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14984-73-7 Usage

General Description

Imidodisulfurylfluoride, also known as N,N'-disulfurimidoyl difluoride, is a chemical compound with the molecular formula S2(NR)2F2. It is a strong electrophilic fluorinating agent that is used in organic synthesis to introduce fluorine atoms into various chemical compounds. Imidodisulfurylfluoride is a colorless, highly reactive liquid that is sensitive to moisture and should be handled with care due to its potential for causing severe burns and eye damage. Its ability to selectively fluorinate specific functional groups makes it a valuable tool in the development of pharmaceuticals and agrochemicals. Additionally, it has applications in the production of fluorinated polymers and materials.

Check Digit Verification of cas no

The CAS Registry Mumber 14984-73-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,9,8 and 4 respectively; the second part has 2 digits, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 14984-73:
(7*1)+(6*4)+(5*9)+(4*8)+(3*4)+(2*7)+(1*3)=137
137 % 10 = 7
So 14984-73-7 is a valid CAS Registry Number.

14984-73-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name imido-bis(sulfuric acid) difluoride

1.2 Other means of identification

Product number -
Other names HFSI

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:14984-73-7 SDS

14984-73-7Synthetic route

1,1,1,3,3,3-hexamethyl-disilazane
999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

A

trimethylsilyl fluoride
420-56-4

trimethylsilyl fluoride

B

bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

Conditions
ConditionsYield
With fluorosulfonyl fluoride In acetonitrile at 20 - 90℃; for 3h; Autoclave;A n/a
B 98%
bis(chlorosulfonyl)amine
15873-42-4

bis(chlorosulfonyl)amine

bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

Conditions
ConditionsYield
With perfluorooctylsulfonyl fluoride; hydrogen fluoride at 65 - 70℃; for 15h; Time;95.3%
With hydrogen fluoride; dimethyl sulfate at 90℃; for 16h; Reagent/catalyst; Inert atmosphere;90%
With zinc(II) fluoride In acetic acid butyl ester at 25℃; for 6h; Product distribution / selectivity; Inert atmosphere;79%
1,1,1,3,3,3-hexamethyl-disilazane
999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

Conditions
ConditionsYield
With fluorosulfonyl fluoride In ethyl acetate at 100℃; for 3h; Solvent; Temperature; Autoclave;95%
bis(chlorosulfonyl)amine
15873-42-4

bis(chlorosulfonyl)amine

bismuth trifluoride

bismuth trifluoride

bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

Conditions
ConditionsYield
at 20℃; for 12h; Concentration; Inert atmosphere;90%
at 20 - 50℃;Ca. 93 g
bis(chlorosulfonyl)amine
15873-42-4

bis(chlorosulfonyl)amine

hydrogen fluoride
7664-39-3

hydrogen fluoride

bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

Conditions
ConditionsYield
With chlorosulfonic acid; isocyanate de chlorosulfonyle at 160℃; under 60006 Torr; for 0.25h; Reagent/catalyst; Temperature; Pressure; Time;89%
at 130℃; for 2h; Product distribution / selectivity; Autoclave;55%
fluorosulphonic acid
7789-21-1

fluorosulphonic acid

urea
57-13-6

urea

A

sodium fluorosulfonate
14483-63-7

sodium fluorosulfonate

B

bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

Conditions
ConditionsYield
With sodium chloride In dichloromethane distn. of a react.-mixt. of urea and HSO3F under vac.; distillate dissolved in CH2Cl2; NaCl added; stirred for 6 h under reflux;; NaSO3F filtered off; filtrate cooled to -80°C; filtn., recrystn. (CFCl3, -80°C).;A n/a
B 87.8%
bis(chlorosulfonyl)amine
15873-42-4

bis(chlorosulfonyl)amine

zinc(II) fluoride

zinc(II) fluoride

ammonia
7664-41-7

ammonia

A

{Zn(NH3)4}(2+)*2Cl(1-)={Zn(NH3)4}Cl2

{Zn(NH3)4}(2+)*2Cl(1-)={Zn(NH3)4}Cl2

B

bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

Conditions
ConditionsYield
Stage #1: bis(chlorosulfonyl)amine; zinc(II) fluoride In acetic acid butyl ester at 25℃; for 6h; Inert atmosphere;
Stage #2: ammonia In acetic acid butyl ester; water Product distribution / selectivity;
A n/a
B 81%
chlorosulfonic acid
7790-94-5

