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Triflic acid information


Triflic acid
Trifluoromethanesulfonic acid
Names
IUPAC name
Trifluoromethanesulfonic acid
Other names
Triflic acid
Identifiers
CAS Number
  • 1493-13-6 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:48511 checkY
ChemSpider
  • 56192 checkY
ECHA InfoCard 100.014.625 Edit this at Wikidata
PubChem CID
  • 62406
UNII
  • JE2SY203E8 checkY
CompTox Dashboard (EPA)
  • DTXSID70892979 DTXSID2044397, DTXSID70892979 Edit this at Wikidata
InChI
  • 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
SMILES
  • C(F)(F)(F)S(=O)(=O)O
Properties
Chemical formula
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)
Solubility in water
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:
Pictograms
GHS05: Corrosive GHS07: Exclamation mark
Signal word
Danger
Hazard statements
H290, H302, H314, H335, H402
Precautionary statements
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).
checkY verify (what is checkY☒N ?)
Infobox references
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.

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Triflic acid

Last Update:

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...

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Fluoroantimonic acid

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> H0 > −28) Magic acid (H0 = −23) Carborane acid (H0 < −18) Fluorosulfuric acid (H0 = −15) Triflic acid (H0 = −15) Perchloric acid (H0 = −13) Of the above...

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Trifluoromethanesulfonic anhydride

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Tf2O, triflic anhydride is the acid anhydride of the superacid triflic acid, CF3SO2OH. Triflic anhydride is prepared by dehydration of triflic acid using...

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Superacid

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2-dichloroethane in comparison to triflic acid) Fluorosulfuric acid (FSO3H, H0 = −15.1) Hydrogen fluoride (HF, H0 = −15.1) Triflic acid (HOSO2CF3, H0 = −14.9) Oleum...

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Carborane acid

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exceed that of triflic acid, CF 3SO 3H, and bistriflimide, (CF 3SO 2) 2NH, compounds previously regarded as the strongest isolable acids. Their high acidities...

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Triflate

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the fact that triflic acid (CF3SO3H) is a superacid; i.e. it is more acidic than pure sulfuric acid, already one of the strongest acids known. A triflate...

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Methyl trifluoromethanesulfonate

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with triflic acid. CF3SO2OH + (CH3O)2SO2 → CF3SO2OCH3 + CH3OSO2OH Upon contact with water, methyl triflate loses its methyl group, forming triflic acid and...

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Bistriflimide

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6-trinitrophenol (picric acid), anchored to zero to crudely approximate the aqueous pKa scale), making it more acidic than triflic acid (pKaMeCN = 0.70, pKaDCE(relative...

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Acid strength

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Acid strength is the tendency of an acid, symbolised by the chemical formula HA {\displaystyle {\ce {HA}}} , to dissociate into a proton, H + {\displaystyle...

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Triflidic acid

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is estimated to have an acidity 104 times that of triflic acid (pKaaq ~ –14), as measured by its acid dissociation constant. It was first prepared in 1987...

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Fluorosulfuric acid

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HSO3F hydrolyzes slowly to hydrogen fluoride (HF) and sulfuric acid. The related triflic acid (CF3SO3H) retains the high acidity of HSO3F but is more hydrolytically...

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Perfluorinated compound

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the simplest perfluorinated nitrile. Triflic acid, a useful strong acid perfluorobutanesulfonic acid (PFBS) used as a replacement for PFOS in 3M's...

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Organofluorine chemistry

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reagents of value beyond organofluorine chemistry. Triflic acid (CF3SO3H) and trifluoroacetic acid (CF3CO2H) are useful throughout organic synthesis....

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Strong electrolyte

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acid, FSO3HSbF5 Carborane superacid, H(CHB11Cl11) Fluorosulfuric acid, FSO3H Triflic acid, CF3SO3H Strong bases Lithium hydroxide, LiOH Sodium hydroxide...

Word Count : 369

Brosyl group

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p-bromophenylsulfonic acid. The term brosylate refers to the anion of p-bromophenylsulfonic acid (BrC6H4SO3−). Tosyl group Tosylic acid Triflic acid Sulfonyl group...

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Acid

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p-Toluenesulfonic acid (or tosylic acid, CH3C6H4SO3H) Trifluoromethanesulfonic acid (or triflic acid, CF3SO3H) Polystyrene sulfonic acid (sulfonated polystyrene...

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CBS catalyst

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reagent 3c and proline ester 3b. A Lewis acid superacid salt (6) can be obtained with the aid of triflic acid (5). Many other such catalysts exist with...

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Fluoroboric acid

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Fluoroboric acid or tetrafluoroboric acid (archaically, fluoboric acid) is an inorganic compound with the simplified chemical formula H+[BF4]−. Solvent-free...

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Trimethylsilyl group

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to silyl enol ether by reaction with tris(trimethylsilyl)silane and triflic acid with evolution of hydrogen. The aldol reaction is catalyzed by...

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List of copper salts

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(thiocyanic acid) Copper(II) triflate Cu(OSO2CF3)2 Triflate (triflic acid) Copper(II) tetrafluoroborate Cu(BF4)2 Tetrafluoroborate (tetrafluoroboric acid) Copper(II)...

Word Count : 101

Scandium oxide

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into hydrated scandium(III) triflate (Sc(OTf)3·nH2O) by a reaction with triflic acid. Metallic scandium is produced industrially by the reduction of scandium...

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Knorr quinoline synthesis

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superelectrophile) over the N,O dicationic intermediate . For preparative purposes triflic acid is recommended: Synthetische Versuche mit dem Acetessigester Justus Liebig's...

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Thionyl chloride

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sulfinic acid. Both aryl sulfinyl chlorides and diaryl sulfoxides can be prepared from arenes through reaction with thionyl chloride in triflic acid or the...

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Angarsk Electrochemical Combine

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The Angarsk Electrochemical Combine manufactures uranium hexafluoride, triflic acid, niobium oxide, tantalum oxide, radiation detectors, automated personnel...

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Photoacid

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ultimate products are thus a neutral organic sulfide and the strong acid triflic acid. [(C6H5)3S+][CF3SO− 3] + hν → [(C6H5)2S+.][CF3SO− 3] + C6H. 5 [(C6H5)2S+...

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Strychnine total synthesis

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double bond isomerization (sodium / iPrOH), Boc group deprotection (triflic acid) and amine alkylation with (Z)-BrCH2CICH=CH2OTBDMS (see Rawal) gave compound...

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Boranylium ions

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protonated by various acids to make borenium ions. This synthetic method was developed in 1983 by Narula and Noth who used triflic acid to protonate 1...

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