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p-Toluenesulfonic acid
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Name

p-Toluenesulfonic acid

 EINECS 203-180-0
CAS No. 104-15-4 Density 1.34 g/cm3
PSA 62.75000 LogP 2.32250
Solubility soluble Melting Point 106~107 °C
Formula C7H8O3S Boiling Point 116 °C
Molecular Weight 172.205 Flash Point 41 °C
Transport Information UN 2585 Appearance clear colorless to light yellow solution
Safety 45-26-23 Risk Codes 34-10
Molecular Structure Molecular Structure of 104-15-4 (p-Toluenesulfonic acid) Hazard Symbols CorrosiveC
Synonyms

P-Toluene sulfonic acid monohydrate;2-Toluene Sulfonic Acid;4-Toluene sulfonic acid;P-Toluosulfonic Acid Monohydrate;Methylbenzenesulfonic acid;Toluene-p-sulfonate;4-methylbenzenesulfonic acid;Cyzac 4040;4-Toluenesulfonic acid;Cyclophil P T S A;Benzenesulfonic acid, methyl-;p-toluene sulfonic acid;Toluene-4-sulfonic acid;ar-Toluenesulfonic acid;Kyselina p-toluenesulfonova;p-Toluene-sulfonic acid;Toluene-4-sulfonate;Benzenesulfonic acid, 4-methyl-;Benzenesulfonic acid,4-methyl-;Eltesol;p-Tolylsulfonic acid;p-Methylbenzene sulfonic acid;toluene-4-sulphonic acid;o-toluenesulfonic Acid;

Article Data 298

p-Toluenesulfonic acid Synthetic route

98-59-9

p-toluenesulfonyl chloride

104-15-4

toluene-4-sulfonic acid

Conditions
ConditionsYield
With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; water; phenylzinc(II) bromide In tetrahydrofuran at 0 - 20℃; Inert atmosphere;100%
Stage #1: p-toluenesulfonyl chloride With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 22℃;
Stage #2: With trifluoroacetic acid In dichloromethane Further stages.;		95%
With pyridine; dmap In dichloromethane82%
106-45-6

para-thiocresol

104-15-4

toluene-4-sulfonic acid

Conditions
ConditionsYield
With dinitrogen tetraoxide In tetrachloromethane; diethyl ether for 2.5h; Ambient temperature;100%
With dihydrogen peroxide; trichlorophosphate In water at 80℃; for 1.16667h; Micellar solution;95%
With HOF* CH3CN In dichloromethane at 0℃;90%
With dihydrogen peroxide; methyltrioxorhenium(VII) In acetonitrile at 20℃;87%
Multi-step reaction with 2 steps
1: pyridine / acetonitrile / Heating
2: hydrogenchloride; water / 40 °C
View Scheme
26177-05-9

1-(p-methylbenzenesulfonoyloxy)-2(1H)-quinolone

A

104-15-4

toluene-4-sulfonic acid

B

58-57-1

1-hydroxycarbostyril

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran for 2h; Product distribution; Ambient temperature;A n/a
B 98%
15404-00-9

triethylammonium toluene-p-sulfonate

104-15-4

toluene-4-sulfonic acid

Conditions
ConditionsYield
With sulfuric acid In water pH=3;97.5%

(1,1-dioxido-4-oxo-3-phenyl-4H-thiochromen-2-yl)methyl 4-methylbenzenesulfonate

A

1033736-87-6

C16H10O3S

B

104-15-4

toluene-4-sulfonic acid

Conditions
ConditionsYield
In chloroform-d1 for 0.233333h; Photolysis; Inert atmosphere;A n/a
B 97%
103-19-5

di(p-tolyl) disulfide

104-15-4

toluene-4-sulfonic acid

Conditions
ConditionsYield
With dihydrogen peroxide; trichlorophosphate In water at 80℃; for 1h; Micellar solution;94%
108-88-3

toluene

104-15-4

toluene-4-sulfonic acid

Conditions
ConditionsYield
With sulfur trioxide at 35 - 65℃; Temperature; Inert atmosphere;93.3%
With sodium hydrogensulfite; pyridinium chlorochromate In neat (no solvent) at 100℃; under 1500.15 Torr; for 0.0666667h; Reagent/catalyst; Microwave irradiation;93%
With 1,3-disulfonic acid imidazolonium chloride In water at 50℃; for 0.05h; Green chemistry; regioselective reaction;72%
84877-44-1

