogenated organic chemical waste (contains bromine and heteroatom) in accordance with local, regional, and national regulations. Do not discharge to drains, waterways, or soil without pretreatment. Contaminated packaging should be emptied and sent for licensed chemical‑waste disposal.
