Pyridinium p-toluenesulfonate

Pyridinium p-toluenesulfonate
Names

IUPAC name 4-methylbenzenesulfonate; pyridin-1-ium
Other names pyridinium p-toluenesulfonate
Identifiers
CAS Number	24057-28-1^Y
Abbreviations	PPTS
ChemSpider	141806^Y
Jmol interactive 3D	Image
PubChem	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 Cc1ccc(cc1)S(=O)(=O)[O-].c1cc[nH+]cc1
Properties
Chemical formula	C₁₂H₁₃NO₃S
Molar mass	251.30 g·mol⁻¹
Appearance	Colourless solid
Melting point	120 °C (248 °F; 393 K) source^[1]
Acidity (pK_a)	5.21^[2]
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 salt of pyridine and p-toluenesulfonic acid. It is a colourless solid.

Uses

In organic synthesis, PPTS is used as a weakly acidic catalyst. For example, PPTS is used to deprotect silyl ethers or tetrahydropyranyl ethers when a substrate is unstable to stronger acid catalysts.

References

↑ TOKYO CHEMICAL INDUSTRY CO., LTD. "Pyridinium p-Toluenesulfonate". Retrieved 2011-09-16.
↑ David A. Evans (2005-11-04). "Evans pKa Table" (PDF). Retrieved 2016-03-02.

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