N-Fluorobenzenesulfonimide

Base Information

• Chemical Name: N-Fluorobenzenesulfonimide
• CAS No.: 133745-75-2
• Molecular Formula: C12H10FNO4S2
• Molecular Weight: 315.346
• Hs Code.: 29242990
• European Community (EC) Number: 431-940-3,603-762-8
• UNII: 38TGL3A00I
• DSSTox Substance ID: DTXSID10343177
• Nikkaji Number: J456.242I
• Wikidata: Q27256818
• ChEMBL ID: CHEMBL1338788
• Mol file: 133745-75-2.mol

Synonyms:(18F)-N-fluorobenzenesulfonimide;N-fluorobenzenesulfonimide

Chemical Property of N-Fluorobenzenesulfonimide

Chemical Property:

• Appearance/Colour: Off-white to light brown crystalline
• Vapor Pressure: 0.0162mmHg at 25°C
• Melting Point: 114-116 °C
• Refractive Index: 1.424
• Boiling Point: 471.4 °C at 760 mmHg
• PKA: -32.45±0.70(Predicted)
• Flash Point: 238.9 °C
• PSA: 88.28000
• Density: 1.476 g/cm³
• LogP: 4.11230
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Very soluble in acetonitrile, dichloromethane or THF and less so
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 315.00352831
• Heavy Atom Count: 20
• Complexity: 461

Purity/Quality:

99% ^*data from raw suppliers

N-Fluorobenzenesulfonimide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,O
• Hazard Codes: Xi,O
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)S(=O)(=O)N(F)S(=O)(=O)C2=CC=CC=C2
• Uses: Versatile fluorinating reagent used in the fluorination of aryls, enolates, carbanions, organolithiums, etc. 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.

Technology Process of N-Fluorobenzenesulfonimide

There total 3 articles about N-Fluorobenzenesulfonimide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

→ N-fluorobis(benzenesulfon)imide (133745-75-2)

Guidance literature:

Reference yield:

→ N-fluorobis(benzenesulfon)imide (133745-75-2) + Flurithromycin (82664-20-8)

Guidance literature:

Reference yield:

dibenzenesulfonamide (2618-96-4) → N-fluorobis(benzenesulfon)imide (133745-75-2)

Guidance literature:

dibenzenesulfonamide; With sodium hydroxide; In water; for 0.333333h;

With fluorine; In acetonitrile; at -30 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2013.04.037

upstream raw materials:

dibenzenesulfonamide

Downstream raw materials:

p-Nitrobenzoyl-tert-butylnitroxid

benzoyl-tert-butylnitroxyl radical

C₁₁H₁₅FNO

methyl (2S)-fluoro[(1R,5R)-5-hydroxycyclopent-2-en-1-yl] acetate

Refernces

• 1、 -. "Preparation of (8S)-8-fluoroerythromycins with N-F fluorinating agents". . . Retrieved 2008/06/13.
• 2、 -. "N-fluorosulfonimides and their application as fluorinating agents". . . Retrieved 2008/06/13.