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Showing NP-Card for Trifluoromethanesulfonic acid (NP0337896)

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Record Information
Version2.0
Created at2024-09-11 12:56:03 UTC
Updated at2024-09-11 12:56:03 UTC
NP-MRD IDNP0337896
Secondary Accession NumbersNone
Natural Product Identification
Common NameTrifluoromethanesulfonic acid
DescriptionTrifluoromethanesulfonic acid, also known as 1,1,1-trifluoromethanesulfonate or acide trifluoromethanesulfonique, 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. Trifluoromethanesulfonic acid is an extremely strong acidic compound (based on its pKa). Trifluoromethanesulfonic acid was first documented in 2008 (PMID: 18688364). A one-carbon compound that is methanesulfonic acid in which the hydrogens attached to the methyl carbon have been replaced by fluorines (PMID: 19215114) (PMID: 22976468) (PMID: 23057842) (PMID: 22994426).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0337896 (Trifluoromethanesulfonic acid)


  Mrv0541 05061309122D          

  8  7  0  0  0  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.8250    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8250    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  1  1  0  0  0  0
  8  1  1  0  0  0  0
  8  5  1  0  0  0  0
  8  6  2  0  0  0  0
  8  7  2  0  0  0  0
M  END
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3D MOL for NP0337896 (Trifluoromethanesulfonic acid)

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3D SDF for NP0337896 (Trifluoromethanesulfonic acid)

  Mrv0541 05061309122D          

  8  7  0  0  0  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.8250    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8250    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  1  1  0  0  0  0
  8  1  1  0  0  0  0
  8  5  1  0  0  0  0
  8  6  2  0  0  0  0
  8  7  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0337896

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OS(=O)(=O)C(F)(F)F

> <INCHI_IDENTIFIER>
InChI=1S/CHF3O3S/c2-1(3,4)8(5,6)7/h(H,5,6,7)

> <INCHI_KEY>
ITMCEJHCFYSIIV-UHFFFAOYSA-N

> <FORMULA>
CHF3O3S

> <MOLECULAR_WEIGHT>
150.077

> <EXACT_MASS>
149.959849203

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
7.781351905453912

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
trifluoromethanesulfonic acid

> <ALOGPS_LOGP>
0.60

> <JCHEM_LOGP>
1.148037056

> <ALOGPS_LOGS>
-1.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.4301211369712297

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
16.9819

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.15e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trifluoromethanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0337896 (Trifluoromethanesulfonic acid)
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PDB for NP0337896 (Trifluoromethanesulfonic acid)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    2  F   UNK     0       0.000   3.080   0.000  0.00  0.00           F+0
HETATM    3  F   UNK     0      -1.540   1.540   0.000  0.00  0.00           F+0
HETATM    4  F   UNK     0       1.540   1.540   0.000  0.00  0.00           F+0
HETATM    5  O   UNK     0       0.000  -1.540   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -1.540   0.000   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.540   0.000   0.000  0.00  0.00           O+0
HETATM    8  S   UNK     0       0.000   0.000   0.000  0.00  0.00           S+0
CONECT    1    2    3    4    8                                             
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    8                                                            
CONECT    6    8                                                            
CONECT    7    8                                                            
CONECT    8    1    5    6    7                                             
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END

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3D PDB for NP0337896 (Trifluoromethanesulfonic acid)
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SMILES for NP0337896 (Trifluoromethanesulfonic acid)
OS(=O)(=O)C(F)(F)F
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INCHI for NP0337896 (Trifluoromethanesulfonic acid)
InChI=1S/CHF3O3S/c2-1(3,4)8(5,6)7/h(H,5,6,7)
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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 FormulaCHF3O3S
Average Mass150.0770 Da
Monoisotopic Mass149.95985 Da
IUPAC Nametrifluoromethanesulfonic acid
Traditional Nametrifluoromethanesulfonic acid
CAS Registry NumberNot Available
SMILES
OS(=O)(=O)C(F)(F)F
InChI Identifier
InChI=1S/CHF3O3S/c2-1(3,4)8(5,6)7/h(H,5,6,7)
InChI KeyITMCEJHCFYSIIV-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
HMDB IDHMDB0036577  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB015485  
KNApSAcK IDNot Available
Chemspider ID56192  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTrifluoromethanesulfonic acid  
METLIN IDNot Available
PubChem Compound62406  
PDB IDTFS  
ChEBI ID48511  
Good Scents IDNot Available
References
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. [PubMed:19215114  ] 
  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. [PubMed:22976468  ] 
  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. [PubMed:18688364  ] 
  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. [PubMed:23057842  ] 
  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. [PubMed:22994426  ]