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Key Documents

8.18043

Sigma-Aldrich

Trifluoromethanesulfonic anhydride

for synthesis

Synonym(s):

Trifluoromethanesulfonic anhydride

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About This Item

Linear Formula:
(CF3SO2)2O
CAS Number:
358-23-6
Molecular Weight:
282.14
MDL number:
MFCD00000408
UNSPSC Code:
12352106
EC Index Number:
206-616-8
NACRES:
NA.22

Quality Level

200

Assay

≥99.0% (acidimetric)

form

liquid

potency

1012 mg/kg LD50, oral (Rat)

density

1.71 g/cm3 at 20 °C

storage temp.

2-30°C

InChI

1S/C2F6O5S2/c3-1(4,5)14(9,10)13-15(11,12)2(6,7)8

InChI key

WJKHJLXJJJATHN-UHFFFAOYSA-N

Application

  • Electrophilic activation using trifluoromethanesulfonic anhydride: This method is utilized for transformations of amides, sulfoxides, and phosphorus oxides through nucleophilic trapping, highlighting its versatility in organic synthesis (Huang and Kang, 2022).
  • Triflic anhydride in organic synthesis: A comprehensive review of triflic anhydride′s roles, focusing on its application across various organic transformations (Qin, Cheng, and Jiao, 2023).
  • Synthesis of nitriles: Employing trifluoromethanesulfonic anhydride for converting aldoximes to nitriles under mild conditions, showcasing an innovative application in nitrile synthesis (Uludag, 2020).
  • Hydrotrifluoromethylthiolation of alkenes: Uses trifluoromethanesulfonic anhydride for the hydrotrifluoromethylthiolation of unactivated alkenes and alkynes, expanding the utility of this reagent in radical reactions (Ouyang, Xu, and Qing, 2019).
  • Low-cost trifluoromethylation reagent: Discusses the economic benefits and wide-ranging applications of trifluoromethanesulfonic anhydride in trifluoromethylation processes (Ouyang, Xu, and Qing, 2018).

Analysis Note

Assay (acidimetric): ≥ 99.0 %
Density (d 20 °C/ 4 °C): 1.715 - 1.720
Identity (IR): passes test

Signal Word

Danger

Hazard Statements

H272 - H302 - H314 - H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Ox. Liq. 2 - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

5.1B - Oxidizing hazardous materials

WGK

WGK 3

Flash Point(F)

not determined

Flash Point(C)

not determined

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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