Pyridinium p-toluenesulfonate

Names
IUPAC name

4-methylbenzenesulfonate; pyridin-1-ium

Other names

pyridinium p-toluenesulfonate, pyridinium tosylate

Identifiers

CAS Number

* 24057-28-1 Y

3D model (JSmol)

* Interactive image

Abbreviations  | PPTS
ChemSpider |

* 141806 Y

PubChem CID

* 466102

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 Y

Key: ZDYVRSLAEXCVBX-UHFFFAOYSA-N Y

* 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

Key: ZDYVRSLAEXCVBX-UHFFFAOYAE

SMILES

* CC1=CC=C(S(=O)([O-])=O)C=C1.C2=[NH+]C=CC=C2

Properties

Chemical formula

| C12H13NO3S
Molar mass | 251.30 g·mol−1
Appearance  | Colourless 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).

Y verify (what is YN ?)
Infobox references

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). http://evans.rc.fas.harvard.edu/pdf/evans_pKa_table.pdf. Retrieved 2016-03-02.
2. ↑ TOKYO CHEMICAL INDUSTRY CO., LTD. "Pyridinium p-Toluenesulfonate". http://www.tokyokasei.co.jp/catalog/P0942.html. Retrieved 2011-09-16.

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*[CID]: Compound ID