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

L13955 N-Fluorobenzenesulfonimide, 97%

Numéro CAS
133745-75-2
Synonymes
AccuFluor NFSi
N-Fluorobis(phenylsulfonyl)amine

Dimensions Prix ($) Quantité Disponibilité
1g 20,61
5g 67,41
25g 230,40
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N-Fluorobenzenesulfonimide, 97%

MDL
MFCD00144885
EINECS
000-000-0

Propriétés chimiques

Formule
C12H10FNO4S2
Poids formulaire
315.34
Point de fusion
114-118°
Solubilité
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.

Références bibliographiques

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).

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H315-H319-H335

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

Mentions de prudence: 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.

Autres références

Beilstein
5348902
Code tarifaire harmonisé
2935.00
TSCA
No

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