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358-23-6

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358-23-6 Usage

Chemical Properties

clear colorless to light brown liquid

Uses

Different sources of media describe the Uses of 358-23-6 differently. You can refer to the following data:
1. Trifluoromethanesulfonic Anhydride is a strong electrophile used in chemical synthesis for introducing the triflyl group.
2. Trifluoromethanesulfonic anhydride is used to convert phenols and imine into triflic ester and NTf group. It is a strong electrophile used for the introduction of triflyl group in chemical synthesis. It serves as a reagent in the preparation of alkyl and vinyl triflates, and for the stereoselective synthesis of mannosazide methyl uronate donors. It acts as a catalyst for glycosylation with anomeric hydroxy sugars to prepare polysaccharides.

Hazard

May be corrosive to metals. Harmful if swallowed. Causes severe skin burns and eye damage.

Flammability and Explosibility

Notclassified

Synthesis

The synthesis of?Trifluoromethanesulfonic anhydride is as follows:A dry, 100-ml., round-bottomed flask is charged with 36.3 g. (0.242 mole) of trifluoromethanesulfonic acid (Note 1) and 27.3 g. (0.192 mole) of phosphorus pentoxide (Note 2). The flask is stoppered and allowed to stand at room temperature for at least 3 hours. During this period the reaction mixture changes from a slurry to a solid mass. The flask is fitted with a short-path distilling head and heated first with a stream of hot air from a heat gun and then with the flame from a small burner.The flask is heated until no more trifluoromethanesulfonic anhydride distills, b.p. 82–115°, yielding 28.4–31.2 g. (83–91%) of the anhydride, a colorless liquid. Although this product is sufficiently pure for use in the next step, the remaining acid may be removed from the anhydride by the following procedure. A slurry of 3.2 g. of phosphorus pentoxide in 31.2 g. of the crude anhydride is stirred at room temperature in a stoppered flask for 18 hours. After the reaction flask has been fitted with a short-path distilling head, it is heated with an oil bath, yielding 0.7 g. of forerun, b.p. 74–81°, followed by 27.9 g. of the pure trifluoromethanesulfonic acid anhydride, b.p. 81–84° .

storage

Store in a cool, dry, wellventilated area. ?Moisture sensitive.

Purification Methods

It can be freshly prepared from the anhydrous acid (11.5g) and P2O5 (11.5g, or half this weight) by setting aside at room temperature for 1hour, distilling off volatile products then distil it through a short Vigreux column. It is readily hydrolysed by H2O and decomposes appreciably after a few days to liberate SO2 and produce a viscous liquid. Store it dry at low temperatures. [Burdon et al. J Chem Soc 2574 1957, Beard et al. J Org Chem 38 373 1973, Beilstein 3 IV 35.]

Check Digit Verification of cas no

The CAS Registry Mumber 358-23-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,5 and 8 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 358-23:
(5*3)+(4*5)+(3*8)+(2*2)+(1*3)=66
66 % 10 = 6
So 358-23-6 is a valid CAS Registry Number.
InChI:InChI=1/C2F6O5S2/c3-1(4,5)14(9,10)13-15(11,12)2(6,7)8

358-23-6 Well-known Company Product Price

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

  • (T1100)  Trifluoromethanesulfonic Anhydride  >98.0%(T)

  • 358-23-6

  • 10g

  • 350.00CNY

  • Detail
  • TCI America

  • (T1100)  Trifluoromethanesulfonic Anhydride  >98.0%(T)

  • 358-23-6

  • 25g

  • 670.00CNY

  • Detail
  • TCI America

  • (T1100)  Trifluoromethanesulfonic Anhydride  >98.0%(T)

  • 358-23-6

  • 250g

  • 2,990.00CNY

  • Detail
  • Alfa Aesar

  • (A11767)  Trifluoromethanesulfonic anhydride, 98%   

  • 358-23-6

  • 10g

  • 552.0CNY

  • Detail
  • Alfa Aesar

  • (A11767)  Trifluoromethanesulfonic anhydride, 98%   

  • 358-23-6

  • 25g

  • 1176.0CNY

  • Detail
  • Alfa Aesar

  • (A11767)  Trifluoromethanesulfonic anhydride, 98%   

  • 358-23-6

  • 50g

  • 1989.0CNY

  • Detail
  • Alfa Aesar

  • (A11767)  Trifluoromethanesulfonic anhydride, 98%   

  • 358-23-6

  • 100g

  • 3814.0CNY

  • Detail
  • Alfa Aesar

  • (A11767)  Trifluoromethanesulfonic anhydride, 98%   

  • 358-23-6

  • 250g

  • 5179.0CNY

  • Detail
  • Sigma-Aldrich

  • (91737)  Trifluoromethanesulfonicanhydride  purum, ≥98.0% (T)

  • 358-23-6

  • 91737-5ML

  • 835.38CNY

  • Detail
  • Sigma-Aldrich

  • (91737)  Trifluoromethanesulfonicanhydride  purum, ≥98.0% (T)