chlorosulfonic acid

aminosulfonic acid
5329-14-6

aminosulfonic acid

thionyl fluoride
7783-42-8

thionyl fluoride

bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 80℃; under 16501.7 Torr; for 17h; Solvent; Autoclave;77%
bis(chlorosulfonyl)amine
15873-42-4

bis(chlorosulfonyl)amine

antimony(III) fluoride
7783-56-4

antimony(III) fluoride

bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

Conditions
ConditionsYield
In neat (no solvent) absence of air and moisture; slight excess amine, stirring for 4 h; fractional distn. (25°C, 0.01 Torr), decantation from residual SbCl3;70%
potassium bis(fluorosulfuryl)amide

potassium bis(fluorosulfuryl)amide

fluorosulphonic acid
7789-21-1

fluorosulphonic acid

bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

Conditions
ConditionsYield
In neat (no solvent) under dry N2; KN(SO2F)2 placed in dry Schlenk vessel and HSO3F added under stream of dry nitrogen; mixture stirred with a glass stick and allowed to stay for one hour; HN(SO2F)2 distilled off under vacuum; contains small amounts of HSO3F according to (19)F-NMR;62%
fluorosulfonyl fluoride
640723-20-2, 2699-79-8, 12769-73-2

fluorosulfonyl fluoride

aminosulfonic acid
5329-14-6

aminosulfonic acid

fluorosulphonic acid
7789-21-1

fluorosulphonic acid

bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 92℃; under 27752.8 Torr; for 10h; Solvent; Autoclave;53%
thionyl chloride
7719-09-7

thionyl chloride

fluorosulphonic acid
7789-21-1

fluorosulphonic acid

urea
57-13-6

urea

A

imido-bis(sulfuric acid) fluoride chloride
237763-01-8

imido-bis(sulfuric acid) fluoride chloride

B

bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

Conditions
ConditionsYield
In thionyl chloride under dry N2; urea placed into a flask and flask immersed to a cold water bath; thionyl chloride added; HSO3F added dropwise, then the flask fitted with a reflux condenser, connected to a CaCl2 drying tube; heated at110°C for 42 h; reaction mixture fractionally distilled under vacuum; main fraction collected in the range 45-65°C/650 Pa; mixture of HN(SO2F)2, HN(SO2Cl)(SO2F), HSO3F in a ratio of 2.9:2.3:1 according to (19)F-NMR;
thionyl chloride
7719-09-7

thionyl chloride

aminosulfonic acid
5329-14-6

aminosulfonic acid

fluorosulphonic acid
7789-21-1

fluorosulphonic acid

A

imido-bis(sulfuric acid) fluoride chloride
237763-01-8

imido-bis(sulfuric acid) fluoride chloride

B

bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

Conditions
ConditionsYield
In thionyl chloride amidosulfuric acid placed into a flask and thionyl dichloride added under dry argon; HSO3F added dropwise, then the flask fitted with a reflux condenser, connected to a CaCl2 drying tube; heated at 120°C for 38 h; reaction mixture fractionally distilled under vacuum; main fraction collected in the range 47-80°C/650 Pa; mixture of HN(SO2F)2, HN(SO2Cl)(SO2F), HSO3F in a ratio of 4.8:10.5:1 according to (19)F-NMR;
fluorosulfonyl isocyanate
1495-51-8

fluorosulfonyl isocyanate

fluorosulphonic acid
7789-21-1

fluorosulphonic acid

bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

Conditions
ConditionsYield
In not given byproducts: CO2; distilled;
potassium fluoride

potassium fluoride

bis(chlorosulfonyl)amine
15873-42-4

bis(chlorosulfonyl)amine

bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

Conditions
ConditionsYield
In acetonitrile at 25℃; for 24h;
potassium bis(fluorosulfuryl)amide

potassium bis(fluorosulfuryl)amide

perchloric acid
7601-90-3

perchloric acid

bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

fluorosulfonyl fluoride
640723-20-2, 2699-79-8, 12769-73-2

fluorosulfonyl fluoride

ammonia
7664-41-7

ammonia

bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

Conditions
ConditionsYield
With N,N,N'N'-tetramethyl-1,3-propanediamine In acetonitrile at 11 - 25℃; under 123 - 760 Torr; for 13h; Product distribution / selectivity; Industry scale;
fluorosulphonic acid
7789-21-1

fluorosulphonic acid

urea
57-13-6

urea

bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

Conditions
ConditionsYield
at 120℃; Large scale;
dimethylmercury
593-74-8

dimethylmercury

bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

MeHg(N(SO2F)2)

