402885

Sigma-Aldrich

p-Toluenesulfonic acid monohydrate

ACS reagent, ≥98.5%

Linear Formula:
CH3C6H4SO3H · H2O
CAS Number:
Molecular Weight:
190.22
Beilstein/REAXYS Number:
3568023
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.21

Quality Level

grade

ACS reagent

vapor density

5.9 (vs air)

assay

≥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%

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.

Packaging

5 g in glass bottle
100, 500 g in poly bottle

pictograms

Corrosion

signalword

Danger

hazcat

Aquatic Chronic 3 - Eye Dam. 1 - Met. Corr. 1 - Skin Corr. 1B

storage_class_code

8A - Combustible, corrosive hazardous materials

WGK Germany

WGK 1

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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)
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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