Misplaced Pages

Pyridinium p-toluenesulfonate

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Pyridinium p-toluenesulfonate
Names
IUPAC name 4-methylbenzenesulfonate; pyridin-1-ium
Other names pyridinium p-toluenesulfonate
Identifiers
CAS Number
3D model (JSmol)
Abbreviations PPTS
ChemSpider
ECHA InfoCard 100.041.806 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
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);1-5HKey: ZDYVRSLAEXCVBX-UHFFFAOYSA-N
  • InChI=1/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);1-5HKey: ZDYVRSLAEXCVBX-UHFFFAOYAE
SMILES
  • CC1=CC=C(S(=O)()=O)C=C1.C2=C=CC=C2
Properties
Chemical formula C12H13NO3S
Molar mass 251.30 g·mol
Appearance Colourless solid
Melting point 120 °C (248 °F; 393 K) source
Acidity (pKa) 5.21
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Pyridinium p-toluenesulfonate (PPTS) is a colourless solid salt of pyridine and p-toluenesulfonic acid.

Uses

In organic synthesis, PPTS is used as a weakly acidic catalyst, providing an organic soluble source of pyridinium (C5H5NH) ions. For example, PPTS is used to deprotect silyl ethers or tetrahydropyranyl ethers when a substrate is unstable to stronger acid catalysts. It is also a commonly used catalyst for the preparation of acetals and ketals from aldehydes and ketones.

References

  1. David A. Evans (2005-11-04). "Evans pKa Table" (PDF). Retrieved 2016-03-02.
  2. TOKYO CHEMICAL INDUSTRY CO., LTD. "Pyridinium p-Toluenesulfonate". Archived from the original on 2012-04-02. Retrieved 2011-09-16.
Categories: