Trifluoromethanesulfonic acid (CED0006739)

Record Information
Version1.0
Creation Date2026-03-26 22:48:50 UTC
Update Date2026-08-26 00:19:51 UTC
Accession NumberCHEM056619
Identification
Common NameTrifluoromethanesulfonic acid
ClassSmall Molecule
Description
Trifluoromethanesulfonic acid has the chemical formula C1H1F3O3S1 and an average molecular weight of 150.07 g/mol. Trifluoromethanesulfonic acid belongs to the organosulfonic acids and derivatives, a subclass of organic sulfonic acids and derivatives within the organic compounds. The compound has been found in or released from 22 recorded sources. These include aquatic systems and sediments, specifically groundwater, surface water, seawater, and freshwater. It is also present in drinking water and water supply systems, including tap water, bottled water, and desalinated water. Within the wastewater, sanitation, and biosolids sector, it is found in industrial wastewater, wastewater treatment effluent, mine wastewater, and unspecified wastewater. Additionally, it is associated with appliances, HVAC, and refrigerants, such as water coolers and water heaters, as well as building and construction materials, including floors and waterproofing sprays. Marine, shipping, and aquaculture sources include ballast water and bilge water, alongside four other sectors. Recorded routes of exposure for this compound include inhalation, oral intake, and touch.
Contaminant Type
  • PMT
Chemical Structure
Synonyms
ValueSource
1,1,1-Trifluoromethanesulfonic acidChEBI
Acide trifliqueChEBI
Acide trifluoromethanesulfoniqueChEBI
CF3SO3hChEBI
HOTfChEBI
Perfluoromethanesulfonic acidChEBI
TfOHChEBI
TrifluormethansulfonsaeureChEBI
Trifluoromethane sulfonic acidChEBI
Trifluoromethanesulphonic acidChEBI
1,1,1-TrifluoromethanesulfonateGenerator
1,1,1-TrifluoromethanesulphonateGenerator
1,1,1-Trifluoromethanesulphonic acidGenerator
Acide trifluoromethanesulphoniqueGenerator
PerfluoromethanesulfonateGenerator
PerfluoromethanesulphonateGenerator
Perfluoromethanesulphonic acidGenerator
TrifluormethansulphonsaeureGenerator
Trifluoromethane sulfonateGenerator
Trifluoromethane sulphonateGenerator
Trifluoromethane sulphonic acidGenerator
TrifluoromethanesulfonateGenerator
TrifluoromethanesulphonateGenerator
1,1,1-Trifluoro-methanesulfonic acidHMDB
2794-60-7 (Barium salt)HMDB
2923-28-6 (Silver(+1) salt))HMDB
CF3-SO3hHMDB
Fluorad FC24HMDB
Methanesulfonic acid, trifluoro- (6ci,7ci,8ci,9ci)HMDB
TFSHMDB
Triflic acidHMDB
Trifluoro-methanesulfonic acidHMDB
Trifluoromethylsulfonic acidHMDB
TrimsylateHMDB
Trifluoromethanesulfonic acidGenerator
TriflateGenerator
AgOTf CPDMeSH
In(otf)3MeSH
Aluminum triflateMeSH
Cerium triflateMeSH
Indium triflateMeSH
Silver trifluoromethanesulfonateMeSH
Trifluoromethanesulfonic acid, cupric saltMeSH
Trifluoromethanesulfonic acid, indium saltMeSH
Eu(otf)3MeSH
Silver triflateMeSH
Trifluoromethanesulfonic acid, barium saltMeSH
Trifluoromethanesulfonic acid, cerium (+3) saltMeSH
Trifluoromethanesulfonic acid, lithium saltMeSH
Trifluoromethanesulfonic acid, samarium saltMeSH
Zinc triflateMeSH
As(otf)2MeSH
TFMSA CPDMeSH
Al(otf)3MeSH
Cu(otf)2MeSH
Cupric trifluoromethanesulfonateMeSH
Mercury(II) trifluoromethanesulfonateMeSH
Samarium triflateMeSH
Trifluoromethanesulfonic acid, aluminum saltMeSH
Trifluoromethanesulfonic acid, lanthanum (+3) saltMeSH
Trifluoromethanesulfonic acid, silver (+1) saltMeSH
Trifluoromethanesulfonic acid, zinc saltMeSH
Chemical FormulaC1H1F3O3S1
Average Molecular Mass150.070 g/mol
Monoisotopic Mass149.960 g/mol
