368-50-3

Usage

Uses

Used in Biochemical Research:
3-Aminobenzenesulfonyl fluoride is used as an inhibitory agent for serine proteases, facilitating the study of their structure and function. Its irreversible binding to the active site of these enzymes allows researchers to gain insights into their mechanisms of action and potential roles in various biological processes.
Used in Pharmaceutical Industry:
3-Aminobenzenesulfonyl fluoride is utilized as a precursor in the synthesis of a variety of compounds with applications in the pharmaceutical sector. Its unique chemical properties and reactivity make it a valuable component in the development of new drugs and therapeutic agents.
Used in Drug Development:
In the drug development process, 3-Aminobenzenesulfonyl fluoride is employed as a key intermediate for creating molecules with potential therapeutic effects. Its role in the synthesis of pharmaceuticals contributes to the advancement of treatments for various diseases and conditions.
Used in Enzyme Inhibition Studies:
3-Aminobenzenesulfonyl fluoride is used as a research tool for studying enzyme inhibition, particularly focusing on serine proteases. This application aids in understanding the interactions between enzymes and their inhibitors, which is crucial for the design of more effective drugs and therapies.
Used in Organic Synthesis:
In the field of organic synthesis, 3-Aminobenzenesulfonyl fluoride is applied as a versatile building block for the creation of complex organic molecules. Its reactivity and functional groups make it suitable for a wide range of synthetic pathways, leading to the production of diverse chemical compounds with various applications.

InChI:InChI=1/C6H6FNO2S/c7-11(9,10)6-3-1-2-5(8)4-6/h1-4H,8H2

Upstream product

• 121-47-1 3-aminobenzenesulfonic acid 
• 349-78-0 3-nitrobenzene-1-sulfonyl fluoride 
• 121-51-7 3-nitrobenzenesulphonyl chloride 

Downstream Products

• 7470-75-9 3-amino-N-(pyrimidin-2-yl)benzenesulfonamide 
• 402-36-8 m-(fluorosulfonyl)phenyl isocyanate 
• 13908-51-5 3-[3-(2-Chloro-ethyl)-ureido]-benzenesulfonyl fluoride 
• 2489-52-3 3-(fluorosulfonyl)benzenesulfonyl chloride 
• 30880-75-2 3-[2-(2-Chloro-4-nitro-phenylsulfanyl)-acetylamino]-benzenesulfonyl fluoride 
• 201336-48-3 3-Amino-N-[4-(3-ethyl-2,6-dioxo-piperidin-3-yl)-phenyl]-benzenesulfonamide 
• 220208-08-2 3-Amino-N-phenoxathiin-2-yl-benzenesulfonamide 
• 351-39-3 (3-fluorosulfonyl-phenyl)-carbamic acid methyl ester 
• 2489-55-6 3-{3-[2-(2-Hexadecyloxy-phenylcarbamoyl)-acetyl]-phenylsulfamoyl}-benzenesulfonyl fluoride 

Relevant academic research and scientific papers

A Broad-Spectrum Catalytic Amidation of Sulfonyl Fluorides and Fluorosulfates**

A broad-spectrum, catalytic method has been developed for the synthesis of sulfonamides and sulfamates. With the activation by the combination of a catalytic amount of 1-hydroxybenzotriazole (HOBt) and silicon additives, amidations of sulfonyl fluorides and fluorosulfates proceeded smoothly and excellent yields were generally obtained (87–99 %). Noticeably, this protocol is particularly efficient for sterically hindered substrates. Catalyst loading is generally low and only 0.02 mol % of catalyst is required for the multidecagram-scale synthesis of an amantadine derivative. In addition, the potential of this method in medicinal chemistry has been demonstrated by the synthesis of the marketed drug Fedratinib via a key intermediate sulfonyl fluoride 13. Since a large number of amines are commercially available, this route provides a facile entry to access Fedratinib analogues for biological screening.

(Chlorosulfonyl)benzenesulfonyl Fluorides - Versatile Building Blocks for Combinatorial Chemistry: Design, Synthesis and Evaluation of a Covalent Inhibitor Library

Multigram synthesis of (chlorosulfonyl)benzenesulfonyl fluorides is described. Selective modification of these building blocks at the sulfonyl chloride function under parallel synthesis conditions is achieved. It is shown that the reaction scope includes the use of (hetero)aromatic and electron-poor aliphatic amines (e.g., amino nitriles). Utility of the method is demonstrated by preparation of the sulfonyl fluoride library for potential use as covalent fragments, which is demonstrated by a combination of in silico and in vitro screening against trypsin as a model enzyme. As a result, several inhibitors were identified with activity on par with that of the known inhibitor.