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Sigma-Aldrich

Pyridinium p-toluenesulfonate

puriss., ≥99.0% (T)

Synonym(s):

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

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About This Item

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

grade

puriss.

Quality Level

Assay

≥99.0% (T)

form

crystals

mp

117-120 °C

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. This method has been adapted in the completely symmetric synthesis of tetrahydrolipstatin. It is also capable of selectively cleaving tert-butyldimethylsilyl (TBDMS) ethers in the presence of tert-butyldiphenlysilyl (TBDPS) ethers.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

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)
L.A. Paquette et al.
Journal of the American Chemical Society, 103, 6526-6526 (1981)
G.E. Keck et al.
Tetrahedron Letters, 22, 2615-2615 (1981)

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