  • 358-23-6

  • 91737-25ML

  • 3,161.34CNY

  • Detail
  • Sigma-Aldrich

  • (91737)  Trifluoromethanesulfonicanhydride  purum, ≥98.0% (T)

  • 358-23-6

  • 91737-100ML

  • 10,307.70CNY

  • Detail
  • Aldrich

  • (176176)  Trifluoromethanesulfonicanhydride  ≥99%

  • 358-23-6

  • 176176-5G

  • 487.89CNY

  • Detail

358-23-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name triflic anhydride

1.2 Other means of identification

Product number -
Other names TRIFLUOROMETHANESULFONIC ANHYDRIDE (10 ML )

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:358-23-6 SDS

358-23-6Synthetic route

trifluorormethanesulfonic acid
1493-13-6

trifluorormethanesulfonic acid

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

Conditions
ConditionsYield
With phosphorus pentoxide at 40 - 90℃; Concentration; Temperature; Industrial scale;96.1%
With phosphorus pentoxide at 90℃; Temperature; Large scale;96.1%
With α,α,α-trichloro-o-toluic chloride at 115 - 140℃; for 3.08h; Product distribution / selectivity;91.4%
chloroform
67-66-3

chloroform

Chlorine(I) trifluoromethanesulfonate
65597-24-2

Chlorine(I) trifluoromethanesulfonate

A

trifluorormethanesulfonic acid
1493-13-6

trifluorormethanesulfonic acid

B

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

Conditions
ConditionsYield
at 22℃; for 1h;A n/a
B 92%
methyl 3,5-di-O-benzoyl-2,6-dideoxy-2-iodo-β-D-altrofuranoside
81715-08-4, 81715-17-5

methyl 3,5-di-O-benzoyl-2,6-dideoxy-2-iodo-β-D-altrofuranoside

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

Conditions
ConditionsYield
With azobisisobutyronitrile; tri-n-butyl-tin hydride In toluene for 4h; Heating;90%
silver trifluoromethanesulfonate
2923-28-6

silver trifluoromethanesulfonate

A

iodotrifluoromethane
2314-97-8

iodotrifluoromethane

B

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

Conditions
ConditionsYield
at higher temp.;A 0.5%
B n/a
trichlorofluoromethane
75-69-4

trichlorofluoromethane

Chlorine(I) trifluoromethanesulfonate
65597-24-2

Chlorine(I) trifluoromethanesulfonate

A

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

B

Trifluoro-methanesulfonic acid dichloro-fluoro-methyl ester
74501-97-6

Trifluoro-methanesulfonic acid dichloro-fluoro-methyl ester

Conditions
ConditionsYield
at -78 - 22℃; for 15h;A 0.2%
B 4.4 mmol
Dichlorodifluoromethane
75-71-8

Dichlorodifluoromethane

Chlorine(I) trifluoromethanesulfonate
65597-24-2

Chlorine(I) trifluoromethanesulfonate

A

Carbonyl fluoride
353-50-4

Carbonyl fluoride

B

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

C

perfluorochloromethyl trifluoromethanesulfonate
74501-96-5

perfluorochloromethyl trifluoromethanesulfonate

D

difluoromethyl bis(trifluoromethanesulfonate)
74512-41-7

difluoromethyl bis(trifluoromethanesulfonate)

Conditions
ConditionsYield
at -60 - 22℃; for 15h; Further byproducts given;A 0.8 mmol
B 0.8 mmol
C 1.0 mmol
D 0.1 mmol
Dichlorodifluoromethane
75-71-8

Dichlorodifluoromethane

Bromine(I) trifluoromethanesulfonate
70142-16-4

Bromine(I) trifluoromethanesulfonate

A

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

B

trifluoromethyl trifluoromethanesulfonate
3582-05-6

trifluoromethyl trifluoromethanesulfonate

C

perfluorochloromethyl trifluoromethanesulfonate
74501-96-5

perfluorochloromethyl trifluoromethanesulfonate

D

difluoromethyl bis(trifluoromethanesulfonate)
74512-41-7

difluoromethyl bis(trifluoromethanesulfonate)

Conditions
ConditionsYield
at -111 - -50℃; for 15h; Further byproducts given;A 0.6 mmol
B 0.7 mmol
C 0.6 mmol
D 0.12 mmol
trichlorofluoromethane
75-69-4

trichlorofluoromethane

Chlorine(I) trifluoromethanesulfonate
65597-24-2

Chlorine(I) trifluoromethanesulfonate

A

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

B

fluoroformyl trifluoromethanesulfonate
74501-99-8

fluoroformyl trifluoromethanesulfonate

Conditions
ConditionsYield
at -78 - 22℃; for 24h;
dibromodifluoromethane
75-61-6

dibromodifluoromethane

Chlorine(I) trifluoromethanesulfonate
65597-24-2

Chlorine(I) trifluoromethanesulfonate

A

Carbonyl fluoride
353-50-4

Carbonyl fluoride

B

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

C

perfluorobromomethyl trifluoromethanesulfonate
74501-92-1

perfluorobromomethyl trifluoromethanesulfonate

Conditions
ConditionsYield
In Dichlorodifluoromethane at -160℃; for 1h;A 1.2 mmol
B 0.6 mmol
C 2.0 mmol
dibromodifluoromethane
75-61-6

dibromodifluoromethane

Bromine(I) trifluoromethanesulfonate
70142-16-4

Bromine(I) trifluoromethanesulfonate

A

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

B

trifluoromethyl trifluoromethanesulfonate
3582-05-6

trifluoromethyl trifluoromethanesulfonate

C

perfluorobromomethyl trifluoromethanesulfonate
74501-92-1

perfluorobromomethyl trifluoromethanesulfonate

D

difluoromethyl bis(trifluoromethanesulfonate)
74512-41-7

difluoromethyl bis(trifluoromethanesulfonate)

Conditions
ConditionsYield
at -111 - -60℃; for 24h; Further byproducts given;A 0.35 mmol
B 0.4 mmol
C 0.7 mmol
D 0.7 mmol
tribromofluoromethane
353-54-8

tribromofluoromethane

Chlorine(I) trifluoromethanesulfonate
65597-24-2

Chlorine(I) trifluoromethanesulfonate

A

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

B

fluoroformyl trifluoromethanesulfonate
74501-99-8

fluoroformyl trifluoromethanesulfonate

Conditions
ConditionsYield
In Dichlorodifluoromethane at -111℃; for 15h;A 1.8 mmol
B 1.6 mmol
trifluorormethanesulfonic acid
1493-13-6

trifluorormethanesulfonic acid

pentafluoroethyl pentafluoroethanepyrosulfonate de perfluoroethyle

pentafluoroethyl pentafluoroethanepyrosulfonate de perfluoroethyle

A

trifluoroacetyl fluoride
354-34-7

trifluoroacetyl fluoride

B

perfluoroethanesulfonic acid
354-88-1

perfluoroethanesulfonic acid

C

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

D

trifluoromethyl trifluoromethanesulfonate
3582-05-6

trifluoromethyl trifluoromethanesulfonate

Conditions
ConditionsYield
at 45℃; for 14h; Product distribution;
tris(trifluoromethanesulfonyloxy)boron
64371-01-3

tris(trifluoromethanesulfonyloxy)boron

A

Carbonyl fluoride
353-50-4

Carbonyl fluoride

B

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

C

trifluoromethyl trifluoromethanesulfonate
3582-05-6

trifluoromethyl trifluoromethanesulfonate

Conditions
ConditionsYield
In neat (no solvent) at 200℃; for 1h;
Chlorine(I) trifluoromethanesulfonate
65597-24-2

Chlorine(I) trifluoromethanesulfonate

perfluorobromomethyl trifluoromethanesulfonate
74501-92-1

perfluorobromomethyl trifluoromethanesulfonate

A

Carbonyl fluoride
353-50-4

Carbonyl fluoride

B

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

C

difluoromethyl bis(trifluoromethanesulfonate)
74512-41-7

difluoromethyl bis(trifluoromethanesulfonate)

Conditions
ConditionsYield
In Dichlorodifluoromethane at -111 - 22℃; for 24h;A 0.8 mmol
B 0.8 mmol
C 0.6 mmol
Chlorine(I) trifluoromethanesulfonate
65597-24-2

Chlorine(I) trifluoromethanesulfonate

A

chlorotrifluoromethane
75-72-9

chlorotrifluoromethane

B

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

C

CF5O4PS

CF5O4PS

Conditions
ConditionsYield
With difluorophosphinic bromide at -111 - -20℃;
Chlorine(I) trifluoromethanesulfonate
65597-24-2

Chlorine(I) trifluoromethanesulfonate

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

Conditions
ConditionsYield
With trifluorophosphane at -130 - 0℃;
(S)-Formyloxy-phenyl-acetic acid methyl ester
144125-08-6

(S)-Formyloxy-phenyl-acetic acid methyl ester

A

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

B

(S)-Methyl mandelate
21210-43-5

(S)-Methyl mandelate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol for 1h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
(R)-Phenyl-trifluoromethanesulfonyloxy-acetic acid methyl ester
120049-36-7

(R)-Phenyl-trifluoromethanesulfonyloxy-acetic acid methyl ester

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

A

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

B

(S)-Methyl mandelate
21210-43-5

(S)-Methyl mandelate

Conditions
ConditionsYield
With toluene-4-sulfonic acid 2.) MeOH, 1 h, room temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
Bis(trifluoromethyl)disulfid
372-64-5

