pyridin-1-ium 4-methylbenzene-1-sulfonate

• ChemBase ID: 129195
• Molecular Formular: C12H13NO3S
• Molecular Mass: 251.30152
• Monoisotopic Mass: 251.06161428
• SMILES: Cc1ccc(cc1)S(=O)(=O)[O-].c1cc[nH+]cc1
• Canonical SMILES: c1ccc[nH+]c1.Cc1ccc(cc1)S(=O)(=O)[O-]
• InChI: InChI=1S/C7H8O3S.C5H5N/c1-6-2-4-7(5-3-6)11(8,9)10;1-2-4-6-5-3-1/h2-5H,1H3,(H,8,9,10);1-5H
• InChIKey: ZDYVRSLAEXCVBX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: pyridin-1-ium 4-methylbenzene-1-sulfonate
• IUPAC Traditional name: pyridium tosylate
• Synonyms: pyridinium p-toluenesulfonate; Pyridinium p-toluenesulfonate; PPTS; Pyridinium tosylate; Pyridinium p-toluenesulfonate; 对甲苯磺酸吡啶鎓

Database IDs

• CAS Number: 24057-28-1
• EC Number: 246-002-7
• MDL Number: MFCD00013108
• Beilstein Number: 3764305
• PubChem SID: 162223492
• PubChem CID: 466102
• Chemspider ID: 141806
• Wikipedia Title: Pyridinium_p-toluenesulfonate

CALCULATED PROPERTIES

• Acid pKa: -2.1372879
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -0.7088225
• LogD (pH = 7.4): -0.7088248
• Log P: 1.6675739
• Molar Refractivity: 40.6 cm^3
• Polarizability: 16.615282 Å^3
• Polar Surface Area: 57.2 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Colourless solid
• Melting Point: 116-120°C; 120°C (source)
• pKa: 5.21

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Irritant (Xi)
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A

Product Information

• Purity: 98%; 98+%

REFERENCES

• Mild catalyst for the formation of THP derivatives of alcohols superior to p-toluenesulfonic acid, where acid-sensitive functionality is present. Similarly, the reagent has been used for deprotection of THP ethers in ethanol: J. Org. Chem., 42. 3772 (1977).
• This application has been extended to other acetalization or trans-acetalization reactions, where more acidic conditions are undesirable: Synthesis, 724 (1979).
• For use in cleavage of TBDMS protecting groups, see: J. Chem. Soc. Perkin 1, 169 (1993).