7552-55-8

Usage

Uses

Used in Chemical Synthesis:
1,3-Benzenedisulfonyl difluoride is used as a synthetic intermediate for the assembly of -SO2linked small molecules with proteins or nucleic acids. Its sulfonyl fluoride motif allows for the formation of stable and functional linkages, making it a valuable component in the development of new chemical entities.
Used in Click Chemistry:
1,3-Benzenedisulfonyl difluoride is used as a connector in click chemistry approaches through sulfates. This method complements the use of amides and phosphate groups as linkers, providing an alternative route for the synthesis of complex molecules and bioconjugates.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1,3-benzenedisulfonyl difluoride is used as a building block for the development of novel drugs. Its ability to form stable linkages with biologically relevant molecules makes it a promising candidate for the creation of new therapeutic agents.
Used in Materials Science:
1,3-Benzenedisulfonyl difluoride can be utilized in the development of advanced materials, such as polymers and composites, due to its unique chemical properties. Its incorporation into these materials can lead to enhanced performance characteristics, such as improved mechanical strength or chemical stability.

Upstream product

• 585-47-7 benzene-1,3-disulfonyl chloride 
• 2489-52-3 3-(fluorosulfonyl)benzenesulfonyl chloride 
• 7789-21-1 fluorosulphonic acid 
• 831-59-4 1,3-benzenedisulfonic acid disodium salt 

Downstream Products

• 357-43-7 1,3-bis((trifluoromethyl)sulfonyl)benzene 

Relevant academic research and scientific papers

Sulfur–Fluoride Exchange (SuFEx)-Mediated Synthesis of Sterically Hindered and Electron-Deficient Secondary and Tertiary Amides via Acyl Fluoride Intermediates

Amide bond formation is one of the most executed reactions in chemistry and biology. This is largely due to the ubiquity of the amide functional group in biological molecules, natural products and pharmaceutically important drugs. We report here the development of “SuFExAmide”: a new sulfur–fluoride exchange (SuFEx) click chemistry based protocol for the efficient amidation of carboxylic acids via acyl fluoride intermediates. We have developed benzene-1,3-disulfonyl fluoride as a cost effective, powerful and versatile coupling agent, which delivers challenging secondary and tertiary amides in excellent yields from sterically hindered and electron-deficient amines. The straightforward method offers significant benefits over existing protocols in terms of substrate scope, efficiency and ease of operation and is demonstrated by the synthesis of 44 amides, including GNF6702, an antiprotozoal drug candidate. In the majority of cases, the amide products are obtained in high yield without the need for excess reagents or chromatographic purification.

General and Highly Efficient Syntheses of m-Fluoro Arenes Using Potassium Fluoride-Exchange Method

Tetraphenylphosphonium bromide was found to be a suitable catalyst for the reaction of m-nitroaryl derivatives carrying cyano, nitro, chlorocarbonyl, trifluoromethyl, and chlorosulfonyl groups with potassium fluoride in the presence of a stoichiometric amount of phthaloyl dichloride, giving the corresponding m-fluoro aromatic derivatives in good yields.The catalyst was also found to be efficient for the fluorodesulfonylation of m-(fluorosulfonyl)aryl derivatives to afford m-fluoro arenes by the use of a reaction-distillation technique.

Process for the preparation of fluorinated benzene sulfonyl fluorides

The present invention relates to a process for the preparation of a fluorinated benzene sulfonyl fluoride comprising the step of: heating a benzene sulfonyl fluoride of the Formula (I) STR1 where Y is fluorine, chlorine, bromine, iodine, a methyl group, an ethyl group, or a propyl group; p is 0 to 3; and q is 2 to 6, in the presence of an alkali metal fluoride under conditions and for a time sufficient to provide a fluorinated benzene sulfonyl fluoride of the Formula (II) STR2 where x is 1 to 5; m=q-x; and Y and p are as defined above. The present invention also provides novel benzene sulfonyl fluorides of the Formula (III) STR3 where each Y is meta or para to --SO2 F and is independently selected from the group consisting of chlorine, fluorine, fluorosulfonyl, methyl group, ethyl group, and propyl group; and p is 1 or 2. The fluorinated benzene sulfonyl fluorides are versatile fluorinated intermediates. They are readily converted to sulfonamides of potential activity, or the sulfonyl group can be converted into another functional group, or removed to provide fluorinated benzenes.