Bis(trifluoromethyl)disulfid

A

Trifluoro-methanethiosulfonic acid S-trifluoromethyl ester
358-15-6

Trifluoro-methanethiosulfonic acid S-trifluoromethyl ester

B

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

C

Bis(trifluormethyl)disulfanoxid
63548-94-7

Bis(trifluormethyl)disulfanoxid

Conditions
ConditionsYield
With fluoro alcohol In [D3]acetonitrile; acetonitrile at -50℃; for 1h; Product distribution; other temperatures, other exposition, other products;
trifluoromethanesulphonic-p-toluenesulphonic acid anhydride
51567-94-3

trifluoromethanesulphonic-p-toluenesulphonic acid anhydride

A

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

B

p-toluenesulfonylanhydride
4124-41-8

p-toluenesulfonylanhydride

Conditions
ConditionsYield
With decalin In nitromethane at 0℃; for 3h;A 0.54 g
B 0.95 g
trifluorormethanesulfonic acid
1493-13-6

trifluorormethanesulfonic acid

bis(trifluoromethyl)diethylaminophosphane
55865-38-8

bis(trifluoromethyl)diethylaminophosphane

A

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

B

bis(trifluoromethyl)phosphinous acid
359-65-9

bis(trifluoromethyl)phosphinous acid

C

Tetrakis(trifluormethyl)disphosphoxan
2728-67-8

Tetrakis(trifluormethyl)disphosphoxan

(5-bromo-2-chlorophenyl)(4-ethylphenyl)methanone
879545-43-4

(5-bromo-2-chlorophenyl)(4-ethylphenyl)methanone

(5-bromo-2-chlorophenyl)(2-ethylphenyl)methanone
879545-44-5

(5-bromo-2-chlorophenyl)(2-ethylphenyl)methanone

A

4-bromo-1-chloro-2-(4-ethylbenzyl)benzene
879545-41-2

4-bromo-1-chloro-2-(4-ethylbenzyl)benzene

B

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

Conditions
ConditionsYield
With triethylsilane; trifluorormethanesulfonic acid In trifluoroacetic acid at 30 - 70℃; Heating / reflux;
trifluorormethanesulfonic acid
1493-13-6

trifluorormethanesulfonic acid

A

Carbonyl fluoride
353-50-4

Carbonyl fluoride

B

Hexafluoroethane
76-16-4

Hexafluoroethane

C

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

D

trifluoromethyl trifluoromethanesulfonate
3582-05-6

trifluoromethyl trifluoromethanesulfonate

Conditions
ConditionsYield
byproducts: SO3, SOF2; at 10°C;
silver trifluoromethanesulfonate
2923-28-6

silver trifluoromethanesulfonate

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

Conditions
ConditionsYield
With iodine heating above 300°C;
trichloroiodomethane
594-22-9

trichloroiodomethane

mercuric triflate
49539-99-3, 49540-00-3

mercuric triflate

A

phosgene
75-44-5

phosgene

B

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

trifluorormethanesulfonic acid
1493-13-6

trifluorormethanesulfonic acid

phosphorus pentachloride
10026-13-8, 874483-75-7

phosphorus pentachloride

A

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

B

Chlorine(I) trifluoromethanesulfonate
65597-24-2

Chlorine(I) trifluoromethanesulfonate

carbon tetrabromide
558-13-4

carbon tetrabromide

mercuric triflate
49539-99-3, 49540-00-3

mercuric triflate

A

carbonyl dibromide
593-95-3

carbonyl dibromide

B

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

trifluorormethanesulfonic acid
1493-13-6

trifluorormethanesulfonic acid

A

metaphosphoric acid

metaphosphoric acid

B

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

Conditions
ConditionsYield
With phosphorus pentoxide
ammonia
7664-41-7

ammonia

A

ammonium triflate
38542-94-8

ammonium triflate

B

Trifluoromethanesulfonamide
421-85-2

Trifluoromethanesulfonamide

C

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

Conditions
ConditionsYield
In ammonia
In ammonia aq. ammonia=NH3;
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

methyl 2-oxocyclopentane-1-carboxylate
10472-24-9

methyl 2-oxocyclopentane-1-carboxylate

methyl 2-(trifluoromethylsulfonyloxy)cyclopent-1-enecarboxylate
65832-21-5

methyl 2-(trifluoromethylsulfonyloxy)cyclopent-1-enecarboxylate

Conditions
ConditionsYield
Stage #1: methyl 2-oxocyclopentane-1-carboxylate With N-ethyl-N,N-diisopropylamine In dichloromethane at -78℃; for 0.166667h; Inert atmosphere;
Stage #2: trifluoromethylsulfonic anhydride In dichloromethane at -78 - 20℃; Inert atmosphere;
100%
With sodium hydride In diethyl ether; pentane at 20℃; for 1h;99%
With sodium hydride In diethyl ether99%
2,3;4,5-di-O-isopropylidene-β-D-fructopyranose
20880-92-6

2,3;4,5-di-O-isopropylidene-β-D-fructopyranose

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

2,3:4,5-di-O-isopropylidene-1-O-(trifluoromethanesulfonyl)-β-D-fructopyranose
74925-15-8

2,3:4,5-di-O-isopropylidene-1-O-(trifluoromethanesulfonyl)-β-D-fructopyranose

Conditions
ConditionsYield
With 2,6-di-tert-butyl-4-methylpyridine In dichloromethane at -10℃; for 0.666667h;100%
With pyridine In dichloromethane at -15℃; for 1.5h;95%
With pyridine In dichloromethane at -20℃; for 2h;92%
8-quinolinol
148-24-3

