349-96-2

Usage

Uses

Used in Pharmaceutical Industry:
4-Nitrobenzenesulfonyl Fluoride is used as a protein modifying agent for [application reason] the modification of tyrosine residues in proteins. This allows for the study of protein structure, function, and interactions, which is crucial in drug discovery and development.
Used in Chemical Synthesis:
4-Nitrobenzenesulfonyl Fluoride is used as a connector for [application reason] the assembly of -SO2linked small molecules with proteins or nucleic acids. This new click chemistry approach through sulfates is a complimentary method to using amides and phosphate groups as linkers, providing an alternative route for the synthesis of bioconjugates and other complex molecules.
Used in Research and Development:
4-Nitrobenzenesulfonyl Fluoride is used as a research tool for [application reason] the investigation of protein tyrosine phosphorylation, which plays a significant role in various cellular processes, including signal transduction, cell adhesion, and cell migration. Understanding these processes is essential for the development of targeted therapies for various diseases.
Used in Diagnostics:
4-Nitrobenzenesulfonyl Fluoride can be used as a diagnostic agent for [application reason] the detection and quantification of tyrosine phosphorylation events in biological samples. This can aid in the identification of disease biomarkers and the monitoring of treatment responses in various clinical settings.

InChI:InChI=1/C6H4FNO4S/c7-13(11,12)6-3-1-5(2-4-6)8(9)10/h1-4H

Upstream product

• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 937-32-6 4-nitrobenzenesulfenyl chloride 
• 75-09-2 dichloromethane 
• 100-32-3 di(p-nitrophenyl) disulfide 
• 2937-05-5 4-nitrobenzenesulfonohydrazide 
• 15959-31-6 sodium 4-nitrobenzenesulfinate 
• 100-01-6 4-nitro-aniline 
• 88683-47-0 2-((4-nitrophenyl)thio)isoindoline-1,3-dione 
• 456-27-9 4-nitrobenzenediazonium tetrafluoroborate 
• 636-99-7 4-nitrophenylhydrazine hydrochloride 

Downstream Products

• 98-62-4 4-aminobenzenesulfonyl fluoride 
• 30904-42-8 p-nitrobenzenesulfonate anion 
• 1254832-49-9 1-(chloro(phenylsulfonyl)methylsulfonyl)-4-nitrobenzene 
• 1254832-45-5 1-(methoxy(phenylsulfonyl)methylsulfonyl)-4-nitrobenzene 
• 1254832-41-1 1-(fluoro(phenylsulfonyl)methylsulfonyl)-4-nitrobenzene 
• 6325-93-5 p-nitrobenzenesulfonamide 
• 1418939-11-3 C₁₀H₇F₉N₂O₄S₂ 
• 1418939-13-5 C₁₆H₁₄F₈N₄O₈S₄ 
• 1418939-15-7 C₁₈H₁₄F₁₂N₄O₈S₄ 
• 1418939-17-9 C₁₁H₈F₁₁N₃O₈S₄ 
• 1418939-19-1 C₁₃H₈F₁₅N₃O₈S₄ 
• 798571-94-5 C₇H₄F₃N₃O₄S₂ 
• 1418939-22-6 C₁₀H₄F₉N₃O₄S₂ 
• 1418939-24-8 C₁₆H₈F₈N₆O₈S₄ 

Relevant academic research and scientific papers

Visible-Light-Mediated Synthesis of Sulfonyl Fluorides from Arylazo Sulfones

Sulfonyl fluorides are useful motifs for a wide range of applications in organic synthesis including sulfur (VI) fluoride exchange-based “click chemistry.” Herein, a visible-light-mediated synthesis of sulfonyl fluorides from arylazo sulfones is described. In the present study, K2S2O5 and N-fluorobenzenesulfonimide (NFSI) were used as the sulfonyl source and fluorinating agent, respectively, for visible-light-mediated fluorosulfonylation of arylazo sulfones to prepare various sulfonyl fluorides in 60–85% yield. This protocol is a synthetic approach to provide useful sulfonyl fluoride structures at room temperature. (Figure presented.).

Metal-Free Visible-Light Synthesis of Arylsulfonyl Fluorides: Scope and Mechanism

The first metal-free procedure for the synthesis of arylsulfonyl fluorides is reported. Under organo-photoredox conditions, aryl diazonium salts react with a readily available SO2 source (DABSO) to afford the desired product through simple nucleophilic fluorination. The reaction tolerates the presence of both electron-rich and -poor aryls and demonstrated a broad functional group tolerance. To shed the light on the reaction mechanism, several experimental techniques were combined, including fluorescence, NMR, and EPR spectroscopy as well as DFT calculations.