CAS Registry Number1493-13-6;132645-03-5;146819-41-2;410094-25-6;686276-05-1;83936-79-2
IUPAC Nametrifluoromethanesulfonic acid
Traditional Nametrifluoromethanesulfonic acid
SMILESOS(=O)(=O)C(F)(F)F
InChI IdentifierInChI=1S/CHF3O3S/c2-1(3,4)8(5,6)7/h(H,5,6,7)
InChI KeyITMCEJHCFYSIIV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as trifluoromethanesulfonates. These are alkanesulfonic acids, that contain a sulfonate group that is substituted with a trifluoromethyl group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic sulfonic acids and derivatives
Sub ClassOrganosulfonic acids and derivatives
Direct ParentTrifluoromethanesulfonates
Alternative Parents
Substituents
  • Trifluoromethanesulfonate
  • Sulfonyl
  • Organosulfonic acid
  • Methanesulfonate
  • Trihalomethane
  • Organic oxygen compound
  • Organic oxide
  • Halomethane
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organofluoride
  • Organohalogen compound
  • Alkyl halide
  • Alkyl fluoride
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.15 g/LALOGPS
logP0.6ALOGPS
logP1.15ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)-3.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity16.98 m³·mol⁻¹ChemAxon
Polarizability7.78 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-015a-9600000000-745bd12556d68fe09a96Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ue9-1900000000-c3301e5444240de63268Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0900000000-cc607981f759ba64eee1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9600000000-bb55859234774f7eea68Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0900000000-57a7a9d43708bf39d582Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kb-5900000000-263972a1c0395d8277a9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-2900000000-0fbd71972ee7cb1208d4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0900000000-480c2184178a6af8d70bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0900000000-480c2184178a6af8d70bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0900000000-480c2184178a6af8d70bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-d7b71876de767050a2b2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-d7b71876de767050a2b2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0gc0-9200000000-29460f0b2e767d0055e1Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity ValuesNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
3Irrigation waterAgriculture & land managementNot Available
27Water CoolersAppliances, HVAC & refrigerantsNot Available
43Water heatersAppliances, HVAC & refrigerantsNot Available
50GroundwaterAquatic systems & sedimentsNot Available
51Surface waterAquatic systems & sedimentsNot Available
52SeawaterAquatic systems & sedimentsNot Available
53FreshwaterAquatic systems & sedimentsNot Available
70Stormwater runoffAutomotive & urban infrastructureNot Available
88Waterproofing spraysBuilding & ConstructionNot Available
115Drinking waterDrinking water & water supplyNot Available
116Tap waterDrinking water & water supplyNot Available
117Bottled waterDrinking water & water supplyNot Available
118Desalinated waterDrinking water & water supplyNot Available
181Ballast waterMarine, shipping & aquacultureNot Available
182Bilge waterMarine, shipping & aquacultureNot Available
468Industrial wastewaterWastewater, sanitation & biosolidsNot Available
470Wastewater treatment effluentWastewater, sanitation & biosolidsNot Available
475Mine wastewaterWastewater, sanitation & biosolidsNot Available