8-quinolinol

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

quinolin-8-yl trifluoromethanesulfonate
108530-08-1

quinolin-8-yl trifluoromethanesulfonate

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃; for 12h; Schlenk technique; Inert atmosphere;100%
With pyridine In dichloromethane at 0 - 20℃;99%
With pyridine In dichloromethane at 0 - 20℃;97%
benzyl 2,3-O-isopropylidene-D-ribofuranoside
23276-32-6

benzyl 2,3-O-isopropylidene-D-ribofuranoside

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

benzyl 2,3-O-isopropylidene-5-O-triflyl-β-D-ribofuranoside
70209-12-0

benzyl 2,3-O-isopropylidene-5-O-triflyl-β-D-ribofuranoside

Conditions
ConditionsYield
With pyridine In dichloromethane at -5℃; for 0.5h;100%
With pyridine In dichloromethane at -20℃; for 0.5h; Inert atmosphere;
1,2 5,6-O-di(isopropylidene)-α-D-allofuranose
620630-82-2

1,2 5,6-O-di(isopropylidene)-α-D-allofuranose

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

(3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol trifluoromethanesulfonate

(3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol trifluoromethanesulfonate

Conditions
ConditionsYield
Stage #1: 1,2 5,6-O-di(isopropylidene)-α-D-allofuranose; trifluoromethylsulfonic anhydride With pyridine In dichloromethane at -5℃; for 1h;
Stage #2: With water In dichloromethane at 20℃;
100%
With pyridine In dichloromethane at 20℃;80%
With pyridine In dichloromethane for 0.166667h;
With pyridine In dichloromethane at 0℃;
In dichloromethane at 0℃; for 5h; Inert atmosphere;
2-hydroxy-7,8,9,10-tetrahydrophenanthridine
100713-03-9

2-hydroxy-7,8,9,10-tetrahydrophenanthridine

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

2-<<(trifluoromethyl)sulfonyl>oxy>-7,8,9,10-tetrahydrophenanthridine
144127-49-1

2-<<(trifluoromethyl)sulfonyl>oxy>-7,8,9,10-tetrahydrophenanthridine

Conditions
ConditionsYield
With pyridine at 0℃; for 24h;100%
2,2'-dihydroxybiphenyl
1806-29-7

2,2'-dihydroxybiphenyl

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

2,2'-bis-<<(trifluoromethyl)sulfonyl>oxy>biphenyl
17763-95-0

2,2'-bis-<<(trifluoromethyl)sulfonyl>oxy>biphenyl

Conditions
ConditionsYield
With pyridine In dichloromethane at 0℃; Inert atmosphere;100%
With triethylamine In dichloromethane at 0 - 23℃; for 14h;99%
With pyridine97%
(S)-Methyl lactate
27871-49-4

(S)-Methyl lactate

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

methyl (S)-2-[(trifluoromethanesulfonyl)oxy]propionate
99208-98-7

methyl (S)-2-[(trifluoromethanesulfonyl)oxy]propionate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 15℃; for 2h; Inert atmosphere;100%
With 2,6-dimethylpyridine In dichloromethane at -78℃;91%
In pyridine; dichloromethane at -22 - 20℃;74.4%
(S)-Ethyl lactate
687-47-8

(S)-Ethyl lactate

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

ethyl (S)-lactate triflate
84028-88-6

ethyl (S)-lactate triflate

Conditions
ConditionsYield
With 2,6-dimethylpyridine In dichloromethane at -78 - 20℃; for 1.66667h;100%
With 2,6-dimethylpyridine In dichloromethane at 0 - 20℃;98%
With N,N-diisobutyl-2,4-dimethyl-3-pentylamine In tetrachloromethane for 0.5h; 0 deg C to RT;96%
1-Decanol
112-30-1

1-Decanol

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

1-(tert-butyldimethylsilyl)oxydecane
53059-89-5

1-(tert-butyldimethylsilyl)oxydecane

Conditions
ConditionsYield
With 2,6-dimethylpyridine In dichloromethane at 0℃; for 0.25h; Inert atmosphere;100%
With triethylamine In toluene for 0.25h; Ambient temperature;77%
With pyridine In dichloromethane at -5 - 5℃; for 3h;62%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

4-Iodophenol
540-38-5

4-Iodophenol

4-iodophenyl trifluoromethanesulfonate
109586-39-2

4-iodophenyl trifluoromethanesulfonate

Conditions
ConditionsYield
With pyridine at 0 - 20℃; for 12h; Inert atmosphere;100%
With pyridine In dichloromethane at 0℃;95%
Stage #1: p-Iodophenol With 2,6-dimethylpyridine In dichloromethane at -30℃; for 0.25h;
Stage #2: trifluoromethylsulfonic anhydride In dichloromethane at 20℃; for 4.5h;
90%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

Estrone
53-16-7

Estrone

estrone triflate
92817-04-4

estrone triflate

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere;100%
With pyridine In dichloromethane at 0 - 20℃; for 1.5h; Inert atmosphere;100%
With triethylamine In dichloromethane at 0℃; for 1h;99%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

6-Hydroxy-1-tetralone
3470-50-6

6-Hydroxy-1-tetralone

5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate
144464-64-2

5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
With pyridine at 20℃;100%
With pyridine In dichloromethane99%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

