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Sigma-Aldrich

N-Fluorobenzenesulfonimide

97%

Synonym(s):

N-Fluorodi(benzenesulfonyl)amine, N-Fluorodibenzenesulfonimide, NFSI

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About This Item

Linear Formula:
(C6H5SO2)2NF
CAS Number:
133745-75-2
Molecular Weight:
315.34
Beilstein/REAXYS Number:
5348902
MDL number:
MFCD00144885
UNSPSC Code:
12352101
PubChem Substance ID:
24864479
NACRES:
NA.22

assay

97%

form

powder

mp

110 °C (dec.) (lit.)

SMILES string

FN(S(=O)(=O)c1ccccc1)S(=O)(=O)c2ccccc2

InChI

1S/C12H10FNO4S2/c13-14(19(15,16)11-7-3-1-4-8-11)20(17,18)12-9-5-2-6-10-12/h1-10H

InChI key

RLKHFSNWQCZBDC-UHFFFAOYSA-N

Related Categories

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.

Application

Reagent employed in a palladium-catalyzed enantioselective fluorination of t-butoxycarbonyl lactones and lactams. Also used in the electrophilic difluorination of dihalopyridines with butyl lithium and in the direct conversion of alcohols to dibenzenesulfonamides with triphenylphosphine.
Stable, easy-to-handle, crystalline material which readily transfers F+ to enolates and carbanions.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Toshiaki Suzuki et al.
The Journal of organic chemistry, 72(1), 246-250 (2006-12-30)
An efficient catalytic enantioselective fluorination of tert-butoxycarbonyl lactones and lactams is reported. Reactions of the lactone substrates proceeded smoothly in an alcoholic solvent with a catalytic amount of chiral Pd(II) complex. In the case of the less acidic lactam substrates
N-fluorobenzenesulfonimide
Bizet V
Synlett, 23(18), 2719-2720 (2012)
Anthony A Fodor et al.
The Journal of general physiology, 127(6), 755-766 (2006-06-01)
The study of ion channel function is constrained by the availability of structures for only a small number of channels. A commonly used bioinformatics technique is to assert, based on sequence similarity, that a domain within a channel of interest
N-Fluorobenzenesulfonimide
Poss AJ
Encyclopedia of Reagents for Organic Synthesis, Second Edition, 23(18), 2719-2720 (2001)
Tetrahedron Letters, 47, 8457-8457 (2006)
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