Triflic acid

Triflic acid
Trifluoromethanesulfonic acid
Names
IUPAC name
Trifluoromethanesulfonic acid
Other names
Triflic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.014.625 Edit this at Wikidata
UNII
  • InChI=1S/CHF3O3S/c2-1(3,4)8(5,6)7/h(H,5,6,7) checkY
    Key: ITMCEJHCFYSIIV-UHFFFAOYSA-N checkY
  • InChI=1/CHF3O3S/c2-1(3,4)8(5,6)7/h(H,5,6,7)
    Key: ITMCEJHCFYSIIV-UHFFFAOYAW
  • C(F)(F)(F)S(=O)(=O)O
Properties
CF3SO3H
Molar mass 150.07121 g/mol
Appearance Colorless liquid
Density 1.696 g/mL
Melting point −40 °C (−40 °F; 233 K)
Boiling point 162 °C (324 °F; 435 K)
1600 g/L
Vapor pressure 3.2
Acidity (pKa) −14.7±2.0[1]
Conjugate base Triflate anion
Viscosity 1.864–1.881 mm2/s at 20 °C
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Causes severe acid burns
GHS labelling:
GHS05: Corrosive GHS07: Exclamation mark
Danger
H290, H302, H314, H335, H402
P234, P261, P264, P270, P271, P273, P280, P301+P312+P330, P301+P330+P331, P303+P361+P353, P304+P340+P310, P305+P351+P338+P310, P363, P390, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 0: Will not burn. E.g. waterInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazard ACID: Acid
4
0
2
ACID
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Trifluoromethanesulfonic acid

Triflic acid, the short name for trifluoromethanesulfonic acid, TFMS, TFSA, HOTf or TfOH, is a sulfonic acid with the chemical formula CF3SO3H. It is one of the strongest known acids. Triflic acid is mainly used in research as a catalyst for esterification.[2][3] It is a hygroscopic, colorless, slightly viscous liquid and is soluble in polar solvents.

  1. ^ Trummal, A.; Lipping, L.; Kaljurand, I.; Koppel, I. A.; Leito, I. (2016). "Acidity of Strong Acids in Water and Dimethyl Sulfoxide". Journal of Physical Chemistry A. 120 (20): 3663–3669. Bibcode:2016JPCA..120.3663T. doi:10.1021/acs.jpca.6b02253. PMID 27115918. S2CID 29697201.
  2. ^ Howells, R. D.; McCown, J. D. (1977). "Trifluoromethanesulfonic Acid and Derivatives". Chemical Reviews. 77 (1): 69–92. doi:10.1021/cr60305a005.
  3. ^ Subramanian, L. R.; Martinez, A. G.; Hanack, M.; Prakash, G. K. S.; Hu, J. (2006). "Trifluoromethanesulfonic Acid". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. doi:10.1002/047084289X.rt246.pub2. ISBN 0-471-93623-5.