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82815

Sigma-Aldrich

Pyridinium p-toluenesulfonate

puriss., ≥99.0% (T)

Synonym(s):

p-Toluenesulfonic acid pyridine salt, PPTS, Pyridine p-toluenesulfonate

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25 G
$78.20
100 G
$162.00

About This Item

Empirical Formula (Hill Notation):
C12H13NO3S
CAS Number:
Molecular Weight:
251.30
Beilstein/REAXYS Number:
3764305
EC Number:
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.22

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grade

puriss.

Quality Level

assay

≥99.0% (T)

form

crystals

mp

117-120 °C

functional group

tosylate

SMILES string

c1ccncc1.Cc2ccc(cc2)S(O)(=O)=O

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 key

ZDYVRSLAEXCVBX-UHFFFAOYSA-N

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Application

Pyridinium p-toluenesulfonate is a mild and efficient catalyst for the formation and cleavage of acetals.[1][2][3][4][5][6][7] This method has been adapted in the completely symmetric synthesis of tetrahydrolipstatin.[8] It is also capable of selectively cleaving tert-butyldimethylsilyl (TBDMS) ethers in the presence of tert-butyldiphenlysilyl (TBDPS) ethers.[9]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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R.S. Bhide et al.
Tetrahedron Letters, 27, 671-671 (1986)
Pyridinium p-toluenesulfonate. A mild and efficient catalyst for the tetrahydropyranylation of alcohols
N. Miyashita et al.
The Journal of Organic Chemistry, 42, 3773-3773 (1977)
L.A. Paquette et al.
The Journal of Organic Chemistry, 46, 3368-3368 (1981)
H. Monti et al.
Synthetic Communications, 13, 1021-1021 (1983)
R. Sterzycki
Synthesis, 724-724 (1979)

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