8/23/2021

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Pyridinium p-toluenesulfonate
Names
IUPAC name
Other names
pyridinium p-toluenesulfonate
Identifiers
  • 24057-28-1
AbbreviationsPPTS
ChemSpider
ECHA InfoCard
PubChemCID
CompTox Dashboard(EPA)
  • 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
  • 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);1-5H
  • CC1=CC=C(S(=O)([O-])=O)C=C1.C2=[NH+]C=CC=C2
Properties
C12H13NO3S
Molar mass251.30 g·mol−1
AppearanceColourless solid
Melting point 120 °C (248 °F; 393 K) source[2]
Acidity (pKa)5.21[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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

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Uses[edit]

Phlebotomy

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[edit]

  1. ^David A. Evans (2005-11-04). 'Evans pKa Table'(PDF). Retrieved 2016-03-02.
  2. ^TOKYO CHEMICAL INDUSTRY CO., LTD. 'Pyridinium p-Toluenesulfonate'. Retrieved 2011-09-16.
Retrieved from 'https://en.wikipedia.org/w/index.php?title=Pyridinium_p-toluenesulfonate&oldid=911135581'

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