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CAS No.: | 133745-75-2 |
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Name: | N-Fluorobenzenesulfonimide |
Article Data: | 4 |
Molecular Structure: | |
Formula: | C12H10FNO4S2 |
Molecular Weight: | 315.346 |
Synonyms: | N-(benzenesulfonyl)-N-fluoro-benzenesulfonamide;N-Fluorobenzenesulfoniminde;N-Fluoro Dibenzenesulfonic amide;N-Fluorodibenzenesulfonimide (NFSI);N-Fluorodi(benzenesulfonyl)amine; |
EINECS: | -0 |
Density: | 1.476 g/cm3 |
Melting Point: | 114-116 °C |
Boiling Point: | 471.4 °C at 760 mmHg |
Flash Point: | 238.9 °C |
Appearance: | Off-white to light brown crystalline |
Hazard Symbols: | Xi,O |
Risk Codes: | 36/37/38 |
Safety: | 26-37/39 |
PSA: | 88.28000 |
LogP: | 4.11230 |
dibenzenesulfonamide
N-fluorobis(benzenesulfon)imide
Conditions | Yield |
---|---|
Stage #1: dibenzenesulfonamide With sodium hydroxide In water for 0.333333h; Stage #2: With fluorine In acetonitrile at -30℃; Inert atmosphere; |
N-fluorobis(benzenesulfon)imide
Conditions | Yield |
---|---|
With Selectfluor In acetonitrile at 20℃; for 0.5h; | 100% |
N-fluorobis(benzenesulfon)imide
A
2,2,6,6-Tetramethyl-1-piperidinyloxy free radical
B
dibenzenesulfonamide
Conditions | Yield |
---|---|
With 1,1,1,2,2,2-hexamethyldisilane; copper(l) chloride In acetonitrile at 70℃; for 1h; Schlenk technique; Inert atmosphere; | A 86% B 100% |
Conditions | Yield |
---|---|
In acetonitrile for 0.5h; | 100% |
i-Amyl alcohol
N-fluorobis(benzenesulfon)imide
Conditions | Yield |
---|---|
With triphenylphosphine In dichloromethane for 4h; Heating; | 99% |
Conditions | Yield |
---|---|
With triphenylphosphine In dichloromethane for 4h; Heating; | 99% |
methyl 4-methoxybenzoate
N-fluorobis(benzenesulfon)imide
methyl 4-methoxy-3-(N-(phenylsulfonyl)phenylsulfonamido)benzoate
Conditions | Yield |
---|---|
With [Ag(2,2'-bipyridine)2](ClO4); C20H28N4O2Pd*2CHF3O3S In acetonitrile at 23℃; for 24h; Temperature; Inert atmosphere; Sealed tube; | 99% |
With [Ag(2,2'-bipyridine)2](ClO4); C20H28N4O2Pd(2+)*2CF3O3S(1-) In acetonitrile at 23℃; for 24h; Temperature; Time; Reagent/catalyst; Inert atmosphere; Sealed tube; | 99% |
4-methoxybenzonitrile
N-fluorobis(benzenesulfon)imide
N-(5-cyano-2-methoxyphenyl)-N-(phenylsulfonyl)benzenesulfonamide
Conditions | Yield |
---|---|
With [Ag(2,2'-bipyridine)2](ClO4); C20H28N4O2Pd*2CHF3O3S In acetonitrile at 23℃; for 24h; Inert atmosphere; Sealed tube; | 99% |
With [Ag(2,2'-bipyridine)2](ClO4); C20H28N4O2Pd(2+)*2CF3O3S(1-) In acetonitrile at 23℃; for 24h; Inert atmosphere; Sealed tube; | 99% |
para-methoxynitrobenzene
N-fluorobis(benzenesulfon)imide
N-(2-methoxy-5-nitrophenyl)-N-(phenylsulfonyl)benzenesulfonamide
Conditions | Yield |
---|---|
With [Ag(2,2'-bipyridine)2](ClO4); C20H28N4O2Pd*2CHF3O3S In acetonitrile at 23℃; for 24h; Inert atmosphere; Sealed tube; | 99% |
With [Ag(2,2'-bipyridine)2](ClO4); C20H28N4O2Pd(2+)*2CF3O3S(1-) In acetonitrile at 23℃; for 24h; Inert atmosphere; Sealed tube; | 99% |
N-fluorobis(benzenesulfon)imide
4-Methoxypropiophenone
N-(2-methoxy-5-propionylphenyl)-N-(phenylsulfonyl)benzenesulfonamide
Conditions | Yield |
---|---|
With [Ag(2,2'-bipyridine)2](ClO4); C20H28N4O2Pd*2CHF3O3S In acetonitrile at 23℃; for 24h; Inert atmosphere; Sealed tube; | 99% |
With [Ag(2,2'-bipyridine)2](ClO4); C20H28N4O2Pd(2+)*2CF3O3S(1-) In acetonitrile at 23℃; for 24h; Inert atmosphere; Sealed tube; | 99% |
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1. Introduction of N-Fluorobenzenesulfonimide
N-Fluorobenzenesulfonimide, is a stable crystalline solid that is easy to handle, non-hygroscopic, soluble in most common ethereal and chlorinated solvents. A neutral N–F-containing electrophilic fluorinating agent that readily transfers F+ to neutral and carbanionic nucleophiles ranging from very reactive organometallic species to slightly activated aromatic compounds. Reagent employed in a palladium-catalyzed enantioselective fluorination of β-keto esters, and α-cyano acetates, t-butoxycarbonyl lactones and lactams. Also used in the preparation of aryl (difluoromethylenephosphonates), 20-deoxy-20-fluorocamptothecin, N-fluoro sulfonamides, 2-amino-5-fluorothiazole hydrochloride and benzylic α,α-difluoronitriles, -tetrazoles, and -sulfonates. The IUPAC Name of it is N-(benzenesulfonyl)-N-fluorobenzenesulfonamide.
2. Properties of N-Fluorobenzenesulfonimide
Appearance: Off-white to light brown crystalline powder
Melting Point: 114-116 °C
Boiling point: 471.4 °C at 760 mmHg
Flash Point: 238.9 °C
Density: 1.476 g/cm3
Index of Refraction: 1.6
Molar Refractivity: 73.1 cm3
Molar Volume: 213.5 cm3
Surface Tension: 51.5 dyne/cm
Enthalpy of Vaporization: 73.42 kJ/mol
Vapour Pressure: 4.67E-09 mmHg at 25°C
XLogP3-AA: 2.6
H-Bond Donor: 0
H-Bond Acceptor: 6
3. Structure Descriptors of N-Fluorobenzenesulfonimide
Canonical SMILES: C1=CC=C(C=C1)S(=O)(=O)N(F)S(=O)(=O)C2=CC=CC=C2
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
Product Categories: Electrophilic Fluorinating Reagents; Fluorinating Reagents; Fluorinating Reagents & Building Blocks for Fluorinated Biochemical Compounds; Fluorination; Halogenation; Synthetic Organic Chemistry
4. Safety Information of N-Fluorobenzenesulfonimide
Hazard Codes: Xi,O
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 3
F: 10
Hazard Note: Oxidising Agent
HazardClass: IRRITANT