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133745-75-2

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133745-75-2 Usage

Chemical Properties

Off-white to light brown crystalline powder

Uses

Different sources of media describe the Uses of 133745-75-2 differently. You can refer to the following data:
1. Versatile fluorinating reagent used in the fluorination of aryls, enolates, carbanions, organolithiums, etc.
2. 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.

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.

Check Digit Verification of cas no

The CAS Registry Mumber 133745-75-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,3,7,4 and 5 respectively; the second part has 2 digits, 7 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 133745-75:
(8*1)+(7*3)+(6*3)+(5*7)+(4*4)+(3*5)+(2*7)+(1*5)=132
132 % 10 = 2
So 133745-75-2 is a valid CAS Registry Number.
InChI:InChI=1/C9H4F6O2/c10-8(11,12)5-2-1-4(7(16)17)3-6(5)9(13,14)15/h1-3H,(H,16,17)

133745-75-2 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (F0335)  N-Fluorobenzenesulfonimide [Fluorinating Reagent]  >97.0%(T)

  • 133745-75-2

  • 5g

  • 344.00CNY

  • Detail
  • TCI America

  • (F0335)  N-Fluorobenzenesulfonimide [Fluorinating Reagent]  >97.0%(T)

  • 133745-75-2

  • 25g

  • 920.00CNY

  • Detail
  • Alfa Aesar

  • (L13955)  N-Fluorobenzenesulfonimide, 97%   

  • 133745-75-2

  • 1g

  • 192.0CNY

  • Detail
  • Alfa Aesar

  • (L13955)  N-Fluorobenzenesulfonimide, 97%   

  • 133745-75-2

  • 5g

  • 678.0CNY

  • Detail
  • Alfa Aesar

  • (L13955)  N-Fluorobenzenesulfonimide, 97%   

  • 133745-75-2

  • 25g

  • 2638.0CNY

  • Detail
  • Aldrich

  • (392715)  N-Fluorobenzenesulfonimide  97%

  • 133745-75-2

  • 392715-5G

  • 881.01CNY

  • Detail

133745-75-2Synthetic route

dibenzenesulfonamide
2618-96-4

dibenzenesulfonamide

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

N-fluorobis(benzenesulfon)imide

Quinine 4-chlorobenzoate

Quinine 4-chlorobenzoate

N-fluoro-p-chlorobenzoylquininium dibenzenesulfonimidate

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

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

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

N-fluorobis(benzenesulfon)imide

A

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical
2564-83-2, 45842-10-2

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

B

dibenzenesulfonamide
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%
N-fluorobis(benzenesulfon)imide
133745-75-2

N-fluorobis(benzenesulfon)imide

Quinine
130-95-0

Quinine

C12H10NO4S2(1-)*C20H24FN2O2(1+)

C12H10NO4S2(1-)*C20H24FN2O2(1+)

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

i-Amyl alcohol

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

N-fluorobis(benzenesulfon)imide

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

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

Conditions
ConditionsYield
With triphenylphosphine In dichloromethane for 4h; Heating;99%
(E)-2-penten-1-ol
1576-96-1

(E)-2-penten-1-ol

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

N-fluorobis(benzenesulfon)imide

C17H19NO4S2

C17H19NO4S2

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

methyl 4-methoxybenzoate

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

N-fluorobis(benzenesulfon)imide

methyl 4-methoxy-3-(N-(phenylsulfonyl)phenylsulfonamido)benzoate
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%
4-methoxybenzonitrile
874-90-8

4-methoxybenzonitrile

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

N-fluorobis(benzenesulfon)imide

N-(5-cyano-2-methoxyphenyl)-N-(phenylsulfonyl)benzenesulfonamide
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%
para-methoxynitrobenzene
100-17-4

para-methoxynitrobenzene

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

N-fluorobis(benzenesulfon)imide

N-(2-methoxy-5-nitrophenyl)-N-(phenylsulfonyl)benzenesulfonamide
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%
N-fluorobis(benzenesulfon)imide
133745-75-2

N-fluorobis(benzenesulfon)imide

4-Methoxypropiophenone
121-97-1

4-Methoxypropiophenone

N-(2-methoxy-5-propionylphenyl)-N-(phenylsulfonyl)benzenesulfonamide
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%
1-ethynyl-3-methoxybenzene
768-70-7

