p-TOLUENESULFONIC ACID

CAS Number: 6192-52-5
Molecular Weight: 190.22
EC Number: 203-180-0

PubChem Substance ID: 87576246
Molecular Formula: C7H10O4S

APPLICATIONS

p-Toluenesulfonic acid is used as initiator for catalytic polymerization of caprolactam, catalyst for dimerization of alpha- methylstyrene.

p-Toluenesulfonic acid is used in manufacture of dyes and oral antidiabetic drugs; conversion to sodium and ammonium salts for manufacture of hydrotropes.
Further, p-Toluenesulfonic acid is a catalyst in coatings, paint, polymer, and textile industries.

p-Toluenesulfonic acid is a stabilizer for monomers and polymers, pharmaceutical intermediate, cleaning agents, plating additive.

p-Toluenesulfonic acid (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.

p-Toluenesulfonic acid is used in the chemical industry as a catalyst.
Also, p-Toluenesulfonic acid is used in the manufacturing of textile dyes, drugs, cleaning agents, polymers, and paints.

p-Toluenesulfonic acid is used in photography (color bleaching).
More to that ,p-Toluenesulfonic acid is used as a catalyst (with applications including resins in foundry cores), as a curing agent for resins, as a descaling agent (industrial metal cleaners), in electroplating bathes, plastics, dyes, pharmaceutical intermediates, food packaging adhesives, and as a coupling and wetting agent.

p-Toluenesulfonic acid 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.

p-Toluenesulfonic acid (Lisinopril EP Impurity B) is used in the synthesis of resveratrol.
Also, p-Toluenesulfonic acid is used in the synthesis of oxane derivatives as antimalarial agents.

p-Toluenesulfonic acid is used as a catalyst in the synthesis of resveratrol, in oxane derivatives as an antimalarial agent, as substituted piperidine and unsymmetrical benzyl.

p-Toluenesulfonic acid acts as a catalyst in the preparation of 1,3,5-trisubstituted pyrazoles derivatives, selenated ketene dithioacetals, triazoloquinazolinone and benzimidazoquinazolinone derivatives.

p-Toluenesulfonic acid also serves as an intermediate in the esterification and in reductive amination reactions.
Also, p-Toluenesulfonic acid is prepared on an industrial scale by the sulfonation of toluene.
Common impurities include benzenesulfonic acid and sulfuric acid.

p-Toluenesulfonic acid contains an amount of water.
To estimate the total moisture present as impurity, the Karl Fischer method is used.
Impurities can be removed by recrystallization from its concentrated aqueous solution followed by azeotropic drying with toluene.

DESCRIPTION

p-Toluenesulfonic acid, an oxonium salt, is an inexpensive and easy to handle organic catalyst used in organic synthesis.
The study of crystalline of p-Toluenesulfonic acid structure shows that it is monoclinic with P21/c space group.

The solubility of p-Toluenesulfonic acid in aqueous sulfuric acid solutions has been studied.

p-Toluenesulfonic acid (4-Methylbenzenesulfonic acid, Tosylic acid, tosic acid, para-toluene) is an extremely strong acidic compound.
The anhydrous acid exists as monoclinic leaflets or prisms, mp 106–107 °C; pKa −6.62 (H2SO4).1
There is also a metastable form of p-Toluenesulfonic acid, mp 38 °C.

p-Toluenesulfonic acid is a white crystalline powder, mp 103–106 °C.

Forms of p-Toluenesulfonic acid:

widely available as the monohydrate, which is commonly used.
Various metal salts are also commercially available.

p-Toluenesulfonic acid is an organic compound with the formula CH3C6H4SO3H.

p-Toluenesulfonic acid, as it is abbreviated, is a white solid that is soluble in water, alcohols, and other polar organic solvents.
Most often, p-Toluenesulfonic acid refers to the monohydrate, TsOH.H2O.

p-Toluenesulfonic acid is is a strong organic acid.
Thus, p-Toluenesulfonic acid is non-oxidizing chemical compound.

p-Toluenesulfonic acid finds use in organic synthesis as an "organic-soluble" acid catalyst.

p-Toluenesulfonic acid is an organic compound with the formula CH3C6H4SO3H.
Beside that, p-Toluenesulfonic acid is an aromatic sulfonic acid, often used as a strong acid catalyst.

p-Toluenesulfonic acid has been used as a reducing agent for the reductive amination of ketones and aldehydes.
Moreover, p-Toluenesulfonic acid is a strong organic acid, about a million times stronger than benzoic acid. 
p-Toluenesulfonic acid is one of the few strong acids that is solid and, hence, conveniently weighed.
Also, unlike some of the strong mineral acids (especially nitric acid, sulfuric acid, and perchloric acid), p-Toluenesulfonic acid is non-oxidizing.