477Wastewater, unspecifiedWastewater, sanitation & biosolidsNot Available
494Food contact materialsFood, food processing & cookwareNot Available
497FloorsBuilding & ConstructionNot Available
506AntennasElectrical & Electronic EquipmentNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)383.485
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)323.308
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)192.443
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)1261.62
Carbonic anhydrase 6 structureClick to view 3D structureCarbonic anhydrase 6P23280HumansPredicted (SEA)706.482
Carbonic anhydrase 4 structureClick to view 3D structureCarbonic anhydrase 4P22748HumansPredicted (SEA)943.844
Click to view 3D structureCarbonic anhydrase 2P00921Bos taurusPredicted (SEA)163.561
Click to view 3D structureAlpha carbonic anhydraseB5SU02Stylophora pistillataPredicted (SEA)171.035
Click to view 3D structureCarbonic anhydraseC0IX24Stylophora pistillataPredicted (SEA)170.957
Click to view 3D structureCarbonic anhydraseP40881Methanosarcina thermophilaPredicted (SEA)103.15
Click to view 3D structureCarbonic anhydrase 5A, mitochondrialP35218HumansPredicted (SEA)2155.72
Carbonic anhydrase 13 structureClick to view 3D structureCarbonic anhydrase 13Q8N1Q1HumansPredicted (SEA)1574.89
Liver carboxylesterase 1 structureClick to view 3D structureLiver carboxylesterase 1P23141HumansPredicted (SEA)801.769
Click to view 3D structureLiver carboxylesterase B-1Q63010Rattus norvegicusPredicted (SEA)19.3066
Click to view 3D structureLiver carboxylesteraseQ29550Sus scrofaPredicted (SEA)290.144
Click to view 3D structure7-dehydrocholesterol reductaseQ9Z2Z8Rattus norvegicusPredicted (SEA)9.18621
Click to view 3D structureAcetylpolyamine amidohydrolaseQ48935Mycoplana ramosaPredicted (SEA)18.5281
Click to view 3D structurePhosphoglycerate kinaseP00560Saccharomyces cerevisiae S288cPredicted (SEA)3.73676
Click to view 3D structureAspartate-semialdehyde dehydrogenaseO25801Helicobacter pylori (strain ATCC 700392 / 26695) (Campylobacterpylori)Predicted (SEA)14.6357
Carbonic anhydrase 14 structureClick to view 3D structureCarbonic anhydrase 14Q9ULX7HumansPredicted (SEA)4952.22
Click to view 3D structureCarbonic anhydrase 5B, mitochondrialQ9Y2D0HumansPredicted (SEA)4474.07
Click to view 3D structureCarbonic anhydrase 4Q95323Bos taurusPredicted (SEA)2081.92
Click to view 3D structureJuvenile hormone esteraseQ9GPG0Manduca sextaPredicted (SEA)63.0579
Click to view 3D structureCocaine esteraseO00748HumansPredicted (SEA)2082.78
Click to view 3D structureFatty-acid amide hydrolase 1O00519HumansPredicted (SEA)6148.06
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0036577
FooDB IDFDB015485
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDTFS
Wikipedia LinkTrifluoromethanesulfonic acid
Chemspider ID56192
ChEBI ID48511
PubChem Compound ID62406
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Sheets MR, Li A, Bower EA, Weigel AR, Abbott MP, Gallo RM, Mitton AA, Klumpp DA: Superelectrophilic chemistry of imidazoles. J Org Chem. 2009 Mar 20;74(6):2502-7. doi: 10.1021/jo802798x.
2. Saito A, Hyodo N, Hanzawa Y: Synthesis of highly substituted oxazoles through iodine(III)-mediated reactions of ketones with nitriles. Molecules. 2012 Sep 13;17(9):11046-55. doi: 10.3390/molecules170911046.
3. Sagarik K, Phonyiem M, Lao-ngam C, Chaiwongwattana S: Mechanisms of proton transfer in Nafion: elementary reactions at the sulfonic acid groups. Phys Chem Chem Phys. 2008 Apr 21;10(15):2098-112. doi: 10.1039/b718480h. Epub 2008 Feb 21.
