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

Chemical Properties

yellow crystalline powder

Uses

Different sources of media describe the Uses of 349-96-2 differently. You can refer to the following data:
1. 4-Nitrobenzenesulfonyl Fluoride is a protein modifying agent shown to be specific for tyrosine.
2. Sulfonyl fluoride motif can be used as a connector for the assembly of -SO2- linked small molecules with proteins or nucleic acids. This new click chemistry approach through sulfates is a complimentary approach to using amides and phosphate groups as linkers.

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

Upstream product

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

Downstream Products

• 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 
• 73901-01-6 p-nitrobenzenesulfonyl azide 
• 36195-98-9 (4-Nitro-benzenesulfonylmethylene)-triphenyl-λ⁵-phosphane 
• 98-62-4 4-aminobenzenesulfonyl fluoride 
• 27831-94-3 N-((4-nitrophenyl)sulfonyl)benzamide 

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.).

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.

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.