349-78-0

Usage

Uses

Used in Organic Synthesis:
3-NITROBENZENESULPHONYL FLUORIDE 97 is used as a reagent for the introduction of the nitrobenzenesulfonyl (Nosyl) group in organic synthesis. This group serves as a protective group for amines, which is crucial in various chemical reactions and processes.
Used in Pharmaceutical Industry:
3-NITROBENZENESULPHONYL FLUORIDE 97 is used as a reagent in the synthesis of pharmaceutical compounds. The Nosyl group can be used to protect amines during the synthesis process, ensuring the stability and functionality of the final product.
Used in Research and Development:
3-NITROBENZENESULPHONYL FLUORIDE 97 is used as a research tool in the development of new chemical compounds and processes. Its ability to introduce the Nosyl group makes it a valuable resource for scientists and researchers working in the field of organic chemistry.

InChI:InChI=1/C6H4ClFO2S/c7-11(9,10)6-3-1-5(8)2-4-6/h1-4H

Upstream product

• 368-43-4 phenylsulfonyl fluoride 
• 121-52-8 3-nitrophenylsulfonamide 
• 121-51-7 3-nitrobenzenesulphonyl chloride 
• 15898-46-1 sodium 3-nitrobenzenesulfinate 
• 51516-96-2 3-nitrophenylhydrazine hydrochloride 
• 586-36-7 3-nitrophenyldiazonium tetrafluoroborate 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 2613-26-5 3-nitrophenylsulfur pentafluoride 
• 2557-81-5 pentafluorosulfanylbenzene 
• 127-68-4 sodium 3-nitrobenzenesulfonate 

Downstream Products

• 936091-26-8 N-tert-butyl-3-{5-methyl-2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylamino]-pyrimidin-4-ylamino}-benzenesulfonamide 

Relevant academic research and scientific papers

Design, synthesis, and evaluation of cell permeable probes for protein kinases

We have explored a novel molecular framework with a lysine core to prepare a probe library for protein kinases. Active site-directed probes, identified through screening of the library, displayed desirable labelling properties, including target specificity, good linear response to the corresponding enzymatic activity and cell permeability. Finally, a two-stage protocol utilizing the newly developed probe with an immunoprecipitation step was successfully established to monitor intracellular Src kinase activity in RK3E-v-Src cells.

Copper-catalyzed three-component reaction of arylhydrazine hydrochloride, DABSO, and NFSI for the synthesis of arenesulfonyl fluorides

This paper reports a convenient copper-catalyzed three-component conversion of arylhydrazine hydrochlorides to arenesulfonyl fluorides in good yields under mild conditions, using 1,4-diazabicyclo [2.2.2]octane bis(sulfur dioxide) (DABSO) as a sulfonyl source andN-fluorobenzenesulfonimide (NFSI) as a fluorine source based on a radical sulfur dioxide insertion and fluorination strategy. Notably, arylhydrazine hydrochloride is used as a safe precursor of aryl radicals.

Arenesulfonyl Fluoride Synthesis via Copper-free Sandmeyer-type Fluorosulfonylation of Arenediazonium Salts

The limited availability of highly valuable arenesulfonyl fluorides seriously hinders their further application in many research fields including medicinal chemistry and chemical biological, organic synthesis, polymer preparation, etc. We report herein a mild and efficient copper-free Sandmeyer-type fluorosulfonylation reaction of various arenediazonium salts to prepare valuable arenesulfonyl fluorides using K2S2O5 as both a reductant and a practical sulfonyl source in combination with N-fluorobenzenesulfonimide as an effective fluorine source. This methodology provides an attractive route to diverse important arenesulfonyl fluorides given the overall practicality and scope.

Directed ortho-Metalation of Arenesulfonyl Fluorides and Aryl Fluorosulfates

Studies on directed ortho -metalation (DoM) of arenesulfonyl fluorides (ArSO 2 F) with in situ electrophile trapping are presented. Under optimized conditions (LDA, THF, -78 °C), a series of model substrates was mono- and difunctionalized with trimethylsilyl chloride in good yields. The synthetic results reveal powerful directing character of the SO 2 F group, being ahead of bromine and methoxy substituents. Under the same metalation conditions, aryl fluorosulfates (ArOSO 2 F) display fragmentation to arynes and migration of the SO 2 F group to the ortho position (anionic thia-Fries rearrangement).

