trifluoromethanesulfonyl trifluoromethanesulfonate

• ChemBase ID: 99630
• Molecular Formular: C2F6O5S2
• Molecular Mass: 282.1388192
• Monoisotopic Mass: 281.90913442
• SMILES: S(=O)(=O)(C(F)(F)F)OS(=O)(=O)C(F)(F)F
• Canonical SMILES: FC(S(=O)(=O)OS(=O)(=O)C(F)(F)F)(F)F
• InChI: InChI=1S/C2F6O5S2/c3-1(4,5)14(9,10)13-15(11,12)2(6,7)8
• InChIKey: WJKHJLXJJJATHN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: trifluoromethanesulfonyl trifluoromethanesulfonate
• IUPAC Traditional name: trifluoromethanesulfonyl trifluoromethanesulfonate; triflic anhydride
• Synonyms: Triflic anhydride; Trifluoromethanesulphonic anhydride 99%; Perfluoromethanesulfonic anhydride solution; Triflic anhydride solution; Trifluoromethanesulfonic anhydride solution; Trifluoromethanesulfonic anhydride; Perfluoromethanesulfonic Anhydride; Tirflic Anhydride; Triflate Anhydride; Triflic Acid Anhydride; Trifluoromethanesulfonic Acid Anhydride; Trifluoromethanesulfonic Anhydride; Trifluoromethylsulfonic Acid Anhydride; Trifluoromethylsulfonic Anhydride; Trifluoromethanesulfonic Anhydride; 三氟甲烷磺酸酐 溶液; 三氟甲磺酸酐 溶液; 三氟甲烷磺酸酐; 三氟甲磺酸酐; 三氟甲烷磺酸酐

Database IDs

• CAS Number: 358-23-6
• EC Number: 206-616-8
• MDL Number: MFCD00000408
• Beilstein Number: 1813600
• PubChem SID: 24889545; 162085893; 24850557
• PubChem CID: 67749

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 2.8943794
• LogD (pH = 7.4): 2.8943794
• Log P: 2.8943794
• Molar Refractivity: 30.1848 cm^3
• Polarizability: 14.092987 Å^3
• Polar Surface Area: 77.51 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -80°C; -80°C
• Boiling Point: 81-83 °C(lit.); 81-83°C; 81-83°C
• Flash Point: none°C
• Density: 1.359 g/mL at 25 °C; 1.677; 1.677 g/mL at 25 °C(lit.); 1.720
• Refractive Index: 1.3210; 1.3212; n20/D 1.321(lit.); n20/D 1.402
• Vapor Pressure: 8 mmHg ( 20 °C)
• Vapor Density: 5.2 (vs air)

Safety Information

• Storage Warning: Corrosive/Harmful/Moisture Sensitive/Store under Argon; Moisture Sensitive
• RTECS: PB2772000
• European Hazard Symbols: Corrosive (C)
• UN Number: 2922; 3265; UN3265
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 14-22-35; 14-22-35-40; 14-34
• Safety Statements: 26-36/37/39-43-45; 26-36/37/39-45; 8-26-30-36/37/39-45-60
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H314; H314-H318; H314-H351
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2922 8/PG 2; UN 3265 8/PG 2
• Supplemental Hazard Statements: Reacts violently with water.
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (T); ≥99%; 95+%; 98%
• Concentration: 1 M in methylene chloride
• Grade: purum
• Linear Formula: (CF3SO2)2O
• Empirical Formula (Hill Notation): C2F6O5S2

DETAILS

Apollo Scientific Ltd - PC7420

Packaged in Safebreak bottles

Sigma Aldrich - 704083

Packaging
25, 100 mL in glass bottle
Application
Catalyst for synthesis of Bacteroides fragilis zwitterionic polysaccharide Ai tetrasaccharide repeating unit via glycosylation1Reagent for stereoselective synthesis of mennosazide methyl uronate donors2Activator for direct glycosylation with anomeric hydroxy sugars3

Sigma Aldrich - 176176

Application
Review of the catalytic application of triflic anhydride, acid and esters to fine chemical and pharmaceutical synthesis.4
Widely used reagent for the synthesis of alkyl and vinyl triflates.
Catalyst for glycosylation for synthesis of polysaccharides1Reagent for stereoselective synthesis of mannosazide methyl uronate donors2Activator for direct glycosylation with anomeric hydroxy sugars3
Packaging
1 kg in glass bottle
50, 250, 500 g in glass bottle
5, 10 g in ampule

Sigma Aldrich - 91737

Other Notes
Electrophilic trifyl source. Reviews4,5,6,7,8
Application
Catalyst for glycosylation for synthesis of polysaccharides1Reagent for stereoselective synthesis of mannosazide methyl uronate donors2Activator for direct glycosylation with anomeric hydroxy sugars3

Toronto Research Chemicals - T790520

Trifluoromethanesulfonic Anhydride is a strong electrophile used in chemical synthesis for introducing the triflyl group.

REFERENCES

• Cai, D. et al.: Org. Synth., 10, 112 (2004)
• For examples of preparation of alkyl and aryl triflates, and use of the latter in the Stille coupling reaction, see: Org. Synth. Coll., 6, 324 (1988); 9, 553 (1998). Alkyl triflates undergo solvolysis reactions between five and seven powers of ten times more rapidly than the corresponding halides or tosylates: J. Am. Chem. Soc., 97, 6478 (1975); Angew. Chem. Int. Ed., 9, 521 (1970). For a review of the chemistry of triflate esters, see: Synthesis, 85 (1982).
• Enolizable carbonyl compounds in the presence of base can be converted to vinyl (enol) triflates: Synthesis, 85 (1982); Org. Synth. Coll., 6, 757 (1988). For conditions employing preferred base, 2,6-Di-tert-butyl-4-methylpyridine, L14143, see: Org. Synth. Coll., 8, 97, 126 (1993). Enol triflates behave as a source of vinyl cations. For reviews, see: Angew. Chem. Int. Ed., 17, 333 (1978); Acc. Chem. Res., 11, 107 (1978); 15, 348 (1982); 21, 147 (1988).
• For formation of keteniminium triflates, see N,N-Dimethylacetamide, A10924.
• The Ritter reaction is normally most successful with tertiary alcohols. In contrast, a useful variation allows conversion of primary or secondary alcohols to amides in good yield: Tetrahedron Lett., 30, 581 (1989):
  
• For use in the Vilsmeier formylation of less active substrates, see N,N-Dimethylformamide, A13547.
• Triflic anhydride has also been found to promote the nitration of arenes, even deactivated ones, under mild conditions: Synthesis, 1087 (1992).
• For a review of chemical transformations induced by the reagent, see: Tetrahedron, 56, 3077 (2000). For a brief feature on uses in synthesis, see: Synlett, 390 (2004).