454-93-3

Usage

Uses

Used in Pharmaceutical Industry:
3-(fluorosulphonyl)benzoyl chloride is used as a key intermediate for the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with improved properties, such as enhanced bioavailability, selectivity, and potency.
Used in Agrochemical Industry:
In the agrochemical industry, 3-(fluorosulphonyl)benzoyl chloride serves as a crucial building block for the synthesis of novel agrochemicals. Its incorporation into these compounds can lead to the development of more effective and environmentally friendly pesticides and herbicides.
Used in Organic Synthesis:
3-(fluorosulphonyl)benzoyl chloride is used as a versatile reagent in organic synthesis for the preparation of a wide range of organic compounds. Its unique functional groups enable the formation of various chemical bonds and reactions, facilitating the synthesis of complex organic molecules with diverse applications.
Used in Fluorinated Derivatives Production:
Due to the presence of a fluorine atom, 3-(fluorosulphonyl)benzoyl chloride is used as a precursor for the production of fluorinated derivatives. These derivatives often exhibit unique properties, such as increased stability, reactivity, or selectivity, making them valuable in various applications, including pharmaceuticals, materials science, and chemical research.

InChI:InChI=1/C7H4ClFO3S/c8-7(10)5-2-1-3-6(4-5)13(9,11)12/h1-4H

Upstream product

• 65-85-0 benzoic acid 
• 4025-64-3 3-Carboxybenzenesulfonyl chloride 
• 454-95-5 3-carboxybenzenesulfonyl fluoride 

Downstream Products

• 428-16-0 bis-[4-(3-fluorosulfonyl-benzoylamino)-phenyl]-sulfone 
• 454-94-4 3-carbamoyl-benzenesulfonyl fluoride 
• 2489-54-5 3-{3-[2-(2-Hexadecyloxy-phenylcarbamoyl)-acetyl]-phenylcarbamoyl}-benzenesulfonyl fluoride 
• 2488-51-9 2-(3-Fluorosulfonyl-benzoyl)-3-oxo-butyric acid ethyl ester 
• 80936-69-2 3-(3-Hydroxymethyl-phenylcarbamoyl)-benzenesulfonyl fluoride 
• 80936-67-0 3-(4-Methoxymethyl-phenylcarbamoyl)-benzenesulfonyl fluoride 
• 101314-82-3 5'-deoxy-5'-<3-(fluorosulfonyl)benzamido>thymidine 
• 74547-09-4 3-[2-(6-Oxo-6,9-dihydro-purin-1-yl)-ethylcarbamoyl]-benzenesulfonyl fluoride 
• 74539-08-5 1-<4-<3-(fluorosulfonyl)benzamido>benzyl>hypoxanthine 
• 70950-60-6 5-(3-Fluorosulphonylbenzamido)-1-hydroxy-2-naphthoic acid 

Relevant academic research and scientific papers

Development of Covalent Ligands for G Protein-Coupled Receptors: A Case for the Human Adenosine A3 Receptor

The development of covalent ligands for G protein-coupled receptors (GPCRs) is not a trivial process. Here, we report a streamlined workflow thereto from synthesis to validation, exemplified by the discovery of a covalent antagonist for the human adenosine A3 receptor (hA3AR). Based on the 1H,3H-pyrido[2,1-f]purine-2,4-dione scaffold, a series of ligands bearing a fluorosulfonyl warhead and a varying linker was synthesized. This series was subjected to an affinity screen, revealing compound 17b as the most potent antagonist. In addition, a nonreactive methylsulfonyl derivative 19 was developed as a reversible control compound. A series of assays, comprising time-dependent affinity determination, washout experiments, and [35S]GTPγS binding assays, then validated 17b as the covalent antagonist. A combined in silico hA3AR-homology model and site-directed mutagenesis study was performed to demonstrate that amino acid residue Y2657.36 was the unique anchor point of the covalent interaction. This workflow might be applied to other GPCRs to guide the discovery of covalent ligands.

Sulfur(VI) fluoride compounds and methods for the preparation thereof

This application describes a compound represented by Formula (I): (I) wherein: Y is a biologically active organic core group comprising one or more of an aryl group, a heteroaryl aryl group, a nonaromatic hydrocarbyl group, and a nonaromatic heterocyclic group, to which Z is covalently bonded; n is 1, 2, 3, 4 or 5; m is 1 or 2; Z is O, NR, or N; X1 is a covalent bond or —CH2CH2—, X2 is O or NR; and R comprises H or a substituted or unsubstituted group selected from an aryl group, a heteroaryl aryl group, a nonaromatic hydrocarbyl group, and a nonaromatic heterocyclic group. Methods of preparing the compounds, methods of using the compounds, and pharmaceutical compositions comprising the compounds are described as well.

FLUOROSULFONYL sEH INHIBITORS

Fluorosulfonyl-substituted sEH inhibitors are compounds represented by Formula (I): wherein R1 is selected from the group consisting of alkyl, heteroalkyi, C5-C12 cycloalkyi, C5-C12 cycloalkylalkyi, C5-C12 cycloalkylheteroalkyi, arylalkyi, arylheteroalkyi, aryl, and heteroaryl; and R1 can be substituted or unsubstituted; P1 is a primary pharmacophore; P2 is a secondary pharmacophore; P3 is a tertiary pharmacophore; and L1 and L2 are linking groups. The subscript m has a value of 0 or 1; n has a value of 0 or 1; and the compound of Formula (I) includes at least one S02F ("fluorosulfonyl") group covalently bonded thereto.

Aromatic sulfonyl fluorides covalently kinetically stabilize transthyretin to prevent amyloidogenesis while affording a fluorescent conjugate

Molecules that bind selectively to a given protein and then undergo a rapid chemoselective reaction to form a covalent conjugate have utility in drug development. Herein a library of 1,3,4-oxadiazoles substituted at the 2 position with an aryl sulfonyl fluoride and at the 5 position with a substituted aryl known to have high affinity for the inner thyroxine binding subsite of transthyretin (TTR) was conceived of by structure-based design principles and was chemically synthesized. When bound in the thyroxine binding site, most of the aryl sulfonyl fluorides react rapidly and chemoselectively with the pK a-perturbed K15 residue, kinetically stabilizing TTR and thus preventing amyloid fibril formation, known to cause polyneuropathy. Conjugation t50s range from 1 to 4 min, ～1400 times faster than the hydrolysis reaction outside the thyroxine binding site. X-ray crystallography confirms the anticipated binding orientation and sheds light on the sulfonyl fluoride activation leading to the sulfonamide linkage to TTR. A few of the aryl sulfonyl fluorides efficiently form conjugates with TTR in plasma. Eleven of the TTR covalent kinetic stabilizers synthesized exhibit fluorescence upon conjugation and therefore could have imaging applications as a consequence of the environment sensitive fluorescence of the chromophore.