toluene-4-sulfonic acid 2,2,2-trifluoro-1-p-tolyl-ethyl ester

104-15-4

toluene-4-sulfonic acid

Conditions
ConditionsYield
With trifluoroacetic acid In water at 20℃; for 2h;91%
64-04-0

phenethylamine

98-59-9

p-toluenesulfonyl chloride

A

5450-75-9

4-methyl-N-(2-phenylethyl)benzenesulfonamide

B

104-15-4

toluene-4-sulfonic acid

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at -50℃; for 2h; Product distribution; Mechanism; further amines;A 90%
B 10%
With n-butyllithium 1) THF, hexane, -10 deg C, 15 min, 2) THF, hexane, -50 deg C, 2 h; Yield given. Multistep reaction. Yields of byproduct given;
478363-68-7

phenylmethyl 3,5,6,7,8,8a-hexahydro-5,5,8a-trimethyl-6-(trifluoroacetylamino)-(6β,8aβ)-2(1H)-isoquinolinecarboxylate

A

N-Trifluoroacetyl-1,2,3,5,6,7,8,8a-octahydro-5,5,8a-trimethyl-(6β,8aβ)-6-isoquinolineamine 4-methylbenzenesulfonate

B

104-15-4

toluene-4-sulfonic acid

Conditions
ConditionsYield
In ethanol; di-isopropyl ether; palladiumA n/a
B 90%

p-Toluenesulfonic acid Chemical Properties

The Molecular Structure of p-Toluenesulfonic acid (CAS NO.104-15-4):

Empirical Formula: C7H8O3S
Molecular Weight: 172.2016 
IUPAC Name: 4-methylbenzenesulfonic acid  
Appearance: Clear colorless to light yellow solution
Product Categories: FINE Chemical & INTERMEDIATES;Organics
Nominal Mass: 172 Da
Average Mass: 172.2016 Da
Monoisotopic Mass: 172.019414 Da 
Index of Refraction: 1.562
Molar Refractivity: 41.72 cm3
Molar Volume: 128.4 cm3
Surface Tension: 48.2 dyne/cm
Density: 1.34 g/cm3 
Boiling point: 116 ºC
Refractive index: 1.3825-1.3845
Flash point: 41 ºC
Storage temp: Flammables area
Water Solubility: soluble
InChI
InChI=1/C7H8O3S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3,(H,8,9,10)
Smiles
S(c1ccc(C)cc1)(O)(=O)=O 
It is abbreviated as TsOH,it is white solid , soluble in water, alcohols, and other polar organic solvents. Most often, TsOH refers to the monohydrate, TsOH.H2O. 

p-Toluenesulfonic acid Uses

 p-Toluenesulfonic acid (CAS NO.104-15-4) is used for pharmaceutical, pesticide, dyestuff, also used in plastics and detergent and printing coatings.

p-Toluenesulfonic acid Production

 p-Toluenesulfonic acid (CAS NO.104-15-4) is prepared on an industrial scale by the sulfonation of toluene. Common impurities include benzenesulfonic acid and sulfuric acid. Impurities can be removed by recrystallization from concentrated hydrochloric acid followed by azeotropic drying.

p-Toluenesulfonic acid Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
quail LD50 oral > 316mg/kg (316mg/kg)   Ecotoxicology and Environmental Safety. Vol. 6, Pg. 149, 1982.
rat LD50 oral 2480mg/kg (2480mg/kg)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 1055, 1986

p-Toluenesulfonic acid Safety Profile

Hazard Codes: CorrosiveC
Risk Statements: 34-10 
R34: Causes burns
R10: Flammable
Safety Statements: 45-26-23 
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S23: Do not breathe vapour
RIDADR: 2585
HazardClass: 8
PackingGroup: III

p-Toluenesulfonic acid Specification

 p-Toluenesulfonic acid (CAS NO.104-15-4) is also called as 4-Methylbenzenesulfonic acid ; 4-Toluenesulfonic acid ; Benzenesulfonic acid, 4-methyl- ; Toluene sulfonic acid ; 4-Methylbenzenesulfonic acid ; 4-Toluenesulfonic acid ; Benzenesulfonic acid, 4-methyl- ; Eltesol ; Kyselina p-toluenesulfonova ; Methylbenzenesulfonic acid ; Toluenesulfonic acid ; Toluenesulfonic acid (VAN) ; p-Toluene sulfonate ; p-Toluenesulphonic acid ; p-Toluolenesulfonic acid ; Toluene-4-sulphonic acid ; Benzenesulfonic acid, 4-methyl- ; Toluenesulfonic acid ; p-Toluenesulfonic acid .

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