4. Zhu YP, Jia FC, Liu MC, Wu LM, Cai Q, Gao Y, Wu AX: I2-CF3SO3H synergistic promoted sp3 C-H bond diarylation of aromatic ketones. Org Lett. 2012 Oct 19;14(20):5378-81. doi: 10.1021/ol302613q. Epub 2012 Oct 11.
5. Yamada K, Fujita H, Kunishima M: A novel acid-catalyzed O-benzylating reagent with the smallest unit of imidate structure. Org Lett. 2012 Oct 5;14(19):5026-9. doi: 10.1021/ol302222p. Epub 2012 Sep 20.
6. Iwasaki T, Nagaki A, Yoshida J: Microsystem controlled cationic polymerization of vinyl ethers initiated by CF3SO3H. Chem Commun (Camb). 2007 Mar 28;(12):1263-5. Epub 2007 Jan 11.
7. Wang K, Tan LL, Chen DX, Song N, Xi G, Zhang SX, Li C, Yang YW: One-pot synthesis of pillar[n]arenes catalyzed by a minimum amount of TfOH and a solution-phase mechanistic study. Org Biomol Chem. 2012 Dec 21;10(47):9405-9. doi: 10.1039/c2ob26635k. Epub 2012 Oct 30.
8. Zhang Y, Briski J, Zhang Y, Rendy R, Klumpp DA: Superacid-catalyzed reactions of olefinic pyrazines: an example of anti-Markovnikov addition involving superelectrophiles. Org Lett. 2005 Jun 9;7(12):2505-8.
9. Xu W, Dolbier WR Jr, Salazar J: Ionic liquid, surrogate hydrogen bromide reagent for ring opening of cyclopropyl ketones. J Org Chem. 2008 May 2;73(9):3535-8. doi: 10.1021/jo800337t. Epub 2008 Apr 5.
10. Park JH, Park CY, Song HS, Huh YS, Kim GH, Park CP: Green diacetoxylation of alkenes in a microchemical system. Org Lett. 2013 Feb 15;15(4):752-5. doi: 10.1021/ol3026445. Epub 2013 Jan 31.
11. Franken A, McGrath TD, Stone FG: Ten-vertex iron-monocarbollide complexes: synthesis and reactivity of the anion [4,9-{Fe(CO)4}-9,9,9-(CO)3-arachno-9,6-FeCB8H11]-. Inorg Chem. 2006 Mar 20;45(6):2669-77.
12. Pina F, Passaniti P, Maestri M, Balzani V, Vogtle F, Gorka M, Lee SK, van Heyst J, Fakhrnabavi H: Ground and excited-state electronic interactions in poly(propylene amine) dendrimers functionalized with naphthyl units: effect of protonation and metal complexation. Chemphyschem. 2004 Apr 19;5(4):473-80.
13. Muto Y, Murai Y, Sakihama Y, Hashidoko Y, Hashimoto M: Effective Friedel-Crafts acylation of biotin acid chloride in trifluoromethanesulfonic acid. Biosci Biotechnol Biochem. 2012;76(11):2162-4. Epub 2012 Nov 7.
14. Ilg K, Werner H: Reactions of the allenylidenes trans-[IrCl[=C=C=C(ph)R](PiPr3)2] with electrophiles: generation of butatriene-, carbene-, and carbyne- iridium complexes. Chemistry. 2001 Nov 5;7(21):4633-9.
15. Zong R, Thummel RP: A new family of Ru complexes for water oxidation. J Am Chem Soc. 2005 Sep 21;127(37):12802-3.
16. Plazuk D, Zakrzewski J: Friedel-Crafts type reaction of ferrocene with beta-ketoesters. J Org Chem. 2002 Nov 29;67(24):8672-4.
