4-Chloro-2-fluoro-5-sulfamylbenzoic acid
[CAS# 4793-22-0]

Identification

• Classification: Organic raw materials >> Organic fluorine compound >> Fluorobenzoic acid series
• Name: 4-Chloro-2-fluoro-5-sulfamylbenzoic acid
• Synonyms: 5-(Aminosulfonyl)-4-chloro-2-fluorobenzoic acid
• Molecular Formula: C₇H₅ClFNO₄S
• Molecular Weight: 253.63
• CAS Registry Number: 4793-22-0
• SMILES: C1=C(C(=CC(=C1S(=O)(=O)N)Cl)F)C(=O)O

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

The discovery of 4-chloro-2-fluoro-5-sulfonylbenzoic acid stems from efforts to develop novel sulfonamide compounds with enhanced biological activity. In the mid-20th century, researchers focused on modifying benzoic acid derivatives to enhance their therapeutic potential. The introduction of chlorine and fluorine substituents and sulfonamide groups on the aromatic rings resulted in compounds with desirable physicochemical and pharmacokinetic properties.

The synthesis of such compounds typically involves a multistep process. The appropriate benzoic acid precursor is first chlorinated and fluorinated, followed by the introduction of the sulfonamide. Advanced halogenation and sulfonation techniques are employed to achieve the precise substitution pattern desired for 4-chloro-2-fluoro-5-sulfonylbenzoic acid, highlighting the synthetic complexity of this compound and the need for controlled reaction conditions.

4-Chloro-2-fluoro-5-sulfonylbenzoic acid is of vital importance in medicinal chemistry, especially as an intermediate in the synthesis of diuretics. One prominent application is the synthesis of sulfonamide diuretics, which are used to treat conditions such as hypertension, edema, and heart failure. The sulfonamide group mimics the structure of essential biomolecules, allowing the compound to interact with enzyme targets in the kidney, promoting diuresis and electrolyte balance.

In addition, the unique structural features of 4-chloro-2-fluoro-5-sulfonylbenzoic acid facilitate the design of drugs with specific pharmacological characteristics. The presence of chlorine and fluorine groups affects the lipophilicity and metabolic stability of the compound, becoming a valuable cornerstone in medicinal chemistry to develop drugs with higher efficacy and fewer side effects.

In addition to pharmaceuticals, 4-chloro-2-fluoro-5-sulfonylbenzoic acid can also be used in agrochemicals. Its structure can be used to synthesize herbicides and fungicides, providing an effective solution for controlling unwanted plant growth and crop diseases. The compound is able to disrupt specific biochemical pathways in plants and fungi, making it an effective agent in pesticide formulations.

Ongoing research explores the potential of 4-chloro-2-fluoro-5-sulfonylbenzoic acid in the development of new therapeutic agents and agrochemicals. Research focuses on optimizing its synthesis, exploring novel derivatives, and understanding its interactions with biological targets. Advances in synthetic methods and computational modeling continue to expand the application range of these versatile compounds, driving innovations in medicine and agriculture.

References

none