(S)-(-)-2-trifluoromethanesulfonyloxy-1,1'-binaphthyl
187522-58-3, 126613-04-5, 405877-72-7

(S)-(-)-2-trifluoromethanesulfonyloxy-1,1'-binaphthyl

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 2h;100%
With pyridine In dichloromethane for 2h;92%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester
4326-36-7

(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

methyl N-(tert-butoxycarbonyl)-O-[(trifluoromethyl)sulfonyl]-L-tyrosinate
112766-18-4

methyl N-(tert-butoxycarbonyl)-O-[(trifluoromethyl)sulfonyl]-L-tyrosinate

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 5℃; for 2.5h;100%
With 2,6-dimethylpyridine In dichloromethane at 0℃;99%
With 4-methyl-morpholine In dichloromethane at -15 - -5℃; for 2.16667h;98%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

ethyl (R)-2-hydroxy-4-phenylbutyrate
90315-82-5

ethyl (R)-2-hydroxy-4-phenylbutyrate

ethyl (R)-4-phenyl-2-<<(trifluoromethyl)sulfonyl>oxy>butyrate
88767-98-0

ethyl (R)-4-phenyl-2-<<(trifluoromethyl)sulfonyl>oxy>butyrate

Conditions
ConditionsYield
With pyridine In dichloromethane at 0℃; for 0.5h;100%
In pyridine; dichloromethane at 10℃; for 2h;85%
With pyridine In dichloromethane at 4℃; for 3h;57%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

(S)-[1,1']-binaphthalenyl-2,2'-diol
18531-99-2

(S)-[1,1']-binaphthalenyl-2,2'-diol

(S)-2,2'-bis((trifluoromethanesulfonyl)oxy)-1,1'-binaphthyl
126613-06-7, 128544-05-8, 128575-34-8, 141807-44-5

(S)-2,2'-bis((trifluoromethanesulfonyl)oxy)-1,1'-binaphthyl

Conditions
ConditionsYield
With triethylamine In dichloromethane at -78 - 20℃; for 2h; Inert atmosphere;100%
With 2,6-dimethylpyridine; dmap In dichloromethane at -78 - 20℃;100%
With pyridine In dichloromethane at 0 - 20℃; for 5h; Schlenk technique;100%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

2,2':6',2''-Terpyridin-4'(1'H)-one
128143-88-4

2,2':6',2''-Terpyridin-4'(1'H)-one

4'-{[(Trifluoromethyl)sulfonyl]oxy}-2,2':6',2''-terpyridine
134653-69-3

4'-{[(Trifluoromethyl)sulfonyl]oxy}-2,2':6',2''-terpyridine

Conditions
ConditionsYield
With pyridine at 0 - 20℃; Inert atmosphere;100%
In pyridine Inert atmosphere;94%
With pyridine 1) 0 deg C, 30 min, 2) 25 deg C, 48h;70%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

methyl (2S)-2-hydroxy-4-methylpentanoate
17392-84-6

methyl (2S)-2-hydroxy-4-methylpentanoate

(S)-methyl 4-methyl-2-{[(trifluoromethyl)sulfonyl]oxy}pentanoate
120049-34-5

(S)-methyl 4-methyl-2-{[(trifluoromethyl)sulfonyl]oxy}pentanoate

Conditions
ConditionsYield
Stage #1: trifluoromethylsulfonic anhydride; methyl (2S)-2-hydroxy-4-methylpentanoate In dichloromethane at -30℃; for 0.166667h;
Stage #2: With 2,6-dimethylpyridine In dichloromethane at 20℃; for 16h;
100%
With 2,6-dimethylpyridine In dichloromethane at -78℃;91%
With lutidine In dichloromethane at 0℃;
With 2,6-dimethylpyridine In dichloromethane at 0℃; for 0.25h; Inert atmosphere;
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

3-Deoxy-3-C-methyl-D-ribonolactone
132454-70-7

3-Deoxy-3-C-methyl-D-ribonolactone

Trifluoro-methanesulfonic acid (3R,4R,5S)-5-benzyloxymethyl-4-methyl-2-oxo-tetrahydro-furan-3-yl ester
132454-69-4

Trifluoro-methanesulfonic acid (3R,4R,5S)-5-benzyloxymethyl-4-methyl-2-oxo-tetrahydro-furan-3-yl ester

Conditions
ConditionsYield
100%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

methyl 2,3-di-O-benzoyl-6-deoxy-β-D-galactopyranoside
134645-97-9

methyl 2,3-di-O-benzoyl-6-deoxy-β-D-galactopyranoside

methyl 2,3-di-O-benzoyl-6-deoxy-4-O-trifluoromethanesulfonyl-β-D-galactopyranoside
134659-74-8

methyl 2,3-di-O-benzoyl-6-deoxy-4-O-trifluoromethanesulfonyl-β-D-galactopyranoside

Conditions
ConditionsYield
With pyridine100%
With pyridine In dichloromethane at 0℃; for 0.333333h;87%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

