what is 4-amino-6-chloro-1,3-benzenedisulfonamide used for?

FAQ 2025-04-09

4-amino-6-chloro-1,3-benzenedisulfonamide, also known as **dexamethasone-related naming confusion here is clarified as it’s actually a distinct compound (often referred to as 4-amino-6-chloro-1,3-benzene disulfonamide or chloraminophenamide in industry), is primarily utilized as a pharmaceutical intermediate.

Key Applications

  1. Synthesis of Hydrochlorothiazide:
    • It serves as a critical intermediate in the production of hydrochlorothiazide, a widely prescribed diuretic and antihypertensive agent. Hydrochlorothiazide is used to manage conditions such as hypertension and edema by inhibiting sodium reabsorption in the kidneys.
  2. Organic Synthesis:
    • The compound acts as a reagent or catalyst in organic synthesis reactions, particularly in the preparation of aromatic compounds. Its sulfonamide functional groups enable selective reactions and modifications in complex molecular structures.
  3. Antimicrobial Activity:
    • While not a primary antimicrobial agent, its structure exhibits limited antibacterial properties, which may be leveraged in certain specialized formulations or research contexts.

Physical and Chemical Properties

  • Appearance: White to pale yellow crystalline solid.
  • Solubility: Poorly soluble in water but soluble in organic solvents like ethanol and chloroform.
  • Molecular Formula: C₆H₈ClN₃O₄S₂.
  • Molecular Weight: 285.73 g/mol.
  • Melting Point: 257–261 °C.

Industrial and Research Context

  • Industrial Grade: Supplied in various purities (e.g., 98%) for pharmaceutical manufacturing.
  • Research Use: Employed in academic and industrial laboratories for exploring new synthetic pathways or optimizing existing processes.

Safety and Handling

  • Toxicity: Classified as toxic (T: Toxic) with specific risk phrases (e.g., R23/24: Toxic by inhalation and in contact with skin).
  • Safety Precautions: Requires strict adherence to safety protocols, including the use of protective equipment and proper ventilation.