In the presence of p-Toluenesulfonic acid novel deazaflavin-cholestane hybrid compounds have been synthesized in a condensation reaction.
p-Toluenesulfonic acid has also been synthesized in the presence of p-Toluenesulfonic acid monohydrate.

p-Toluenesulfonic acid esters, are a common class of reagents used in the pharmaceutical industry as alkylating agents, catalysts, and in purification steps of the chemical synthesis of a drug substance.

p-Toluenesulfonic acid monohydrate, an oxonium salt, is an inexpensive and easy to handle organic catalyst used in organic synthesis.
More to this, p-Toluenesulfonic acid or tosylic acid (TsOH) is an organic compound with the formula CH3C6H4SO3H.

p-Toluenesulfonic acid is a white extremely hygroscopic solid that is soluble in water, alcohols, and other polar organic solvents.
The CH3C6H4SO2 group is known as the tosyl group and is often abbreviated as Ts or Tos.

Most often, p-Toluenesulfonic acid refers to the monohydrate, TsOH.H2O.[6]

p-Toluenesulfonic acid is used as an acid catalyst soluble in organic solvents, e.g. in esterification reactions and also for the elimination of the hydroxyl group.

Physical description of p-Toluenesulfonic acid:

White, almost white or pale pink crystals

PROPERTIES

grade: ACS reagent
vapor density: 5.9 (vs air)
assay: ≥98.5%
form: solid
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%
Sulfuric acid ≤ 0.3%
Total acid ≥ 97.0% (C7H8O3S · H2O)
Boiling point: 140 ° C (27 hPa)
Flash point: 180 ° C
Flash point: 600 ° C
Melting point: 56 ° C Elimination of water of crystallisation
PH value: 1 (650 g / l, H₂O, 20 ° C) (anhydrous substance)
Bulk density: 510 kg / m3
Solubility: 750 g / l

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

Appearance: White to Almost white powder to crystal
Purity(HPLC): min. 98.0 area%
Purity(Neutralization titration): 98.0 to 102.0 %(after drying)
Melting point: 104.0 to 107.0 °C
Solubility in Water: almost transparency
Drying loss: max. 3.0 %
Melting Point: 106 °C
Boiling Point: 140 °C/20 mmHg
Solubility in water: Soluble
Degree of solubility in water: 670 g/l  
Solubility (soluble in): Ether,Alcohol

FIRST AID

Eyes:

Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids.
Get medical aid imme diately.

Skin:

Get medical aid immediately.
Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.

Ingestion:

Do not induce vomiting.
Get medical aid immediately.
Call a poison control center.

Inhalation:

Get medical aid immediately.
Remove from exposure and move to fresh air immediately.
If breathing is difficult, give oxygen.
Do not use mouth-to-mouth resuscitation if victim ingested or inhaled the substance; induce artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device.

Notes to Physician:

Treat symptomatically and supportively.

HADNLING AND STORAGE

p-Toluenesulfonic acid is highly toxic, oxidizing agent.
p-Toluenesulfonic acid is extremely irritating to the skin and mucous membranes.

Use of gloves and protective clothing is recommended.

Use p-Toluenesulfonic acid in a fume hood.

