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402885

Sigma-Aldrich

p-Toluenesulfonic acid monohydrate

ACS reagent, ≥98.5%

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
Beilstein/REAXYS Number:
3568023
EC Number:
203-180-0
MDL number:
MFCD00142137
UNSPSC Code:
12352100
PubChem Substance ID:
24865132
NACRES:
NA.21

grade

ACS reagent

Quality Level

200

vapor density

5.9 (vs air)

assay

≥98.5%

form

solid

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%

SMILES string

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

InChI

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

InChI key

KJIFKLIQANRMOU-UHFFFAOYSA-N

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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.

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.

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

Aquatic Chronic 3 - Eye Dam. 1 - Met. Corr. 1 - Skin Corr. 1C - STOT SE 3

target_organs

Respiratory system

Storage Class

8A - Combustible, corrosive hazardous materials

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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Sigma-Aldrich

152536

Sodium p-toluenesulfonate

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)
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)
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)
Solubilities of p-Toluenesulfonic Acid Monohydrate and Sodium p-Toluenesulfonate in Aqueous Sulfuric Acid Solutions and Its Application for Preparing Sodium p-Toluenesulfonate.
Zhao W, et al.
Industrial & Engineering Chemistry Research, 52(51), 18466-18471 (2013)
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)
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