MeHg(N(SO2F)2)

Conditions
ConditionsYield
In dichloromethane at 0 - 20℃; Schlenk technique; Inert atmosphere;100%
tetramethylstannane
594-27-4

tetramethylstannane

bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

trimethyltin(IV) di(fluorosulfonyl)amide
7240-46-2

trimethyltin(IV) di(fluorosulfonyl)amide

Conditions
ConditionsYield
In dichloromethane N2 atm.; equimolar ratio, refluxing (4 h); evapn.; elem. anal.;97%
bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

cyhexatin
13121-70-5

cyhexatin

tricyclohexyltin(IV)-di(fluorosulfonyl)amide
187884-60-2

tricyclohexyltin(IV)-di(fluorosulfonyl)amide

Conditions
ConditionsYield
With Na2SO4 In dichloromethane N2 atm.; equimolar ratio, stirring (1 h); filtn., evapn. (vac.); elem. anal.;97%
ammonia
7664-41-7

ammonia

bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

ammonium imido-bis(sulfuric acid fluoride)

ammonium imido-bis(sulfuric acid fluoride)

Conditions
ConditionsYield
In trichlorofluoromethane dropwise addn. of CFCl3 to HN(SO2F)2 (exclusion of moisture), NH3 flow is passed into this soln. at room temp. until ppt. dissolves; evapn. under reduced pressure, washing with CFCl3, elem. anal.;96.5%
bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

bis(fluorosulfonyl)imide lithium salt

bis(fluorosulfonyl)imide lithium salt

Conditions
ConditionsYield
With lithium acetate; acetic acid at 0 - 5℃; for 4h; Reagent/catalyst;94.9%
With lithium hydroxide In water Product distribution / selectivity;90%
With lithium fluoride; carbonic acid dimethyl ester at 0 - 5℃; for 3h; Reagent/catalyst;
zinc(II) trifluoroacetate
21907-47-1

zinc(II) trifluoroacetate

bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

zinc salt of bis[di(fluorosulfonyl)]amine

zinc salt of bis[di(fluorosulfonyl)]amine

Conditions
ConditionsYield
In trifluoroacetic acid byproducts: CF3COOH; Excess of HN(SO2F)2 is added to Zn(OOCCF3)2, the mixture is refluxed for 16 h.; compd. is filtered, washed with CF3COOH, CH2Cl2, dried in vacuo at 80°C, elem. anal.;92%
lithium carbonate
554-13-2

lithium carbonate

bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

bis(fluorosulfonyl)imide lithium salt

bis(fluorosulfonyl)imide lithium salt

Conditions
ConditionsYield
In water at -78 - 20℃; pH=7;92%
In water pH=7;
cobalt trifluoroacetate
6185-58-6, 24517-83-7, 50517-80-1

cobalt trifluoroacetate

bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

cobalt(II) bis(fluorosulphuryl)imide

cobalt(II) bis(fluorosulphuryl)imide

Conditions
ConditionsYield
In trifluoroacetic acid Addn. of excess HN(SO2F)2 to Co(O2CCF3) soln. under N2, refluxing (14 h), pink solid forms.; Filtn. under positive N2 pressure, washing (trifluoroacetic acid, CH2Cl2), drying in vac., elem. anal.;91%
Tetramethylblei-(IV)
75-74-1

Tetramethylblei-(IV)

bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

trimethyllead(IV)-di(fluorosulfonyl)amide
187884-58-8

trimethyllead(IV)-di(fluorosulfonyl)amide

Conditions
ConditionsYield
In dichloromethane N2 atm.; refluxing (3 h); evapn., recrystn. (CH2Cl2/petroleum ether 3/1); elem. anal.;87%
xenon difluoride
13709-36-9

xenon difluoride

bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

fluoro[imidobis(sulfuryl fluoride)]xenon(II)
53719-78-1

fluoro[imidobis(sulfuryl fluoride)]xenon(II)

