N-(benzenesulfonyl)-S-phenylfluoranesulfonamido

• ChemBase ID: 7941
• Molecular Formular: C12H10FNO4S2
• Molecular Mass: 315.3405032
• Monoisotopic Mass: 315.00352803
• SMILES: c1cccc(c1)S(=O)(=O)N(F)S(=O)(=O)c1ccccc1
• Canonical SMILES: FN(S(=O)(=O)c1ccccc1)S(=O)(=O)c1ccccc1
• InChI: InChI=1S/C12H10FNO4S2/c13-14(19(15,16)11-7-3-1-4-8-11)20(17,18)12-9-5-2-6-10-12/h1-10H
• InChIKey: RLKHFSNWQCZBDC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(benzenesulfonyl)-S-phenylfluoranesulfonamido
• IUPAC Traditional name: N-(benzenesulfonyl)-S-phenylfluoranesulfonamido
• Synonyms: AccuFluor NFSi; N-Fluorobis(phenylsulfonyl)amine; N-Fluorodi(benzenesulfonyl)amine; N-Fluorodibenzenesulfonimide; N-Fluorobenzenesulfonimide; N-Fluoro-N-(phenylsulphonyl)benzenesulphonamide; N-Fluorodibenzenesulphonimide; NFSI; N-Fluorobis(phenylsulphonyl)amine; N-Fluorobenzenesulfonimide; N-Fluorobenzenesulfonimide; N-Fluorobis(phenylsulfonyl)amine; N-Fluoro-N-(phenylsulfonyl)benzenesulfonaMide; N-氟二苯磺酰胺; N-氟代双苯磺酰胺; N-氟苯磺酰亚胺; N-氟苯磺酰亚胺; N-氟代双苯磺酰胺

Database IDs

• CAS Number: 133745-75-2
• EC Number: 000-000-0
• MDL Number: MFCD00144885
• Beilstein Number: 5348902
• PubChem SID: 24864479; 160971248
• PubChem CID: 588007

CALCULATED PROPERTIES

• LogD (pH = 5.5): 2.652075
• LogD (pH = 7.4): 2.652075
• Log P: 2.652075
• Molar Refractivity: 72.2331 cm^3
• Polarizability: 29.161053 Å^3
• Polar Surface Area: 71.52 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true
• H Acceptors: 4
• H Donor: 0

PROPERTIES

Physical Property

• Melting Point: 110 °C (dec.)(lit.); 110-118(dec.)°C; 114-116 °C; 114-116°C; 114-118°C

Safety Information

• Storage Warning: IRRITANT; Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (N); 97%; 98%
• Grade: purum
• Linear Formula: (C6H5SO2)2NF
• Empirical Formula (Hill Notation): C12H10FNO4S2

DETAILS

Apollo Scientific Ltd - PC3487

Electrophilic fluorinating agent. Ask for tech. literature .60.2mg/g active fluorine. Solubility: THF 0.24g/ml; CH2Cl2 0.4g/ml; CH3CN 0.25g/ml; Toluene 0.09g/ml.

Sigma Aldrich - 392715

Application
Reagent employed in a palladium-catalyzed enantioselective fluorination of t-butoxycarbonyl lactones and lactams.1 Also used in the electrophilic difluorination of dihalopyridines with butyl lithium2 and in the direct conversion of alcohols to dibenzenesulfonamides with triphenylphosphine.3
Stable, easy-to-handle, crystalline material which readily transfers F+ to enolates and carbanions.
Packaging
5, 500 g in poly bottle

Sigma Aldrich - 46836

Other Notes
Convenient reagent for electrophilic fluorination 1,2,3

REFERENCES

• 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).