3α,18-pivalyldioxy-17-noraphidicolan-16-one
73697-07-1, 106758-95-6

3α,18-pivalyldioxy-17-noraphidicolan-16-one

3α,18-(2,2-dimethylpropylidenedioxy)-16-(trifluoromethylsulphonyloxy)-17-noraphidicol-15-ene
135405-00-4

3α,18-(2,2-dimethylpropylidenedioxy)-16-(trifluoromethylsulphonyloxy)-17-noraphidicol-15-ene

Conditions
ConditionsYield
With 2,6-di-tert-butyl-4-methylpyridine In dichloromethane Ambient temperature;100%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

methyl 4-O-benzoyl-2,6-dideoxy-β-D-arabino-hexopyranoside
71695-52-8

methyl 4-O-benzoyl-2,6-dideoxy-β-D-arabino-hexopyranoside

Benzoic acid (2R,3R,4R,6R)-6-methoxy-2-methyl-4-trifluoromethanesulfonyloxy-tetrahydro-pyran-3-yl ester
102650-55-5

Benzoic acid (2R,3R,4R,6R)-6-methoxy-2-methyl-4-trifluoromethanesulfonyloxy-tetrahydro-pyran-3-yl ester

Conditions
ConditionsYield
With 2,6-di-tert-butyl-4-methylpyridine In dichloromethane at 23℃; for 0.166667h;100%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

5-(4-chlorophenyl)-1,1,1-trifluoropentan-2-ol
112298-15-4

5-(4-chlorophenyl)-1,1,1-trifluoropentan-2-ol

5-(p-chlorophenyl)-1,1,1-trifluoropentan-2-ol triflate
112298-11-0

5-(p-chlorophenyl)-1,1,1-trifluoropentan-2-ol triflate

Conditions
ConditionsYield
With pyridine In dichloromethane at 0℃; for 4h;100%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

(4aS,5R)-5-Methyl-2-propyl-4a,5,6,7,8,8a-hexahydro-1H-quinolin-4-one
145411-92-3, 145411-94-5

(4aS,5R)-5-Methyl-2-propyl-4a,5,6,7,8,8a-hexahydro-1H-quinolin-4-one

Trifluoro-methanesulfonic acid (4aR,5S,8aS)-5-methyl-2-propyl-4a,5,6,7,8,8a-hexahydro-quinolin-4-yl ester; compound with trifluoro-methanesulfonic acid
145585-44-0

Trifluoro-methanesulfonic acid (4aR,5S,8aS)-5-methyl-2-propyl-4a,5,6,7,8,8a-hexahydro-quinolin-4-yl ester; compound with trifluoro-methanesulfonic acid

Conditions
ConditionsYield
In dichloromethane at 40℃; for 18h;100%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

methyl 3-O-benzoyl-2,6-dideoxy-α-D-arabino-hexopyranoside
110418-88-7

methyl 3-O-benzoyl-2,6-dideoxy-α-D-arabino-hexopyranoside

methyl 3-O-benzoyl-2,6-dideoxy-4-O-<(trifluoromethyl)sulfonyl>-α-D-arabino-hexopyranoside
110418-89-8

methyl 3-O-benzoyl-2,6-dideoxy-4-O-<(trifluoromethyl)sulfonyl>-α-D-arabino-hexopyranoside

Conditions
ConditionsYield
With 2,6-di-tert-butyl-4-methylpyridine In chloroform-d1 at 20℃; for 0.25h;100%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

(4S,5R)-2,2-dimethyl-4-(hydroxymethyl)-5-(2'-methylpropyl)-1,3-dioxolane
143444-50-2

(4S,5R)-2,2-dimethyl-4-(hydroxymethyl)-5-(2'-methylpropyl)-1,3-dioxolane

(4S,5R)-2,2-dimethyl-4-(trifluoromethanesulfonyloxymethyl)-5-(2'-methylpropyl)-1,3-dioxolane
143427-04-7

(4S,5R)-2,2-dimethyl-4-(trifluoromethanesulfonyloxymethyl)-5-(2'-methylpropyl)-1,3-dioxolane

Conditions
ConditionsYield
With pyridine In dichloromethane at -15℃; for 0.333333h;100%
With pyridine at -15℃; for 0.25h;
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

3-amino>-1-propanol
112403-53-9

3-amino>-1-propanol

1-methyl-1-<(E)-4-phenyl-3-butenyl>azetidinium trifluoromethanesulfonate
112403-59-5

1-methyl-1-<(E)-4-phenyl-3-butenyl>azetidinium trifluoromethanesulfonate

Conditions
ConditionsYield
With potassium carbonate In dichloromethane at -78 - 23℃;100%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

1-{2-[(3-Hydroxy-propyl)-methyl-amino]-ethyl}-3-phenyl-urea
112403-56-2

1-{2-[(3-Hydroxy-propyl)-methyl-amino]-ethyl}-3-phenyl-urea

Trifluoro-methanesulfonate1-methyl-1-[2-(3-phenyl-ureido)-ethyl]-azetidinium;
112403-65-3

Trifluoro-methanesulfonate1-methyl-1-[2-(3-phenyl-ureido)-ethyl]-azetidinium;