Conditions
ConditionsYield
In Dichlorodifluoromethane byproducts: HF; HN(SO2F)2 syringed onto vessel with XeF2 cooled to -196°C, dry CF2Cl2 condensed onto sample at -196°C, warmed to 0°C with vigorously agitation, when formed HF extd. into upper CF2Cl2 layer, mixt. stood for 1 d at 0°C; volatiles removed in vac. at 0°C, tube and contents allowed to warm to room temp., pumped;86%
xenon fluoride

xenon fluoride

bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

fluoro[imidobis(sulfuryl fluoride)]xenon(II)
53719-78-1

fluoro[imidobis(sulfuryl fluoride)]xenon(II)

Conditions
ConditionsYield
With CF2Cl2 liquid HN(SO2F)2 was syringed onto XeF2 at -196°C, then CF2Cl2 was condenced on to the sample and warmed to 0°C with vogorous agitation for 1 day, when HF was exctrated into upper CF2Cl2 layer; CF2Cl2 and HF were removed in vac. at 0°C, a residue was warmed to room temp. and XeF2 was removed in vac.;86%
xenon difluoride
13709-36-9

xenon difluoride

bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

A

fluoro[imidobis(sulfuryl fluoride)]xenon(II)
53719-78-1

fluoro[imidobis(sulfuryl fluoride)]xenon(II)

B

hydrogen fluoride
7664-39-3

hydrogen fluoride

Conditions
ConditionsYield
In Dichlorodifluoromethane 3 d at 0°C, 1:1 molar ratio; The reactor was pumped for 3 h at 0°C to remove the byproducts, elem. anal.;A 80%
B n/a
bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

lithium hydroxide
1310-65-2

lithium hydroxide

bis(fluorosulfonyl)imide lithium salt

bis(fluorosulfonyl)imide lithium salt

Conditions
ConditionsYield
In isopropyl alcohol at 20℃; for 7h;73%
tetramethylgermane
865-52-1

tetramethylgermane

bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

trimethylgermyl-di(fluorosulfonyl)amine
187884-57-7

trimethylgermyl-di(fluorosulfonyl)amine

Conditions
ConditionsYield
In dichloromethane N2 atm.; 18 h, 20°C; evapn., distn. (vac.); elem. anal.;63%
Tetraphenyllead
595-89-1

Tetraphenyllead

bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

triphenyllead(IV)-di(fluorosulfonyl)amide
187884-62-4

triphenyllead(IV)-di(fluorosulfonyl)amide

Conditions
ConditionsYield
In dichloromethane N2 atm.; equimolar ratio, refluxing (2 d); filtn., evapn., washing (CCl4), drying (vac.); elem. anal.;43%
xenon difluoride
13709-36-9

xenon difluoride

bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

A

Xe[N(SO2F)2]2
85883-06-3

Xe[N(SO2F)2]2

B

hydrogen fluoride
7664-39-3

hydrogen fluoride

Conditions
ConditionsYield
In Dichlorodifluoromethane byproducts: [N(SO2F)2]2, SO2F2, HF; 2 weeks from -22°C to -12°C, 2:1 molar ratio; The reactor was pumped at -4°C to remove the byproducts, elem. anal.;A 20%
B n/a
cadmium(II) trifluoroacetate
37054-04-9

cadmium(II) trifluoroacetate

bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

cadmium(II) bis(bis(fluorosulphuryl)imide)

cadmium(II) bis(bis(fluorosulphuryl)imide)

Conditions
ConditionsYield
In trifluoroacetic acid byproducts: CF3COOH; Excess of HN(SO2F)2 is added to Cd(OOCCF3)2, the mixture is refluxed for 16 h.; compd. is filtered, washed with CF3COOH, CH2Cl2, dried in vacuo at 80°C, elem. anal.;>90

14984-73-7Relevant articles and documents

Synthesis of Poly- And the First Perfluoroalkyl-N(SO2F)2 Derivatives: Improved Methods for the Preparation of XN(SO2F)2 (X = H, Cl) and Single-Crystal Diffraction Studies of HN(SO2Cl)2, HN(SO2F)2, and CF3CH2N(SO2F)2

Krumm, Burkhard,Vij, Ashwani,Kirchmeier, Robert L.,JeaN'Ne,Shreeve

, p. 6295 - 6303 (1998)

