145490-75-1

Basic information

• Product Name: N-Fluorobenzenesulfonimide
• Synonyms: N-Fluorobenzenesulphonimide; N-fluorobenzenesulfonamide; 3,4-bis(trifluoromethyl)benzoic acid; NFSI; N-Fluorobenzene sulfonimide; N-Fluorobenzenesulfonmide (NFSI); N-Fluorobenzenesulfonmide(NFSI)
• CAS NO: 145490-75-1
• Molecular Formula: C₆H₆FNO₂S
• Molecular Weight: 258.1173
• Mol File: 145490-75-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: 110-115℃
• Boiling Point: 244.5°C at 760 mmHg
• Flash Point: 101.7°C
• Density: 1.527g/cm³
• Vapor Pressure: 0.0162mmHg at 25°C
• Refractive Index: 1.424
• CAS DataBase Reference: N-Fluorobenzenesulfonimide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Fluorobenzenesulfonimide(145490-75-1)
• EPA Substance Registry System: N-Fluorobenzenesulfonimide(145490-75-1)

Safety Data

• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:
• Safety Statements: S26:; S37/39:
• Hazardous Substances Data: 145490-75-1(Hazardous Substances Data)

Usage

General Description

N-Fluorobenzenesulfonimide, also known as NFSI, is a highly reactive and versatile chemical compound widely used in organic synthesis and fluorination reactions. It is a powerful fluorinating agent that can be used to introduce fluorine atoms into organic molecules, making it an important tool in the production of pharmaceuticals, agrochemicals, and materials science. NFSI is known for its high selectivity and efficiency in fluorination reactions, and its use has been documented in a wide range of applications, including the synthesis of fluorinated compounds for biological studies and the modification of natural products for medicinal purposes. Additionally, NFSI has shown potential as a reagent for the late-stage fluorination of complex molecules, making it a valuable tool for the development of new medicines and materials.

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 
• 908814-02-8 1-phenyl-2-(phenylsulfonyl)ethan-1-one oxime 
• 20605-46-3 3-(benzenesulfonyl)propenylbenzene 
• 26189-62-8 phenyl 2,2-diphenylethenyl sulfone 

Relevant articles and documents

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.

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.