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Published TCIMAIL newest issue No.197

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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

Product Documents:

Size	Unit Price	Belgium	Japan*	Quantity
5G	€42.00	7	≥100
25G	€163.00	2	≥100

*Stock available in Belgium will be delivered in 1 to 3 days
*Stock available in Japan will be delivered in 1 to 2 weeks (excludes regulated items and dry ice shipments).

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General Information plus

Product Number	F0335
Purity / Analysis Method	>98.0%(T)(HPLC)
Molecular Formula / Molecular Weight	C₁₂H₁₀FNO₄S₂ = 315.33
Physical State (20 deg.C)	Solid
Storage Temperature	Room Temperature (Recommended in a cool and dark place, <15°C)
CAS RN	133745-75-2
Reaxys Registry Number	5348902
PubChem Substance ID	87570107
SDBS (AIST Spectral DB)	19601
MDL Number	MFCD00144885

Specifications & Properties plus

Safety & Regulations plus

Applications & Literature plus

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

One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides

A. T. Davies, J. M. Curto, S. W. Bagley, M. C. Willis, Chem. Sci. 2017, 8, 1233.

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

K. Shibatomi, K. Kitahara, T. Okimi, Y. Abe, S. Iwasa, Chem. Sci. 2016, 7, 1388.

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

S. Wang, Z. Ni, X. Huang, J. Wang, Y. Pan, Org. Lett. 2014, 16, 5648.

Application

Synthesis of Stereoseletive 1-Indanone Derivatives

Reference

J. Nie, H.-W. Zhu, H.-F. Cui, M.-Q. Hua, J.-A. Ma, Org. Lett. 2007, 9, 3053.

PubMed Literature

Articles/Brochures

TCIMAIL

[Research Articles] An Enantioselective Fluorination of α-Branched Aldehydes Using Newly Developed Chiral Amine Catalyst
[Research Articles] Copper-catalyzed Direct Amidation of Heterocycles with N-Fluorobenzenesulfonimide
[TCI Practical Example] One-Pot Palladium-Catalyzed Fluorosulfonylation of an Aryl Bromide Using DABSO and NFSI

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Product Categories

Chemistry

Synthetic Reagents

Fluorination Reagents [Synthetic Reagents]

Fluorination [Synthetic Reagents]

Electrophilic Fluorinating Agents

Chemistry

Synthetic Reagents

Fluorination Reagents [Synthetic Reagents]

Fluorination [Synthetic Reagents]

Electrophilic Fluorinating Agents

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

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. P201 : Obtain special instructions before use. P264 : Wash skin thoroughly after handling. P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection/ hearing protection. P308 + P313 : IF exposed or concerned: Get medical advice/ attention. P337 + P313 : If eye irritation persists: Get medical advice/ attention.

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

N-Fluorobenzenesulfonimide [Fluorinating Reagent]

Used Chemicals

Procedure

Experimenter’s Comments

Analytical Data

Lead Reference

References

References

Reference

Articles/Brochures

Safety Data Sheet (SDS)

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C of A & Other Certificates

Sample C of A

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

N-Fluorobenzenesulfonimide [Fluorinating Reagent]

Used Chemicals

Procedure

Experimenter’s Comments

Analytical Data

Lead Reference

References

References

Reference

Articles/Brochures

Safety Data Sheet (SDS)

Specifications

C of A & Other Certificates

Sample C of A

Analytical Charts

Other Documents

Product Categories

Chemistry

Chemistry