The preparation of HN(SO2F)2 was achieved conveniently by fluorination of HN(SO2C1)2 with SbF3. Reactions of Hg[N(SO2F)2]2 with fluoroalkyl iodides RI (R = i-C3F7CH2CH2 and CF3CH2) gave i-C3F7CH2CH2N(SO2F) 2 (1) and CF3CH2N(SO2F)2 (2). The chlorination of Hg[N(SO2F)2]2 provided a high-yield method of synthesizing the well-known ClN(SO2F)2. N-alkylation of ClN(SO2F)2 with fluorinated ethenes CF2=CHal2 (CHal2 = CF2, CFCl, and CCl2) resulted in the formation of CF2ClCF2N(SO2F)2 (3), CF2ClCFClN(SO2F)2 (4a, major), CFCl2-CF2N(SO2F)2 (4b, minor), and CCl3CF2N(SO2F)2 (5). The synthesis of the first perfluoroalkyl-N(SO2F)2 derivatives CF3N(SO2F)2 (6), C2F5N(SO2F)2 (7), n-C3F7N(SO2F)2 (8), and n-C4F9N(SO2F)2 (9) was accomplished with moderate-to-good yields by reacting ClN(SO2F)2 with iodoperfluoroalkanes RFI (RF = CF3, C2F5, n-C3F7, and n-C4F9). Similarly, ClN(SO2F)2 reacted with CF3CH2I to give 2. Photolysis of ClN(SO2F)2 with iodoperfluoroalkanes RFI (RF = n-C3F7, and n-C4F9) gave 8 and 9 in low yields. HN(SO2F)2 belongs to a monoclinic crystal system P21 (No. 4): a = 5.1619(5) ?, b = 7.8153(8) ?, c = 6.8028(7) ?, β = 100.411(2)°, V= 269.92(5) ?3, Z= 2. HN(SO2Cl)2 is monoclinic P21/c (No. 14): a = 7.7331(3) ?, b = 10.0542(2) ?, c = 9.3197(3) ?, β = 109.495(1)°, V = 683.07(4) ?3, Z= 4. CF3CH2N(SO2F)2 is orthorhombic P212121 (No. 19): a= 11.1245(1) ?, b = 28.8003(4) ?, c = 7.7120 ?, V = 2470.90(4) ?3, Z = 12.

New inorganic ionic liquids possessing low melting temperatures and wide electrochemical windows: Ternary mixtures of alkali bis(fluorosulfonyl)amides

Kubota, Keigo,Nohira, Toshiyuki,Hagiwara, Rika

, p. 320 - 324 (2012)

Four kinds of ternary phase diagrams of alkali bis(fluorosulfonyl)amides, LiFSA-NaFSA-KFSA, LiFSA-NaFSA-CsFSA, LiFSA-KFSA-CsFSA and NaFSA-KFSA-CsFSA, have been constructed. All the ternary systems possess the only one eutectic point around equimolar compo

A bifluoride sulfonyl imide lithium salt preparation method

-

Paragraph 0046-0049, (2019/03/06)

The invention relates to an imidodisulfuryl fluoride lithium salt preparation method. The method includes steps: (1) fluoridation, to be more specific, adopting imidodisulfuryl chloride and hydrogen fluoride for synthesis of intermediate imidodisulfuryl fluoride under the action of catalysts; (2) subjecting imidodisulfuryl fluoride obtained at the step (1) to reaction with lithium carboxylate to obtain imidodisulfuryl fluoride lithium salt. The method is low in cost, low in by-product quantity and simple in aftertreatment, product quality and purity are guaranteed, and metal ion control is guaranteed especially. Therefore, the preparation method through which high-quality high-purity products can be obtained is economical and suitable for industrial production.

PROCESS FOR PREPARING BIS (FLUOROSULFONYL) IMIDE ACID AND SALTS THEREOF

-

Page/Page column 10, (2019/05/10)

A process for preparing bis(fluorosulfonyl)imide acid, comprising the reaction of sulfamic acid or a salt thereof with a halosulfuric acid and at least one fluorinating agent selected from SOF2, F-SO2-F and SF4, then the recovery of the bis(fluorosulfonyl)imide acid, is described. Also described is a process for preparing bis(fluorosulfonyl)imide salts from the bis(fluorosulfonyl)imide acid thus prepared.

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