5-Iodo-1-phenyl-1H-imidazole | CAS 1924616-64-7 | Purity 98% | Pharmaceutical Intermediate & Heterocyclic Building Block

1. Product Overview

5-Iodo-1-phenyl-1H-imidazole (CAS: 1924616-64-7) is an iodinated N‑phenyl imidazole derivative with the molecular formula C₉H₇IN₂ and a molecular weight of 270.07 g/mol. This compound features a reactive iodine atom at the 5‑position of the imidazole ring and a phenyl substituent on the nitrogen (N‑1), making it a versatile electrophile for palladium‑catalyzed cross‑coupling reactions and a key scaffold in heterocyclic and medicinal chemistry. It typically appears as a white to off‑white crystalline solid or powder at room temperature, with a predicted boiling point of ~398 °C and density ~1.75 g/cm³.

2. Key Features and Advantages

• High Purity: Supplied at ≥98% purity (HPLC/NMR verified), ensuring clean conversion in sensitive Pd‑catalyzed couplings without significant dehalogenation.

• Reactive Iodide: The 5‑iodo substituent is highly active in Suzuki–Miyaura, Sonogashira, and Buchwald–Hartwig couplings, enabling straightforward C‑arylation or alkynylation at the imidazole core.

• N‑Phenyl Imidazole Scaffold: Provides a rigid, planar heteroaromatic system widely used in bioactive molecule design, particularly for kinase inhibitors and antifungal agents.

• Orthogonal Reactivity: The imidazole N‑phenyl bond is stable under most coupling conditions, while the C‑I bond can be selectively transformed; the remaining NH site (tautomeric with N‑phenyl form) allows further functionalization if needed via deprotection or alternative regioisomers.

• Consistent Quality: Batches are QC‑tested by ¹H/¹³C NMR, LC‑MS, and melting point; stable under inert atmosphere at low temperature.

3. Main Applications

• Pharmaceutical Intermediates: Used as a building block in the synthesis of imidazole‑based APIs, including antifungal agents (e.g., related to ketoconazole/scaffold), kinase inhibitors, and GPCR modulators.

• Cross‑Coupling Building Block: Employed in Suzuki, Sonogashira, and Stille reactions to introduce aryl/alkynyl groups at the 5‑position of the imidazole ring, facilitating library synthesis for drug discovery.

• Medicinal Chemistry & SAR: Valuable core for structure–activity relationship studies where iodinated imidazoles serve as precursors to diverse substituted analogues.

• Material Science: Used in the preparation of N‑heterocyclic carbene (NHC) precursors and coordination complexes with transition metals, relevant to catalysis and organic electronics.

4. Technical Specifications

5. Storage and Handling

• Storage Conditions: Store in a cool, dry, dark place under inert atmosphere (N₂ or Ar) at 2–8 °C. Keep container tightly sealed and protected from light, as aryl iodides can slowly decompose under UV exposure or at elevated temperature. For long‑term storage (>1 year), –20 °C under argon is recommended.

• Shelf Life: 2 years when stored as recommended.

• Handling Precautions: Use personal protective equipment (nitrile gloves, safety goggles, lab coat). Handle in a fume hood to avoid inhalation of dust. Aryl iodides may release iodine vapour upon heating—avoid open flames and strong oxidizers. The imidazole ring is mildly basic; avoid strong acids without appropriate protection.

6. Safety Overview

• Hazard Classification: Hazardous under GHS; iodinated heteroaromatics are irritants and potential sensitizers.

• Signal Word: Warning

• Hazard Statements: H302 (Harmful if swallowed); H315 (Causes skin irritation); H319 (Causes serious eye irritation); H335 (May cause respiratory irritation); H413 (May cause long‑lasting effects to aquatic life).

• Precautionary Statements: P261 (Avoid breathing dust/fume); P264 (Wash skin thoroughly after handling); P280 (Wear protective gloves/eye protection); P305+P351+P338 (IF IN EYES: rinse cautiously with water for several minutes; remove contact lenses if present; continue rinsing); P273 (Avoid release to the environment).

• Regulatory Notice: For industrial and scientific research use only. Not for human or veterinary medicinal use without further purification and regulatory approval. Dispose as halogen‑containing organic waste per local regulations; do not incinerate in household waste.