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Merck

82815

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:
24057-28-1
Molecular Weight:
251.30
UNSPSC Code:
12352106
NACRES:
NA.22
PubChem Substance ID:
329769266
EC Number:
246-002-7
Beilstein/REAXYS Number:
3764305
MDL number:
MFCD00013108

Product Name

Pyridinium p-toluenesulfonate, puriss., ≥99.0% (T)

InChI key

ZDYVRSLAEXCVBX-UHFFFAOYSA-N

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

SMILES string

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

grade

puriss.

assay

≥99.0% (T)

form

crystals

mp

117-120 °C

functional group

tosylate

Quality Level

200

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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

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN8731
BCCN3097
BCCN1057
BCCL8321
BCCM3116

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