1. Product Overview
6-Amino-2,3-dichlorophenol (CAS: 116278-69-4) is a halogenated aminophenol derivative with the molecular formula C₆H₅Cl₂NO and a molecular weight of 178.02 g/mol. This bifunctional aromatic compound bears both an amino (–NH₂) and a hydroxyl (–OH) group on a dichlorinated benzene ring, making it a versatile scaffold in heterocyclic synthesis and pharmaceutical intermediate production. It typically appears as a light beige to off-white crystalline solid at room temperature, with predicted boiling point ~277 °C and density ~1.54 g/cm³. The compound is slightly soluble in water but freely soluble in common organic solvents such as ethanol, DMSO, and acetone.
2. Key Features and Advantages
• High Purity: Routinely supplied at ≥98% purity (HPLC/NMR verified), suitable for sensitive multi-step syntheses.
• Bifunctional Reactivity: Simultaneous presence of –NH₂ and –OH allows selective protection/deprotection strategies and orthogonal derivatization (e.g., diazotization, ether/ester formation, oxidative cyclization).
• Halogen Handles: The 2,3-dichloro pattern enables sequential nucleophilic aromatic substitution or metal-catalyzed cross-coupling after appropriate functional group masking.
• Well-Characterized: Full spectral data (¹H/¹³C NMR, LC-MS, IR) available from certified batches; MDL No. MFCD20693682, PubChem CID 12213215.
• Research-Grade Consistency: Stable under recommended storage; minimal batch-to-batch variation for reproducible SAR and process chemistry work.
3. Main Applications
• Pharmaceutical Intermediates: Used as a key building block in the synthesis of antibacterial agents, kinase inhibitor precursors, and other APIs requiring dichlorinated aminophenol cores.
• Heterocyclic Synthesis: Serves as starting material for benzoxazole, quinoline, and phenoxazine formation via cyclization with carboxylic acids, aldehydes, or ortho-halogenated partners.
• Medicinal Chemistry & SAR: Valuable fragment for library generation in drug discovery, especially in designing small-molecule modulators with halogen-balanced lipophilicity.
• Agrochemical & Dye Intermediates: Employed in the preparation of chlorinated aromatic dyes and crop-protection active ingredients.
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 to prevent oxidation of the phenol and amine groups. For long-term storage, –20 °C under inert gas 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. The compound contains both phenol (corrosive/irritant) and halogenated aromatic amine (potential sensitizer) functionalities—avoid contact with strong oxidizers and acids.
6. Safety Overview
• Hazard Classification: Hazardous under GHS; halogenated aminophenols are irritants and suspected sensitizers.
• Signal Word: Warning
• Hazard Statements: H302 (Harmful if swallowed); H315 (Causes skin irritation); H317 (May cause an allergic skin reaction); H319 (Causes serious eye irritation); H335 (May cause respiratory irritation).
• Precautionary Statements: P261 (Avoid breathing dust); P264 (Wash skin thoroughly after handling); P272 (Contaminated work clothing should not be worn outside the workplace); 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).
• 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.
