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CAS RN: 133745-75-2 | Product Number: F0335

N-Fluorobenzenesulfonimide [Fluorinating Reagent]


Purity: >98.0%(T)(HPLC)
Synonyms:
  • N-Fluorobis(phenylsulfonyl)amine
  • NFSI
  • NFBS
Documents:
5G
$77.00
6   3   ≥40 
25G
$267.00
4   1   ≥40 

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Product Number F0335
Purity / Analysis Method >98.0%(T)(HPLC)
Molecular Formula / Molecular Weight C__1__2H__1__0FNO__4S__2 = 315.33 
Physical State (20 deg.C) Solid
CAS RN 133745-75-2
Reaxys Registry Number 5348902
PubChem Substance ID 87570107
SDBS (AIST Spectral DB) 19601
MDL Number

MFCD00144885

Specifications
Appearance White to Light yellow powder to crystal
Purity(HPLC) min. 98.0 area%
Purity(Iodometric Titration) min. 98.0 %
Melting point 115.0 to 119.0 °C
Properties (reference)
Melting Point 115 °C
GHS
Pictogram Pictogram Pictogram
Signal Word Warning
Hazard Statements H315 : Causes skin irritation.
H319 : Causes serious eye irritation.
H341 : Suspected of causing genetic defects.
Precautionary Statements P501 : Dispose of contents/ container to an approved waste disposal plant.
P202 : Do not handle until all safety precautions have been read and understood.
P201 : Obtain special instructions before use.
P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection.
P308 + P313 : IF exposed or concerned: Get medical advice/ attention.
P337 + P313 : If eye irritation persists: Get medical advice/ attention.
P305 + P351 + P338 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P302 + P352 : IF ON SKIN: Wash with plenty of soap and water.
P332 + P313 : If skin irritation occurs: Get medical advice/ attention.
P362 : Take off contaminated clothing and wash before reuse.
P405 : Store locked up.
Related Laws:
Transport Information:
HS Number 2935.90.9500
Application
TCI Practical Example: One-Pot Palladium-Catalyzed Fluorosulfonylation of an Aryl Bromide Using DABSO and NFSI

パラジウム触媒によるDABSOとNFSIを用いたアリールブロミドのワンポットフッ化スルホニル化

Used Chemicals

Procedure

To a solution of 4-bromobiphenyl (1.17 g, 5.00 mmol), DABSO (721 mg, 3.00 mmol), and PdCl2(Amphos)2 (177 mg, 0.25 mmol) in anhydrous isopropyl alcohol (20 mL) was added triethylamine (2.1 mL, 15 mmol) at room temperature and the mixture was stirred at 75 °C for 23 hours. The suspension was cooled at room temperature and NFSI (2.36 g, 7.5 mmol) was added and the reaction mixture stirred for 3 hours until completion. The solvent was removed under reduced pressure. The residue was diluted with ethyl acetate (20 mL) and filtrated through celite pad. The filtrate was washed with saturated aqueous Na2S2O3 solution (20 mL) and brine (20 mL), dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by medium pressure preparative chromatography (ethyl acetate:hexane = 2:98 - 5:95 on silica gel) to give compound 1 as a white solid (928 mg, 79%).

Experimenter’s Comments

The reaction mixture was monitored by TLC (ethyl acetate:hexane = 1:9, Rf = 0.57) and UPLC-MS.

Analytical Data

Compound 1

1H NMR (400 MHz, CDCl3); δ 8.12–8.04 (m, 2H), 7.86–7.80 (m, 2H), 7.67–7.58 (m, 2H), 7.44-7.55 (m, 3H).

Lead Reference


Application
An Enantioselective Fluorination of α-Branched Aldehydes Using Newly Developed Chiral Amine Catalyst

E1267, F0335

Typical Procedure (synthesis of 2-fluoro alcohol; Ar=Ph, R1=CH3):
To a solution of the chiral amine catalyst [E1267] (20 mg, 0.026 mmol, 10 mol%) in toluene (0.54 mL) is added 3,5-dinitrobenzoic acid (5.5 mg, 0.026 mmol, 10 mol%), 2-phenylpropionaldehyde (52 mg, 0.39 mmol, 1.5 eq.), and N-fluorobenzenesulfonimide (NFSI) (0.26 mmol, 82 mg, 1 eq.) at 0 °C. The reaction mixture is stirred at 0 °C for 48 h, then poured into CH3OH/CH2Cl2 (1:4, 1.3 mL) at 0 °C. To this solution, NaBH4 (1.6 mmol, 6 eq.) is added, and the mixture is stirred at room temperature for 1 h. The reaction is quenched with saturated aq.NH4Cl, and the mixture is extracted with Et2O. The organic layer is dried over Na2SO4, and concentrated. The residue is purified by silica gel chromatography (eluent: hexane/ethyl acetate = 3/1) to give (S)-2-fluoro-2-phenylpropan-1-ol (34.5 mg, 86% yield based on NFSI, 95% ee) as a white solid.

References


Application
Copper-catalyzed Direct Amidation of Heterocycles with N-Fluorobenzenesulfonimide

F0335

Typical Procedure:
In a dry 25 mL round-bottom flask, thiophene (0.5 mmol, 1 eq.), NFSI (0.6 mmol, 1.2 eq.) and CuI (5 mol%) are dissolved in DCE (3 mL), the resulting mixture is put into a preheated oil bath (60 °C) for 8 h. The solution is then cooled to room temperature, evaporated under reduced pressure, diluted with ethyl acetate, washed with a saturated aqueous solution of NaCl, dried over Na2SO4, filtered and evaporated under reduced pressure. The crude product is purified by silica gel column chromatography to afford the corresponding product (166.7 mg, Y. 88 %).

References


Application
Synthesis of Stereoseletive 1-Indanone Derivatives

Reference


PubMed Literature


Documents (Note: Some products will not have analytical charts available.)
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