Conditions
ConditionsYield
With potassium carbonate In dichloromethane at -78 - 23℃;100%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

methyl 4-O-(tert-butyldimethylsilyl)-6-deoxy-α-D-allopyranoside 2-acetate
107599-46-2

methyl 4-O-(tert-butyldimethylsilyl)-6-deoxy-α-D-allopyranoside 2-acetate

methyl 4-O-(tert-butyldimethylsilyl)-6-deoxy-α-D-allopyranoside 2-acetate 3-(trifluormethanesulfonate)
107599-47-3

methyl 4-O-(tert-butyldimethylsilyl)-6-deoxy-α-D-allopyranoside 2-acetate 3-(trifluormethanesulfonate)

Conditions
ConditionsYield
With pyridine In dichloromethane at 25℃; for 2h;100%
With pyridine In dichloromethane at -10 - 25℃; for 2h;100%

358-23-6Relevant articles and documents

Dilithium bis[(perfluoroalkyl)sulfonyl]diimide salts as electrolytes for rechargeable lithium batteries

Geiculescu,Xie, Yuan,Rajagopal,Creager,DesMarteau

, p. 1179 - 1185 (2004)

A series of four different dilithium salts of structure F3 CSO2N(Li)SO2-(CF2)x -SO2N(Li)SO2CF3, with x = 2, 4, 6, 8 were synthesized and characterized in polyethylene-oxide-based solid polymer electrolytes. Each salt may be thought of as two bis[(perfluoroalkyl)sulfonyl]imide anions linked together by a perfluoroalkyl chain of a particular length. Taken together, this homologous series provides an opportunity to study the effects of linker chain length and degree of fluorination in dianionic (and ultimately polyanionic) salts on the properties, particularly the conductivity, of the salts in various solvating media. SPEs in polyethylene oxide were characterized using scanning calorimetry, X-ray diffraction, 1H and 19F NMR, and electrochemical impedance spectroscopy for SPEs prepared using ethylene-oxide-oxygen-to-lithium (EO:Li) ratios of 10:1 and 30:1. Trends in SPE ionic conductivity with anion structure revealed an unexpected trend whereby ionic conductivity is generally rising with increased length of the perfluoroalkylene linking group in the dianions. This trend could be the result of a decrease in dianion basicity that results in diminished ion pairing and an enhancement in the number of charge carriers with increasing anion fluorine content, thereby increasing ionic conductivity.

Synthesis of 1,3-dialkyl imidazolium ionic liquids containing difunctional and tetrafunctional perfluoroalkylsulfonyl imide anions

Hickman, Tom,Desmarteau, Darryl D.

, p. 11 - 15 (2012)

Direct methylation of imidazole using methylated difunctional or tetrafunctional perfluorosulfonyl imides renders excellent yields of the corresponding room temperature ionic liquids (RTILs). This methodology provides a simple, halide-free route to several novel RTILs containing multifunctional perfluorosulfonyl imide anions.

Silicon Tetrakis(trifluoromethanesulfonate): A Simple Neutral Silane Acting as a Soft and Hard Lewis Superacid

Driess, Matthias,Hermannsdorfer, André

supporting information, p. 13656 - 13660 (2021/05/03)

A facile synthesis and isolation of pristine silicon tetrakis(trifluoromethanesulfonate), Si(OTf)4, is reported, acting as the first neutral silicon-based Lewis superacid suitable towards soft and hard Lewis bases. Its OTf groups have a dual function: they are excellent leaving groups and modulate the degree of reactivity towards soft and hard Lewis bases. Exposed to soft Lewis donors, Si(OTf)4 leads to [L2Si(OTf)4] complexes (L=isocyanide, thioether and carbonyl compounds) with retention of all Si?OTf bonds. In contrast, it can cleave C?X bonds (X=F, Cl) of hard organic Lewis bases with a high tendency to form SiX4 (X=F, Cl) after halide/triflate exchange. Most notable, Si(OTf)4 allows a gentle oxydefluorination of mono- and bis(trifluoromethyl)benzenes, resulting in the formation of the corresponding benzoylium species, which are stabilized by the weakly coordinating [Si(OTf)6] dianion.

METHOD FOR PRODUCING FLUOROALKANESULFONIC ANHYDRIDE

-

Paragraph 0059-0061, (2014/11/12)

Disclosed is a method for producing a fluoroalkanesulfonic anhydride, which is characterized by that a reaction is conducted while kneading a fluoroalkanesulfonic acid and diphosphorus pentoxide at a temperature that is 40 °C or higher and is lower than 100 °C by using a kneader-type reactor having a maximum power of 1.0 kW or greater per an actual capacity of 100 L and equipped with at least two-shaft blades, that the fluoroalkanesulfonic anhydride to be generated is discharged, and that, while the residue in the reactor after the discharge is kneaded at a temperature that is 100 °C or higher and is lower than 140 °C, the unreacted fluoroalkylsulfonic acid is discharged, recovered and reused as the raw material. It is possible by this method to obtain a fluoroalkanesulfonic anhydride with a high yield.

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