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Merck
CN

402885

p-Toluenesulfonic acid monohydrate

ACS reagent grade, ≥98.5%, solid

Synonym(s):

4-Methylbenzenesulfonic acid monohydrate, 4-Toluenesulfonic acid monohydrate, PTSA monohydrate, TsOH monohydrate

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About This Item

Linear Formula:
CH3C6H4SO3H · H2O
CAS Number:
6192-52-5
Molecular Weight:
190.22
NACRES:
NA.21
PubChem Substance ID:
24865132
UNSPSC Code:
12352100
EC Number:
203-180-0
MDL number:
MFCD00142137
Beilstein/REAXYS Number:
3568023

Key Documents

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Product Name

p-Toluenesulfonic acid monohydrate, ACS reagent, ≥98.5%

InChI key

KJIFKLIQANRMOU-UHFFFAOYSA-N

InChI

1S/C7H8O3S.H2O/c1-6-2-4-7(5-3-6)11(8,9)10;/h2-5H,1H3,(H,8,9,10);1H2

SMILES string

[H]O[H].Cc1ccc(cc1)S(O)(=O)=O

grade

ACS reagent

vapor density

5.9 (vs air)

assay

≥98.5%

form

solid

concentration

≥98.5%

clarity of soln

passes test

impurities

9.5-11.5% water

ign. residue

≤0.1%

mp

103-106 °C (lit.)

solubility

H2O: 10g + 50 mL, clear, colorless

anion traces

sulfate (SO42-): ≤0.3%

cation traces

Fe: ≤0.01%
Na: ≤0.002%
heavy metals (as Pb): ≤0.001%

functional group

tosylate

Quality Level

300

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Application

p-Toluenesulfonic acid monohydrate (p-TsOH·H2O) may be used as a catalyst in the synthesis of the following:
  • Unsymmetrical benzils.
  • Highly substituted piperidines.
  • 1,3,5-Trisubstituted benzenes by trimerization of alkynes.
  • Triazoloquinazolinone and benzimidazoquinazolinone derivatives.
  • 1,3,5-Trisubstituted pyrazoles derivatives.
  • Selenated ketene dithioacetals.

General description

p-Toluenesulfonic acid monohydrate, an oxonium salt, is an inexpensive and easy to handle organic catalyst used in organic synthesis. The study of its crystalline structure shows that it is monoclinic with P21/c space group. Its solubility in aqueous sulfuric acid solutions has been studied.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ8226
0000509210
0000509210
0000506752
MKCZ6516

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One-pot multicomponent synthesis of highly substituted piperidines using p-toluenesulfonic acid monohydrate as catalyst.
Sajadikhah SS, et al.
Monatshefte fur Chemie / Chemical Monthly, 143(6), 939-945 (2012)
Catalytic systems containing p-toluenesulfonic acid monohydrate catalyzed the synthesis of triazoloquinazolinone and benzimidazoquinazolinone derivatives.
Mousavi MR and Maghsoodlou MT.
Monatshefte fur Chemie / Chemical Monthly, 145(12), 1967-1973 (2014)
An efficient approach to the cyclotrimerisation of alkynes: solvent-free synthesis of 1, 3, 5-trisubstituted benzenes using p-toluenesulfonic acid monohydrate.
Gao Q, et al.
ARKIVOC (Gainesville, FL, United States), 3, 49-60 (2013)
Br?nsted acid-catalyzed phenylselenenylation of internal olefins.
Wu P, et al.
Tetrahedron Letters, 56(19), 2488-2491 (2015)
One-pot synthesis of unsymmetrical benzils from aryl methyl ketones and arenes in the presence of selenous acid catalysed by p-toluenesulfonic acid monohydrate.
Kharkongor I, et al.
Tetrahedron Letters, 53(23), 2837-2841 (2012)
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