145490-75-1

Usage

Uses

Used in Pharmaceutical Industry:
N-Fluorobenzenesulfonimide is used as a fluorinating agent for the synthesis of fluorinated compounds, which are essential in the development of new pharmaceuticals. The introduction of fluorine atoms can significantly alter the pharmacokinetic and pharmacodynamic properties of drug molecules, enhancing their efficacy and selectivity.
Used in Agrochemical Industry:
NFSI is utilized as a key reagent in the production of agrochemicals, where fluorinated compounds are often required for their unique properties, such as increased stability and bioactivity. The use of NFSI in this industry contributes to the development of more effective and environmentally friendly pesticides and herbicides.
Used in Materials Science:
N-Fluorobenzenesulfonimide is employed as a fluorinating agent in the synthesis of fluorinated materials with specific properties, such as high thermal stability, chemical resistance, and unique electronic properties. These materials find applications in various fields, including electronics, coatings, and advanced materials for energy storage and conversion.
Used in Biological Studies:
NFSI is used as a reagent for the synthesis of fluorinated compounds for biological research. The introduction of fluorine atoms can provide valuable insights into the structure-activity relationships of biologically active molecules, aiding in the discovery of new drug candidates and the understanding of molecular mechanisms.
Used in Late-Stage Fluorination:
N-Fluorobenzenesulfonimide is used as a reagent for the late-stage fluorination of complex molecules, allowing for the selective introduction of fluorine atoms into specific positions within the molecule. This capability is particularly valuable in the development of new medicines, where late-stage modifications can significantly impact the drug's properties and therapeutic potential.

Upstream product

• 133745-75-2 N-fluorobis(benzenesulfon)imide 
• 98-10-2 benzenesulfonamide 

Downstream Products

• 778595-92-9 1-phenyl-2-fluoro-1,2-dicarba-closo-dodecaborane 
• 1638287-55-4 4-NO₂-NFSI 
• 1638287-56-5 2-F-NFSI 
• 1638287-57-6 3-F-NFSI 
• 1638287-58-7 2-Me-NFSI 
• 325780-05-0 N-(3,4-dimethylphenyl)benzenesulfonamide 
• 13053-76-4 N-(thiophen-2-yl)benzenesulfonamide 
• 7504-85-0 N-(naphthalen-2-yl)benzenesulfonamide 
• 1678-25-7 N-phenylbenzenesulfonamide 
• 6311-65-5 N-p-tolyl-benzenesulfonamide 
• 93729-09-0 N-([1,1’-biphenyl]-2-yl)benzenesulfonamide 
• 21226-31-3 N-(2-bromophenyl)-S-phenylsulfonamide 
• 13587-57-0 N-m-tolyl-benzenesulfonamide 

Relevant academic research and scientific papers

NFSI/KF mediated mild and chemoselective interconversion of aryl TBDMS ethers to their benzene sulfonate

A one pot protocol for the transformation of aryl TBDMS ethers to corresponding benzene sulfonate esters using NFSI (N-flurobenzenesulfonimide)/KF is described. In situ generation of benzenesulfonyl fluoride directs chemoselective cleavage of aryl silyl ethers over alkyl silyl ethers. Electron withdrawing substituent's on aryl ring provided better yield than donating groups. Protecting groups and sensitive functionalities are well tolerated in this methodology. Thus, commercially available inexpensive reagents, mild reaction conditions and step economy are the advantages of this method.

A reagent chloride nitrogen chlorine

The invention relates to a nitrogen-chorine type chlorination agent, and belongs to the field of chlorination agent synthesis. The nitrogen-chorine type chlorination agent is obtained by taking benzene sulfonamide as a substrate, introducing fluorine gas and chlorine gas to react. In the synthesis process, a commercial product is taken as a raw material, the operation is simple, the separation is easy and the yield is high. When chlorination reaction is performed, the conditions are mild, the yield is high and the reaction substrate applied range is wide. Especially, the nitrogen-chorine type chlorination agent has good chlorination activity to dicarbonyl compounds, indole compounds and nitrogen-containing heterocyclic ring compounds.

Nucleophilic reactivity towards electrophilic fluorinating agents: Reaction with N-fluorobenzenesulfonimide ((PhSO2)2NF)

Second-order rate constants for the reaction of N-fluorobenzenesulfonimide (FBS) with nucleophilic reagents, kNu (M-1 s-1), have been measured in aqueous solution at 25°C. Analysis of the reaction products shows that soft polarizable nucleophiles (I-, SCN-, Br-) react at fluorine, whereas hard nucleophiles (oxygen and nitrogen nucleophiles) react at sulfur. The ambident behaviour of this electrophile seems to be related to the relative contribution of electrostatic and orbital interactions in reaching the transition state. The preferential reaction of soft nucleophiles at fluorine and the correlation of kNu values with the one-electron oxidation potentials of the nucleophiles in water suggest that nucleophilic reactivity at fluorine is largely determined by the ease of one-electron transfer from the nucleophile to the electrophile. Nucleophilic addition to fluorine is far more sensitive to the nature of the attacking nucleophile than the corresponding reactions at both saturated (n scale) and unsaturated carbon (N+ scale). Comparison of the rate constants for the reaction of nucleophiles at the sulfonyl group with those for reaction of the same nucleophiles with 2,4-dinitrophenyl acetate reveals a similar reactivity pattern for sulfonyl sulfur and carbonyl carbon as electrophilic centres.