392715

N-Fluorobenzenesulfonimide

97%

• Synonym(s): N-Fluorodi(benzenesulfonyl)amine, N-Fluorodibenzenesulfonimide, NFSI
• Linear Formula: (C₆H₅SO₂)₂NF
• CAS Number: 133745-75-2
• Molecular Weight: 315.34
• Beilstein: 5348902
• MDL number: MFCD00144885
• UNSPSC Code: 12352101
• PubChem Substance ID: 24864479
• NACRES: NA.22

Properties

• Quality Level: 100
• Assay: 97%
• form: powder
• mp: 110 °C (dec.) (lit.)
• SMILES string: FN(S(=O)(=O)c1ccccc1)S(=O)(=O)c2ccccc2
• 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
• InChI key: RLKHFSNWQCZBDC-UHFFFAOYSA-N

Description

General description

N-Fluorobenzenesulfonimide (NFSi) is a commonly used electrophilic fluorinating agent in organic synthesis to introduce fluorine into neutral organic molecules. It is also used to fluorinate nucleophilic substrates such as reactive organometallic species and malonate anions.
NFSi can be synthesized by the reaction of benzenesulfonimide with fluorine.

Application

Reagent employed in a palladium-catalyzed enantioselective fluorination of t-butoxycarbonyl lactones and lactams. Also used in the electrophilic difluorination of dihalopyridines with butyl lithium and in the direct conversion of alcohols to dibenzenesulfonamides with triphenylphosphine.

Stable, easy-to-handle, crystalline material which readily transfers F⁺ to enolates and carbanions.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H315,H319,H335
• Precautionary Statements: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves