N-Fluorobenzenesulfonimide

N-Fluorobenzenesulfonimide Basic information
Product Name:N-Fluorobenzenesulfonimide
Synonyms:NFSI;N-FLUOROBENZENESULFONAMIDE;N-FLUOROBENZENESULFONIMIDE;N-FLUOROBENZENESULPHONIMIDE;N-FLUOROBIS(PHENYLSULFONYL)AMINE;N-FLUORODIBENZENESULFONAMIDE;N-Fluorobenzenesulfonimide(NFSI);N-FluorobenzenesulfonMide (NFA)
CAS:133745-75-2
MF:C12H10FNO4S2
MW:315.34
EINECS:000-000-0
Product Categories:kl;Synthetic Organic Chemistry;Electrophilic Fluorinating Reagents;Fluorinating Reagents;Fluorinating Reagents & Building Blocks for Fluorinated Biochemical Compounds;alkyl Fluorine;Fluorination;Halogenation
Mol File:133745-75-2.mol
N-Fluorobenzenesulfonimide Structure
N-Fluorobenzenesulfonimide Chemical Properties
Melting point 114-116 °C
Boiling point 471.4±28.0 °C(Predicted)
density 1.4466 (estimate)
Fp 110℃
storage temp. Keep in dark place,Inert atmosphere,Room temperature
solubility Very soluble in acetonitrile, dichloromethane or THF and less soluble in toluene.
pka-32.45±0.70(Predicted)
form solid
color white
BRN 5348902
InChIKeyRLKHFSNWQCZBDC-UHFFFAOYSA-N
CAS DataBase Reference133745-75-2(CAS DataBase Reference)
Safety Information
Hazard Codes Xi,O
Risk Statements 36/37/38
Safety Statements 26-37/39
WGK Germany 3
10
Hazard Note Oxidising Agent
TSCA No
HazardClass IRRITANT
HS Code 29242990
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
ALFA English
N-Fluorobenzenesulfonimide Usage And Synthesis
Chemical PropertiesOff-white to light brown crystalline powder
UsesVersatile fluorinating reagent used in the fluorination of aryls, enolates, carbanions, organolithiums, etc.
UsesN-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.
ApplicationN-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 DescriptionN-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.
N-Fluorobenzenesulfonimide Preparation Products And Raw materials
Preparation Products1-Bromo-4-(phenylsulfonyl)benzene-->3-FLUOROPHENYL ISOTHIOCYANATE-->Benzenesulfonylazide-->Sulfenone-->1-(PHENYLSULFONYL)-1H-BENZOTRIAZOLE
4-Bromo-2,6-difluorobenzoic acid 3,4,5-Trifluorophenylacetic acid 2,4-Dichloro-5-fluoropyrimidine 4-BROMO-2,6-DIFLUOROBENZYL BROMIDE 2,3-Difluoro-4-ethoxybenzeneboronic acid Dibenzenesulfonimide Sulfamide Novaluron N-Fluorobenzenesulfonimide Benzenesulfonamide N-Ethylmethylamine TRIFLUOROMETHANESULFONAMIDE Dibenzylamine Triethylamine Sulfanilamide Bis(2-ethylhexyl)amine p-Toluenesulfonamide Triethanolamine

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