Facile one-pot synthesis of sulfonyl fluorides from sulfonates or sulfonic acids

A facile cascade process for directly transforming the abundant and inexpensive sulfonates (or sulfonic acids) to the highly valuable sulfonyl fluorides was developed. This new protocol features mild reaction conditions using readily available and easy-to-operate reagents. A diverse set of sulfonyl fluorides was prepared facilitating the enrichment of the sulfonyl fluoride library.

(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.

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.

Mono- and dinitration of pentafluorosulfanylbenzenes with [NO 2][BF4], and substrate selectivity (PhSF5 vs PhCF3 and PhSF5 vs PhNO2) in competitive nitration

PhSF5 1 reacts with NO2+BF 4-/TfOH in CH2Cl2 (DCM) at room temperature to give 1-nitro-3-(pentafluorosulfanyl)benzene 2 in near quantitative yield. The dinitro derivative 4 is synthesized from 2 by reaction with NO2+BF4-/TfOH at 70 °C. The p-MeC6H4SF5 is mononitrated at room temperature with NO2+BF4-/DCM and dinitrated with NO2+BF4-/TfOH. Substrate selectivity (kPhSF5kRPh) in competitive nitration for PhSF5/PhCF3 and PhSF5/PhNO 2 with NO2+BF4- in DCM at room temperature was determined at 21.3 and ～1 respectively. Relative stability of the corresponding benzenium ions were gauged by DFT from the isodesmic proton transfer reaction SF5-C6H 6+ + R-C6H5 → SF 5-C6H5 + R-C6H6 + (R = CF3 and NO2). These studies indicate that reactivity of ArSF5 in SEAr is similar to ArNO 2.

Herbicidally active phenylsubstituted 5-and 6-membered heterocyclic compounds

A compound of formula (I): STR1 where E is oxygen or sulphur; A is CR3 or N where R3 is hydrogen or hydrocarbyl; D completes a 5 or 6-membered non-aromatic heterocyclic ring which optionally contains additional heteroatoms selected from oxygen, nitrogen or sulphur and which is optionally substituted by an optionally substituted lower hydrocarbyl group, or an optionally substituted heteroaryl group; R1 and R2 are each independently hydrogen; optionally substituted lower hydrocarbyl, or optionally substituted heteroaryl, or R1 and R2 together with the nitrogen atom to which they are attached, form a heterocyclic ring; Z represents halogen optionally substituted lower hydrocarbyl, optionally substituted lower hydocarbyloxy, optionally substituted lower hydrocarbylthio, hydrocarbylsulphinyl or hydrocarbylsulphonyl, cyano, nitro, CHO, NHOH, ONR7' R7", SF5 ; CO (optionally substituted lower hydrocarbyl), acylamino, COOR7, SO2 NR8 R9, CONR10 R11, OR12 or NR13 R14 where R7, R7', R7", R8, R9, R10 and R11 are independently hydrogen or lower hydrocarbyl; R12 is hydrogen; SO2 lower hydrocarbyl or COR15 ; R13 and R14 are independently lower hydrocarbyl, lower hydrocarbyloxy or a group R12 ; R15 is OR16, NR17 R18, hydrogen or lower hydrocarbyl; R16 is lower hydrocarbyl; R17 and R18 are independently hydrogen or lower hydrocarbyl; provided that when there are two or more substituents Z, they may be the same or different; and m is 0 or an integer from 1 to 5.

KINETICS OF THE TRANSFORMATIONS OF AROMATIC SULFO DERIVATIVES TO ACID HALIDES IN CHLORO- AND FLUOROSULFONIC ACID MEDIA

The pseudofirst-order rate constants for the formation of the corresponding sulfonic acid halides (keff) from sulfo derivatives with the general formula RC6H4SO3X, where X = NH2, Cl, F, and R = H, p-Cl, p-NO2, and m-NO2, were measured by GLC in fluorosulfonic and chlorosulfonic acids.The effect of substituents in the benzene ring on the rate of the transformations of the sulfo derivatives into the halides is similar to the previously investigated effect of substituents on the rate of solvolysis of substituted benzenesulfonyl halides in 100percent sulfuric acid (ρ -4).Com parison of the ratios of the keff values for the transformations of the sulfonamides in chlorosulfonic and fluorosulfonic acids and also the sulfonyl fluorides in 100percent sulfuric acid and chlorosulfonic acid with the ratios of the acidities of the respective media shows that these reactions have acid-catalytic character.The sulfonyl chlorides and sulfonamides in 100percent sulfuric acid are solvolyzed to a significant degree with the participation of H2S2O7.