1-ethynyl-3-methoxybenzene

diphenyl diselenide
1666-13-3

diphenyl diselenide

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

N-fluorobis(benzenesulfon)imide

(E)-N-(1-(3-methoxyphenyl)-2-(phenylselanyl)vinyl)-N-(phenylsulfonyl)benzenesulfonamide

(E)-N-(1-(3-methoxyphenyl)-2-(phenylselanyl)vinyl)-N-(phenylsulfonyl)benzenesulfonamide

Conditions
ConditionsYield
In dichloromethane at 20℃; for 2h; stereoselective reaction;99%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

4-isopropyl-1-cyclopropylbenzene
27546-49-2

4-isopropyl-1-cyclopropylbenzene

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

N-fluorobis(benzenesulfon)imide

C25H26N2O4S2

C25H26N2O4S2

Conditions
ConditionsYield
With (4S)-2,2'-(1-phenylmethyl-2-phenylethylidene)bis[4-(1-methylethyl)-4,5-dihydrooxazole]; copper(I) bromide In benzene at 25℃; for 36h; Inert atmosphere; enantioselective reaction;99%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

C15H14

C15H14

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

N-fluorobis(benzenesulfon)imide

C28H24N2O4S2

C28H24N2O4S2

Conditions
ConditionsYield
With (4S)-2,2'-(1-phenylmethyl-2-phenylethylidene)bis[4-(1-methylethyl)-4,5-dihydrooxazole]; copper(I) bromide In benzene at 25℃; for 36h; Inert atmosphere; enantioselective reaction;99%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

2-cyclopropylnaphthalene
25033-18-5

2-cyclopropylnaphthalene

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

N-fluorobis(benzenesulfon)imide

C26H22N2O4S2

C26H22N2O4S2

Conditions
ConditionsYield
With (4S)-2,2'-(1-phenylmethyl-2-phenylethylidene)bis[4-(1-methylethyl)-4,5-dihydrooxazole]; copper(I) bromide In benzene at 25℃; for 36h; Inert atmosphere; enantioselective reaction;99%
oxepane
592-90-5

oxepane

Methyl phenyldiazoacetate
22979-35-7

Methyl phenyldiazoacetate

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

N-fluorobis(benzenesulfon)imide

methyl 2-fluoro-2-phenyl-2-((6-(N-(phenylsulfonyl)phenylsulfonamido)hexyl)oxy)acetate

methyl 2-fluoro-2-phenyl-2-((6-(N-(phenylsulfonyl)phenylsulfonamido)hexyl)oxy)acetate

Conditions
ConditionsYield
at 20℃; for 12h; Irradiation;99%
1,4-dioxane
123-91-1

1,4-dioxane

α-diazo-α-phenylacetic acid benzyl ester
218792-82-6

α-diazo-α-phenylacetic acid benzyl ester

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

N-fluorobis(benzenesulfon)imide

benzyl 2-fluoro-2-phenyl-2-(2-(2-(N-(phenylsulfonyl)phenylsulfonamido)ethoxy)ethoxy)acetate

benzyl 2-fluoro-2-phenyl-2-(2-(2-(N-(phenylsulfonyl)phenylsulfonamido)ethoxy)ethoxy)acetate

Conditions
ConditionsYield
at 20℃; for 12h; Irradiation;99%
ethyl 2-(4-chlorophenyl)-2-diazoacetate

ethyl 2-(4-chlorophenyl)-2-diazoacetate

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

N-fluorobis(benzenesulfon)imide

C22H19ClFNO6S2

C22H19ClFNO6S2

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 60℃; for 48h; Kinetics; Inert atmosphere;98%
3-(4'-methoxyphenyl)propenoic acid
830-09-1

3-(4'-methoxyphenyl)propenoic acid

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

N-fluorobis(benzenesulfon)imide

C21H19NO5S2

C21H19NO5S2

Conditions
ConditionsYield
With copper(l) iodide; 1,10-Phenanthroline In N,N-dimethyl-formamide at 100℃; for 12h; Inert atmosphere;98%
cyclopropylbenzene
873-49-4

cyclopropylbenzene

(2,2’-bipyridine)Zn(CF3)2

(2,2’-bipyridine)Zn(CF3)2

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

N-fluorobis(benzenesulfon)imide

N-(phenylsulfonyl)-N-(4,4,4-trifluoro-3-phenylbutyl)benzenesulfonamide

N-(phenylsulfonyl)-N-(4,4,4-trifluoro-3-phenylbutyl)benzenesulfonamide

Conditions
ConditionsYield
With zinc trifluoromethanesulfonate; copper(II) bis(trifluoromethanesulfonate); lithium dimethylacetate at 20℃; for 24h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;98%
4-ethyl-1-cyclopropylbenzene
35076-76-7

4-ethyl-1-cyclopropylbenzene

(2,2’-bipyridine)Zn(CF3)2

(2,2’-bipyridine)Zn(CF3)2

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

N-fluorobis(benzenesulfon)imide

N-(3-(4-ethylphenyl)-4,4,4-trifluorobutyl)-N-(phenylsulfonyl)benzenesulfonamide

N-(3-(4-ethylphenyl)-4,4,4-trifluorobutyl)-N-(phenylsulfonyl)benzenesulfonamide

Conditions
ConditionsYield
With zinc trifluoromethanesulfonate; copper(II) bis(trifluoromethanesulfonate); lithium dimethylacetate at 20℃; for 24h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;98%
1-(tert-butyl)-4-cyclopropylbenzene
53578-43-1

1-(tert-butyl)-4-cyclopropylbenzene

(2,2’-bipyridine)Zn(CF3)2

(2,2’-bipyridine)Zn(CF3)2

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

N-fluorobis(benzenesulfon)imide

N-(3-(4-(tert-butyl)phenyl)-4,4,4-trifluorobutyl)-N-(phenylsulfonyl)benzenesulfonamide

N-(3-(4-(tert-butyl)phenyl)-4,4,4-trifluorobutyl)-N-(phenylsulfonyl)benzenesulfonamide

Conditions
ConditionsYield
With zinc trifluoromethanesulfonate; copper(II) bis(trifluoromethanesulfonate); lithium dimethylacetate at 20℃; for 24h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;98%
(2,2’-bipyridine)Zn(CF3)2

(2,2’-bipyridine)Zn(CF3)2

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

N-fluorobis(benzenesulfon)imide

4'-Cyclopropylphenyl acetate

4'-Cyclopropylphenyl acetate

4-(1,1,1-trifluoro-4-(N-(phenylsulfonyl)phenylsulfonamido)butan-2-yl)phenyl acetate

4-(1,1,1-trifluoro-4-(N-(phenylsulfonyl)phenylsulfonamido)butan-2-yl)phenyl acetate

Conditions
ConditionsYield
With zinc trifluoromethanesulfonate; copper(II) bis(trifluoromethanesulfonate); lithium dimethylacetate at 20℃; for 24h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;98%
(2,2’-bipyridine)Zn(CF3)2

(2,2’-bipyridine)Zn(CF3)2

4-cyclopropylphenyl 1-methylcyclopropane-1-carboxylate

4-cyclopropylphenyl 1-methylcyclopropane-1-carboxylate

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

N-fluorobis(benzenesulfon)imide

4-(1,1,1-trifluoro-4-(N-(phenylsulfonyl)phenylsulfonamido)butan-2-yl)phenyl 1-methylcyclopropane-1-carboxylate

4-(1,1,1-trifluoro-4-(N-(phenylsulfonyl)phenylsulfonamido)butan-2-yl)phenyl 1-methylcyclopropane-1-carboxylate

Conditions
ConditionsYield
With zinc trifluoromethanesulfonate; copper(II) bis(trifluoromethanesulfonate); lithium dimethylacetate at 20℃; for 24h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;98%
trans-1,2-diphenylcyclopropane
1138-47-2

trans-1,2-diphenylcyclopropane

(2,2’-bipyridine)Zn(CF3)2

(2,2’-bipyridine)Zn(CF3)2

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

N-fluorobis(benzenesulfon)imide

N-(phenylsulfonyl)-N-(4,4,4-trifluoro-1,3-diphenylbutyl)benzenesulfonamide

N-(phenylsulfonyl)-N-(4,4,4-trifluoro-1,3-diphenylbutyl)benzenesulfonamide

Conditions
ConditionsYield
With zinc trifluoromethanesulfonate; copper(II) bis(trifluoromethanesulfonate); lithium dimethylacetate at 20℃; for 24h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;98%
4-vinylbenzyl chloride
1073-67-2

