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N-Fluorobenzenesulfonimide

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Name

N-Fluorobenzenesulfonimide

EINECS -0
CAS No. 133745-75-2 Density 1.476 g/cm3
PSA 88.28000 LogP 4.11230
Solubility N/A Melting Point 114-116 °C
Formula C12H10FNO4S2 Boiling Point 471.4 °C at 760 mmHg
Molecular Weight 315.346 Flash Point 238.9 °C
Transport Information N/A Appearance Off-white to light brown crystalline
Safety 26-37/39 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 133745-75-2 (N-Fluorobenzenesulfonimide) Hazard Symbols IrritantXi,OxidizingO
Synonyms

N-(benzenesulfonyl)-N-fluoro-benzenesulfonamide;N-Fluorobenzenesulfoniminde;N-Fluoro Dibenzenesulfonic amide;N-Fluorodibenzenesulfonimide (NFSI);N-Fluorodi(benzenesulfonyl)amine;

Article Data 4

N-Fluorobenzenesulfonimide Synthetic route

2618-96-4

dibenzenesulfonamide

133745-75-2

N-fluorobis(benzenesulfon)imide

Conditions
ConditionsYield
Stage #1: dibenzenesulfonamide With sodium hydroxide In water for 0.333333h;
Stage #2: With fluorine In acetonitrile at -30℃; Inert atmosphere;
133745-75-2

N-fluorobis(benzenesulfon)imide

Quinine 4-chlorobenzoate

N-fluoro-p-chlorobenzoylquininium dibenzenesulfonimidate

Conditions
ConditionsYield
With Selectfluor In acetonitrile at 20℃; for 0.5h;100%

2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate

133745-75-2

N-fluorobis(benzenesulfon)imide

A

2564-83-2, 45842-10-2

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical

B

2618-96-4

dibenzenesulfonamide

Conditions
ConditionsYield
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%
133745-75-2

N-fluorobis(benzenesulfon)imide

130-95-0

Quinine

C12H10NO4S2(1-)*C20H24FN2O2(1+)

Conditions
ConditionsYield
In acetonitrile for 0.5h;100%
123-51-3

i-Amyl alcohol

133745-75-2

N-fluorobis(benzenesulfon)imide

N-(3-methylbutyl)bis(benzenesulfon)imide

Conditions
ConditionsYield
With triphenylphosphine In dichloromethane for 4h; Heating;99%
1576-96-1

(E)-2-penten-1-ol

133745-75-2

N-fluorobis(benzenesulfon)imide

C17H19NO4S2

Conditions
ConditionsYield
With triphenylphosphine In dichloromethane for 4h; Heating;99%
121-98-2

methyl 4-methoxybenzoate

133745-75-2

N-fluorobis(benzenesulfon)imide

1453100-97-4

methyl 4-methoxy-3-(N-(phenylsulfonyl)phenylsulfonamido)benzoate

Conditions
ConditionsYield
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%
874-90-8

4-methoxybenzonitrile

133745-75-2

N-fluorobis(benzenesulfon)imide

1453100-99-6

N-(5-cyano-2-methoxyphenyl)-N-(phenylsulfonyl)benzenesulfonamide

Conditions
ConditionsYield
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%
100-17-4

para-methoxynitrobenzene

133745-75-2

N-fluorobis(benzenesulfon)imide

1453101-02-4

N-(2-methoxy-5-nitrophenyl)-N-(phenylsulfonyl)benzenesulfonamide

Conditions
ConditionsYield
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%
133745-75-2

N-fluorobis(benzenesulfon)imide

121-97-1

4-Methoxypropiophenone

1453101-04-6

N-(2-methoxy-5-propionylphenyl)-N-(phenylsulfonyl)benzenesulfonamide

Conditions
ConditionsYield
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-Fluorobenzenesulfonimide Specification

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: XiIrritant,OOxidizing
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

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