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Thermo Scientific Chemicals
N-Fluorobenzenesulfonimide, 97%
CAS: 133745-75-2 | C12H10FNO4S2 | 315.333 g/mol
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Chemical Identifiers
CAS133745-75-2
IUPAC NameN-(benzenesulfonyl)-N-fluorobenzenesulfonamide
Molecular FormulaC12H10FNO4S2
InChI KeyRLKHFSNWQCZBDC-UHFFFAOYSA-N
SMILESFN(S(=O)(=O)C1=CC=CC=C1)S(=O)(=O)C1=CC=CC=C1
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Specifications
Specification Sheet
Specification SheetAppearance (Color)White to cream to gray
Assay (HPLC)≥96.0%
Melting Point (clear melt)111.0-122.0?C (UK Sourced Material)
FormCrystals or powder or crystalline powder or fused solid
CommentMaterial Sourced in UK and US
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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.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
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.
Solubility
Very soluble in acetonitrile, dichloromethane or THF and less soluble in toluene.
Notes
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Incompatible with oxidizing agents.
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.
Solubility
Very soluble in acetonitrile, dichloromethane or THF and less soluble in toluene.
Notes
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Incompatible with oxidizing agents.
RUO – Research Use Only
General 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).