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HomeProduct name listN-Fluorobenzenesulfonimide

N-Fluorobenzenesulfonimide

Synonym(s):N-Fluorodi(benzenesulfonyl)amine;N-Fluorodibenzenesulfonimide;NFSI

  • CAS NO.:133745-75-2
  • Empirical Formula: C12H10FNO4S2
  • Molecular Weight: 315.34
  • MDL number: MFCD00144885
  • EINECS: 000-000-0
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-08-22 14:21:17
N-Fluorobenzenesulfonimide Structural

What is N-Fluorobenzenesulfonimide?

Chemical properties

Off-white to light brown crystalline powder

The Uses of N-Fluorobenzenesulfonimide

N-Fluorobenzenesulfonimide fluorinates aromatics, enolates, azaenolates and carbanions in high yield. It is used for diastereoselective fluorination of Li enolates of chiral carboximides, for directed fluorination of ortho-lithiated aromatics and for a review of electrophilic N-F fluorinating agents. Asymmteric fluorinations is effected in the presence of a Pd-BINAP catalyst system at room temperature in an ionic liquid. It is a reagent employed in a palladium-catalyzed enantioselective fluorination of t-butoxycarbonyl lactones and lactams. It is also used in the electrophilic difluorination of dihalopyridines with butyl lithium and in the direct conversion of alcohols to dibenzenesulfonamides with triphenylphosphine.

The Uses of N-Fluorobenzenesulfonimide

Versatile fluorinating reagent used in the fluorination of aryls, enolates, carbanions, organolithiums, etc.

What are the applications of Application

N-Fluorobenzenesulfonimide is a mild electrophilic fluorinating reagent, that can also be used as a strong oxidant for the promotion of reductive elimination from transition metals.

General Description

N-Fluorobenzenesulfonimide (NFSi) is a commonly used electrophilic fluorinating agent in organic synthesis to introduce fluorine into neutral organic molecules. It is also used to fluorinate nucleophilic substrates such as reactive organometallic species and malonate anions.
NFSi can be synthesized by the reaction of benzenesulfonimide with fluorine.

Properties of N-Fluorobenzenesulfonimide

Melting point: 114-116 °C
Boiling point: 471.4±28.0 °C(Predicted)
Density  1.4466 (estimate)
Flash point: 110℃
storage temp.  Keep in dark place,Inert atmosphere,Room temperature
solubility  Very soluble in acetonitrile, dichloromethane or THF and less soluble in toluene.
form  solid
pka -32.45±0.70(Predicted)
color  white
BRN  5348902
CAS DataBase Reference 133745-75-2(CAS DataBase Reference)

Safety information for N-Fluorobenzenesulfonimide

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for N-Fluorobenzenesulfonimide

InChIKey RLKHFSNWQCZBDC-UHFFFAOYSA-N

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