349-96-2

Basic information

• Product Name: 4-NITROBENZENESULFONYL FLUORIDE
• Synonyms: 4-Nitrobenzenesulfonyl fluoride,99%;4-Nitrobenzenesulfonyl fluoride, 99% 5GR;4-Nitrobenzene-1-sulfonyl fluoride;Benzenesulfonylfluoride, 4-nitro-;4-NITROBENZENESULFONYL FLUORIDE;4-NITROBENZENESULFONYL FLUORIDE 99%
• CAS NO: 349-96-2
• Molecular Formula: C₆H₄FNO₄S
• Molecular Weight: 205.16
• Product Categories: Protection & Derivatization Reagents (for Synthesis);Synthetic Organic Chemistry
• Mol File: 349-96-2.mol
• Article Data: 20

Chemical Properties

• Melting Point: 76-80 °C
• Boiling Point: 305.1 °C at 760 mmHg
• Flash Point: 138.3 °C
• Appearance: Yellow/Crystalline Powder
• Density: 1.5663 (estimate)
• Vapor Pressure: 0.00151mmHg at 25°C
• Refractive Index: 1.544
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 4-NITROBENZENESULFONYL FLUORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-NITROBENZENESULFONYL FLUORIDE(349-96-2)
• EPA Substance Registry System: 4-NITROBENZENESULFONYL FLUORIDE(349-96-2)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 45-36/37/39-26-27
• RIDADR: 1759
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 349-96-2(Hazardous Substances Data)

Usage

Description

4-Nitrobenzenesulfonyl Fluoride, also known as 4-NBSF, is a chemical compound with the formula C6H4FNO4S. It is a yellow crystalline powder that is primarily used as a protein modifying agent. It is known for its specificity towards tyrosine, making it a valuable tool in various applications.

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 
• 36195-98-9 (4-Nitro-benzenesulfonylmethylene)-triphenyl-λ⁵-phosphane 
• 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 

Relevant articles and documents

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.).

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.

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.