4-vinylbenzyl chloride

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

N-fluorobis(benzenesulfon)imide

acetonitrile
75-05-8

acetonitrile

N-(1-(4-chlorophenyl)-2-(N-(phenylsulfonyl)phenylsulfonamido)ethyl)acetamide

N-(1-(4-chlorophenyl)-2-(N-(phenylsulfonyl)phenylsulfonamido)ethyl)acetamide

Conditions
ConditionsYield
With copper(II) bis(trifluoromethanesulfonate); phenylboronic acid at 80℃; for 2h;97%
N-benzoylpyrrole
5145-65-3

N-benzoylpyrrole

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

N-fluorobis(benzenesulfon)imide

C23H18N2O5S2

C23H18N2O5S2

Conditions
ConditionsYield
With potassium carbonate In 1,2-dichloro-ethane at 80℃; for 24h; Inert atmosphere; Sealed tube; regioselective reaction;97%
styrene
292638-84-7

styrene

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

N-fluorobis(benzenesulfon)imide

N-(1-Phenylvinyl)-N-(phenylsulfonyl)benzenesulfonamide

N-(1-Phenylvinyl)-N-(phenylsulfonyl)benzenesulfonamide

Conditions
ConditionsYield
With tris(2-methylphenyl)phosphine selenide; triethylammonium benzenesulfonimide In dichloromethane at 20℃; Inert atmosphere; regioselective reaction;97%
With diphenyl diselenide; sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 4h; regioselective reaction;72%
ethyl 2-phenyldiazoacetate
22065-57-2

ethyl 2-phenyldiazoacetate

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

N-fluorobis(benzenesulfon)imide

C22H20FNO6S2

C22H20FNO6S2

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 60℃; for 48h; Kinetics; Solvent; Temperature; Concentration; Inert atmosphere;97%
N-fluorobis(benzenesulfon)imide
133745-75-2

N-fluorobis(benzenesulfon)imide

4-diazo-3-isochromanone

4-diazo-3-isochromanone

C21H16FNO6S2

C21H16FNO6S2

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 60℃; for 48h; Inert atmosphere;97%
N-fluorobis(benzenesulfon)imide
133745-75-2

N-fluorobis(benzenesulfon)imide

ethyl α-diazo-α-(4-bromophenyl)acetate
758692-47-6

ethyl α-diazo-α-(4-bromophenyl)acetate

C22H19BrFNO6S2

C22H19BrFNO6S2

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 60℃; for 48h; Kinetics; Inert atmosphere;97%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

4-cyclopropyl-1,1'-biphenyl
35076-77-8

4-cyclopropyl-1,1'-biphenyl

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

N-fluorobis(benzenesulfon)imide

C28H24N2O4S2

C28H24N2O4S2

Conditions
ConditionsYield
With (4S)-2,2'-(1-phenylmethyl-2-phenylethylidene)bis[4-(1-methylethyl)-4,5-dihydrooxazole]; copper(I) bromide In benzene at 25℃; for 36h; Inert atmosphere; enantioselective reaction;97%

133745-75-2Upstream product

133745-75-2Relevant articles and documents

Comparative studies on the enantioselective fluorination of oxindoles with structurally modified N-fluorobenzenesulfonimides

Zhang, Yan,Yang, Xian-Jin,Xie, Tian,Chen, Guan-Long,Zhu, Wen-Hua,Zhang, Xiao-Qi,Yang, Xue-Yan,Wu, Xin-Yan,He, Xiao-Peng,He, Hao-Ming

, p. 4933 - 4937 (2013/07/25)

Structurally modified N-fluorobenzenesulfonimides (NFSIs) have been used to study the enantioselective fluorination of oxindoles in the presence of a bis-cinchona alkaloid, (DHQD)2PHAL, as the catalyst. We observe that the NFSI analogues bearin

Method for preparing N-fluorosulfonimides

-

, (2008/06/13)

The present invention relates to a process of preparing N-benzenesulfonimides comprising reacting an alkali metal salt of a sulfonimide with fluorine in the presence of water or water/organic solvent mixtures. N-fluorosulfonimides are useful as fluorinati

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