N-Fluorobenzenesulfonimide(cas no.: 133745-75-2 )

Product manager: Selina Zhang; Email: selina@coreychem.com

N-Fluorobenzenesulfonimide (NFSI, CAS 133745-75-2) is an important organic synthesis reagent. Its main roles and applications are as follows:

Primary Functions

1. Electrophilic Fluorinating Agent:

   • Core Use: Acts as a mild electrophilic fluorine source, capable of introducing fluorine atoms into electron-rich substrates (such as enol silyl ethers, enamines, aromatic rings, carbanions, etc.) under neutral or weakly basic conditions.

   • Features: Mild reaction conditions, good selectivity, fewer side reactions, and safer and easier to handle compared to traditional fluorinating agents (e.g., F₂, XeF₂).

2. Fluorine Transfer via the N–F Bond:

   • Its relatively weak N–F bond allows it to generate fluorine radicals under radical initiators (e.g., light, heat, or redox catalysts), enabling radical fluorination reactions.

Specific Application Areas

1. Pharmaceutical and Agrochemical Synthesis:

   • Used in the synthesis of fluorinated drug intermediates, as fluorine atoms can significantly alter a molecule’s biological activity, metabolic stability, and lipophilicity. Examples include fluorine-containing structures common in anticancer, antiviral, and central nervous system drugs.

   • Introducing fluorine atoms into pesticide molecules can enhance their biological activity and selectivity.

2. Materials Science:

   • Synthesis of fluorinated functional materials (e.g., fluorinated liquid crystals, polymeric materials) to improve stability, hydrophobicity, or optical properties.

3. Organic Methodology Research:

   • Serves as a fluorine chemistry tool reagent for developing new fluorination reactions (e.g., asymmetric fluorination, direct C–H bond fluorination).

Advantages and Precautions

• Advantages:

  • Solid crystalline form, easy to store and weigh;

  • Relatively stable to air and moisture, convenient to handle;

  • Reaction by-products are benzenesulfonimide derivatives, typically easy to separate.

• Precautions:

  • Still possesses certain oxidizing properties and toxicity; should be handled in a fume hood, avoiding skin contact;

  • Store away from light and moisture.

Typical Reaction Examples

• Fluorination of Enol Silyl Ethers: Produces α-fluorinated carbonyl compounds.

• Fluorination of Aromatic Rings: Electrophilic fluorination of electron-rich aromatic rings catalyzed by Lewis acids.

• Radical Fluorination: Selective fluorination of alkane C–H bonds under light or radical initiators.

Summary

NFSI is an efficient and versatile fluorinating reagent in modern organic fluorine chemistry, widely used in drug development, materials science, and methodology research. It is a key tool for introducing fluorine atoms to modulate molecular properties.

Contact us for more information: selina@coreychem.com