SuFExable Isocyanides for Ugi Reaction: Synthesis of Sulfonyl Fluoro Peptides

Herein, the sulfonyl fluoro isocyanides were first developed as a new type of SuFExable synthon, and they are used as building blocks in the Ugi reaction (U-4CR). The Ugi reaction was established and the substrate scope was investigated, and various sulfonyl fluoro α-amino amides and peptides could be reached in a one-step synthesis. Therefore, this protocol opens a new vision for SuFExable building blocks and click chemistry, and it also provides a distinct approach to sulfonyl fluoro peptides.

Desulfonative Suzuki–Miyaura Coupling of Sulfonyl Fluorides

Sulfonyl fluorides have emerged as powerful “click” electrophiles to access sulfonylated derivatives. Yet, they are relatively inert towards C?C bond forming transformations, notably under transition-metal catalysis. Here, we describe conditions under which aryl sulfonyl fluorides act as electrophiles for the Pd-catalyzed Suzuki–Miyaura cross-coupling. This desulfonative cross-coupling occurs selectively in the absence of base and, unusually, even in the presence of strong acids. Divergent one-step syntheses of two analogues of bioactive compounds showcase the expanded reactivity of sulfonyl fluorides to encompass both S?Nu and C?C bond formation. Mechanistic experiments and DFT calculations suggest oxidative addition occurs at the C?S bond followed by desulfonation to form a Pd-F intermediate that facilitates transmetalation.

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.

Method for preparing aryl sulfonyl fluoride by using aryl hydrazine hydrochloride as raw material

The invention relates to a method for preparing aryl sulfonyl fluoride by using aryl hydrazine hydrochloride as a raw material. According to the method, aryl sulfonyl fluoride is synthesized by taking the aryl hydrazine hydrochloride as a raw material and adding a sulfur dioxide source and a fluorination reagent under the conditions of copper salt catalysis and alkali promotion through a strategy of insertion and fluorination of free radical sulfur dioxide. Compared with the prior art, the aryl sulfonyl fluoride is synthesized under the oxidation condition, and the influence of air on the reaction is not obvious in an experiment; and the reaction synthesis method is simple, good in selectivity, excellent in yield, mild in reaction condition, short in reaction time and universal to various aryl hydrazine hydrochloride substrates, and the method provides a new thought for synthesis of aryl sulfonyl fluoride.

Large-Scale Practical Synthesis of Boc-Protected 4-Fluoro-l-Proline

A large-scale synthesis process of N-Boc-4-fluoro-l-proline (1) from N-Boc-4-hydroxy-l-proline methyl ester (2) using nosyl fluoride (13) as a deoxyfluorinating agent has been developed. An eco-friendly and large-scale feasible process using a single solvent was developed to afford moderate yields of products with excellent purity >99% by high-performance liquid chromatography. The key feature of the optimization involving chromatography-free purification and isolation on a kilogram-scale at a pilot plant scale is described.

A Unified Strategy for Arylsulfur(VI) Fluorides from Aryl Halides: Access to Ar-SOF3 Compounds

A convenient protocol to selectively access various arylsulfur(VI) fluorides from commercially available aryl halides in a divergent fashion is presented. Firstly, a novel sulfenylation reaction with the electrophilic N-(chlorothio)phthalimide (Cl-S-Phth) and arylzinc reagents afforded the corresponding Ar-S-Phth compounds. Subsequently, the S(II) atom was selectively oxidized to distinct fluorinated sulfur(VI) compounds under mild conditions. Slight modifications on the oxidation protocol permit the chemoselective installation of 1, 3, or 4 fluorine atoms at the S(VI) center, affording the corresponding Ar-SO2F, Ar-SOF3, and Ar-SF4Cl. Of notice, this strategy enables the effective introduction of the rare and underexplored -SOF3 moiety into various (hetero)aryl groups. Reactivity studies demonstrate that such elusive Ar-SOF3 can be utilized as a linchpin for the synthesis of highly coveted aryl sulfonimidoyl fluorides (Ar-SO(NR)F).

Copper-free Sandmeyer-type Reaction for the Synthesis of Sulfonyl Fluorides

A copper-free Sandmeyer-type fluorosulfonylation reaction is reported. Utilizing Na2S2O5 and Selectfluor as the sulfur dioxide and fluorine sources, respectively, aryldiazonium salts were transformed into sulfonyl fluorides. The one-pot direct synthesis of sulfonyl fluorides from aromatic amines was also realized via in situ diazotization. The practicality of this method was demonstrated by the broad functional group tolerance, gram-scale synthesis, and late-stage fluorosulfonylation of natural products and pharmaceuticals.

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.