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

L13955 N-Fluorobenzenesulfonimide, 97%

Codice CAS
133745-75-2
Sinonimi
AccuFluor NFSi
N-Fluorobis(phenylsulfonyl)amine

Dimensioni Prezzo ($) Quantità Disponibilità
1g 23,40
5g 70,20
25g 251,00
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N-Fluorobenzenesulfonimide, 97%

MDL
MFCD00144885
EINECS
000-000-0

Proprietà chimiche

Formula
C12H10FNO4S2
Peso formula
315.34
Punto di fusione
114-118°
Solubilità
Very soluble in acetonitrile, dichloromethane or THF and less soluble in toluene.

Applicazioni

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.

Note

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

Letteratura

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).

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H315-H319-H335

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

Dichiarazioni precauzionali: P260-P201-P280g-P304+P340-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Obtain special instructions before use. Wear protective gloves. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Beilstein
5348902
Codice tariffe armonizzato
2935.90
TSCA
No

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