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133745-75-2 - N-Fluorobenzenesulfonimide, 97% - AccuFluor NFSi - N-Fluorobis(phenylsulfonyl)amine - L13955 - Alfa Aesar

L13955 N-Fluorobenzenesulfonimide, 97%

CAS Number
133745-75-2
Synonyms
AccuFluor NFSi
N-Fluorobis(phenylsulfonyl)amine

Size Price ($) Quantity Availability
1g 20.61
5g 67.41
25g 230.40
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N-Fluorobenzenesulfonimide, 97%

MDL
MFCD00144885
EINECS
000-000-0

Chemical Properties

Formula
C12H10FNO4S2
Formula Weight
315.34
Melting point
114-118°
Solubility
Very soluble in acetonitrile, dichloromethane or THF and less soluble in toluene.

Applications

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.

Notes

Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Incompatible with oxidizing agents.

Literature References

Anthony A Fodor.; Richard W Aldrich. Statistical limits to the identification of ion channel domains by sequence similarity. Journal of General Physiology. 2006, 127 (6), 755-766.

Paul A. Sibbald.; Forrest E. Michael. Palladium-Catalyzed Diamination of Unactivated Alkenes Using N-Fluorobenzenesulfonimide as Source of Electrophilic Nitrogen. Org. Lett. 2009, 11 (5), 1147-1149.

Stable, non-hygroscopic, glass-compatible mild electrophilic fluorinating agent, very soluble in acetonitrile, dichloromethane or THF, less soluble in toluene. Fluorinates aromatics, enolates, azaenolates and carbanions in high yield: Synlett, 187, 395 (1991); Tetrahedron Lett., 32, 1631 (1991); for diastereoselective fluorination of Li enolates of chiral carboximides, see: Tetrahedron Lett., 33, 1153 (1992). Asymmteric fluorinations have been effected in the presence of a Pd-BINAP catalyst system at room temperature in an ionic liquid: Org. Lett., 5, 3225 (2003).

For directed fluorination of ortho-lithiated aromatics, see: Tetrahedron Lett., 35, 3465 (1994); ɑɑ-difluorination of benzylic phosphonate anions: Tetrahedron, 54, 1691 (1998); andof benzylic nitriles, tetrazoles and sulfonates: J. Org. Chem., 63, 8052 (1998).

For a review of electrophilic N-F fluorinating agents, see: Chem. Rev., 96, 1737 (1996).

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P280-P305+P351+P338-P304+P340-P362-P312-P321-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Specific treatment (see label). Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
5348902
Harmonized Tariff Code
2935.00
TSCA
No

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