17. Li A, Gilbert TM, Klumpp DA: Preparation of aza-polycyclic aromatic compounds via superelectrophilic cyclizations. J Org Chem. 2008 May 2;73(9):3654-7. doi: 10.1021/jo8003474. Epub 2008 Apr 1.
18. Brorson M, Hazell A, Jacobsen CJ, Schmidt I, Villadsen J: Preparation and crystal structures of formato complexes of the [MIV3O4]4+ and [MIV3S4]4+ (M = Mo, W) clusters. Convenient precursors to the corresponding aqua complexes. Inorg Chem. 2000 Apr 3;39(7):1346-50.
19. Ajaz A, McLaughlin EC, Skraba SL, Thamatam R, Johnson RP: Phenyl shifts in substituted arenes via ipso arenium ions. J Org Chem. 2012 Nov 2;77(21):9487-95. doi: 10.1021/jo301848g. Epub 2012 Oct 17.
20. Cherian AE, Domski GJ, Rose JM, Lobkovsky EB, Coates GW: Acid-catalyzed ortho-alkylation of anilines with styrenes: an improved route to chiral anilines with bulky substituents. Org Lett. 2005 Nov 10;7(23):5135-7.
21. Bonnot C, Chambron JC, Espinosa E, Bernauer K, Scholten U, Graff R: The proton complex of a diaza-macropentacycle: structure, slow formation, and chirality induction by ion pairing with the optically active 1,1'-binaphthyl-2,2'-diyl phosphate anion. J Org Chem. 2008 Oct 17;73(20):7871-81. doi: 10.1021/jo801438d. Epub 2008 Sep 24.
22. Ohkuma T, Utsumi N, Tsutsumi K, Murata K, Sandoval C, Noyori R: The hydrogenation/transfer hydrogenation network: asymmetric hydrogenation of ketones with chiral eta6-arene/N-Tosylethylenediamine-ruthenium(II) catalysts. J Am Chem Soc. 2006 Jul 12;128(27):8724-5.
23. Hitchcock PB, Hu J, Lappert MF, Severn JR: Synthesis and structures of beta-diketiminatotin(II) halides, an amide and of Sn(=E)[{N(R)C(Ph)}2CH](NR2) (E = S or Se, R = SiMe3). Dalton Trans. 2004 Dec 21;(24):4193-201. Epub 2004 Nov 16.
24. Koizumi T, Harada K, Asahara H, Mochizuki E, Kokubo K, Oshima T: Acid-catalyzed transannular cyclization of 3aH-cyclopentene[8]annulene-1,4-(5H,9aH)-diones and some proposed mechanisms. J Org Chem. 2005 Oct 14;70(21):8364-71.
25. Eom D, Park S, Park Y, Ryu T, Lee PH: Synthesis of indenes via Bronsted acid catalyzed cyclization of diaryl- and alkyl aryl-1,3-dienes. Org Lett. 2012 Nov 2;14(21):5392-5. doi: 10.1021/ol302271w. Epub 2012 Oct 24.
26. Kanzaki R, Doi H, Song X, Hara S, Ishiguro S, Umebayashi Y: Acid-base property of N-methylimidazolium-based protic ionic liquids depending on anion. J Phys Chem B. 2012 Dec 6;116(48):14146-52. doi: 10.1021/jp308477p. Epub 2012 Nov 20.
27. Sai KK, Gilbert TM, Klumpp DA: Knorr cyclizations and distonic superelectrophiles. J Org Chem. 2007 Dec 7;72(25):9761-4. Epub 2007 Nov 14.
28. Kurouchi H, Kawamoto K, Sugimoto H, Nakamura S, Otani Y, Ohwada T: Activation of electrophilicity of stable Y-delocalized carbamate cations in intramolecular aromatic substitution reaction: evidence for formation of diprotonated carbamates leading to generation of isocyanates. J Org Chem. 2012 Oct 19;77(20):9313-28. doi: 10.1021/jo3020566. Epub 2012 Oct 10.
29. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.