Pyridinium p-toluenesulfonate

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Pyridinium p-toluenesulfonate

IUPAC name 4-methylbenzenesulfonate; pyridin-1-ium
Other names pyridinium p-toluenesulfonate
Identifiers
Abbreviations	PPTS
CAS number	24057-28-1^Y
PubChem	466102
ChemSpider	141806^Y
Jmol-3D images	{{#if:Cc1ccc(cc1)S(=O)(=O)[O-].c1cc[nH+]cc1\|Image 1
SMILES Cc1ccc(cc1)S(=O)(=O)[O-].c1cc[nH+]cc1
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
Properties
Molecular 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]
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Pyridinium p-toluenesulfonate is a salt of pyridine and p-toluenesulfonic acid. It is often called PPTS. It appears as a colourless solid.

Masaki Miyashita studied this compound and found it efficient in deprotection of tetrahydropyranyl groups (THP).^[3]

Uses

In organic synthesis, p-toluenesulfonate 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 2011-09-16.
↑ Miyashita, M.; Yoshikoshi, A.; Grieco, P. A. (1977). "Pyridinium p-toluenesulfonate. A mild and efficient catalyst for the tetrahydropyranylation of alcohols". J. Org. Chem. 42 (23): 3772–3774. doi:10.1021/jo00443a038.

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