SYNONYMS

203-180-0 [EINECS]
4-methylbenzenesulfonic acid hydrate
4-Methylbenzenesulfonic acid hydrate (1:1) [ACD/IUPAC Name]
4-Methylbenzenesulfonic acid monohydrate
4-Methylbenzolsulfonsäurehydrat (1:1) [German] [ACD/IUPAC Name]
6192-52-5 [RN]
Acide 4-méthylbenzènesulfonique, hydrate (1:1) [French] [ACD/IUPAC Name]
Benzenesulfonic acid, 4-methyl-, hydrate (1:1) [ACD/Index Name]
benzenesulfonic acid, 4-methyl-, monohydrate
MFCD00142137 [MDL number]
p-Toluene sulfonic acid monohydrate
p-Toluenesulfonic acid monohydrate
toluene-p-sulfonic acid monohydrate
1-Hydrate
4-methylbenzene-1-sulfonic acid hydrate
4-methylbenzenesulfonic acid;hydrate
4-Methylbenzenesulphonic Acid Hydrate
4-Methylbenzene-sulphonic Acid Hydrate
4-toluene sulfonic acid monohydrate
4-Toluenesulfonic acid monohydrate
612-715-0 [EINECS]
hydrate
missing
OXIDANIUM 4-METHYLBENZENE-1-SULFONATE
OXIDANIUM TOSYLATE
p
p-​toluenesulfonic acid monohydrate
PARA-TOLUENE SULFONATE HYDRATE
PARA-TOLUENE SULFONIC ACID HYDRATE
para-toluene sulfonic acid monohydrate
para-Toluenesulfonic acid monohydrate
p-Toluene Sulfinic Acid
p-toluene sulfonic acid hydrate
p-toluene sulphonic acid monohydrate
p-toluenesulfonic acid hydrate
p-Toluenesulfonic Acid, Monohydrate
p-Toluenesulfonic acid, Tosylic acid, Tosic acid, PTSA
p-toluenesulfonicacidmonohydrate
p-Toluenesulphonic acid monohydrate
p-toluensulfonic acid monohydrate
tert-butyl 4-pyrrolidin-1-ylpiperidine-1-carboxylate
Toluene sulfonic acid hydrate
Toluene-4-sulfonic acid monohydrate
toluenesulfonic acid hydrate
-toluenesulfonic acid monohydrate
TSA-MH [Trade name]
对甲苯磺酸
p-Toluenesulfonic acid monohydrate
6192-52-5
4-methylbenzenesulfonic acid hydrate
4-Methylbenzenesulfonic acid monohydrate
p-Toluenesulphonic acid monohydrate
p-Toluene sulfonic acid monohydrate
Benzenesulfonic acid, 4-methyl-, monohydrate
UNII-3BTO78GAFF
4-toluenesulfonic acid monohydrate
4-methylbenzenesulfonic acid;hydrate
para-toluenesulfonic acid monohydrate
MFCD00142137
3BTO78GAFF
4-methylbenzene-1-sulfonic acid hydrate
4-methylbenzenesulphonic acid hydrate
p-Toluenesulfonic acid (monohydrate)
para-toluene sulfonic acid monohydrate
TsOH
p-TSA
ptoluenesulfonic acid
C7H8O3S.H2O
tosylate hydrate
TsOH hydrate
para-toluenesulfonic acid hydrate
TsOH.water
p-Toluenesulfonic acid, monohydrate
tosylate monohydrate
tosylic acid hydrate
ptoluene sulfonic acid
pTSA HOH
pTsOH H2O
pTsOH.H2O
TosOH.H2O
p-TsOH H2O
p-TsOH.H2O
pTSA H2O
Tos-OH.H2O
tosylic acid monohydrate
TsOH H2O
TsOH-H2O
TsOH.H2O
PTSA.H2O
p-TSA H2O
Ts-OH.H2O
p-toluene sulfonate hydrate
p-toluenesulfonic acid H2O
p-toluenesulfonic acid.H2O
SCHEMBL5350
DSSTox_CID_24316
DSSTox_RID_80149
DSSTox_GSID_44316
p-toluene sulfonic acid.H2O
p-toluenesufonic acid hydrate
p-toluensulfonic acid hydrate
p-toluenesulfonate monohydrate
4-toluenesulfonate monohydrate
p-toluenesulfonic acid hydrate
p-toluenesulfonic acid-hydrate
104-15-4 (anhydrous)
4-toluenesulfonic acid hydrate
p-toluene sulfonate monohydrate
p-toluenesulphonic acid hydrate
p-toluenesulphonic acid-hydrate
4-toluenesulphonic acid hydrate
p-Toluene sulfonic acid hydrate
p-toluene sulfonic acid-hydrate
p-toluene-sulfonic acid hydrate
p-toluenesulfonic acid. hydrate
toluene-p-sulfonic acid hydrate
p-toluenesulfonic acidmonohydrate
toluene-4-sulfonic acid hydrate
4toluenesulfonic acid monohydrate
CHEMBL3183883
DTXSID5044316
p-toluene sulphonic acid hydrate
p-toluenesufonic acid monohydrate
p-Toluenesulfonicacid monohydrate
p-toluensulfonic acid monohydrate
para-toluenesulfonic acid-hydrate
paratoluene sulfonic acid hydrate
toluene-p-sulphonic acid hydrate
4-methylbenzenesulfonicacidhydrate
4-toluene-sulphonic acid hydrate
toluene-4-sulphonic acid hydrate
p-toluene sulfonic acidmonohydrate
p-toluenesulfonic acid-monohydrate
p-toluensulphonic acid monohydrate
para toluene-sulfonic acid hydrate
para-toluene sulfonic acid hydrate
p-toluenesulphonic acid-monohydrate
4-toluenesulphonic acid monohydrate
p- toluenesulfonic acid monohydrate
p-toluene sulfonic acid monohydrate
p-toluene sulfonic acid-monohydrate
p-toluene-sulfonic acid monohydrate
p-toluenes ulfonic acid monohydrate
p-toluenesulfonic acid mono hydrate
p-toluenesulfonic acid mono-hydrate
p-toluenesulfonic acid. monohydrate
toluene-p-sulfonic acid monohydrate
4-toluene sulfonic acid monohydrate
4-toluene-sulfonic acid monohydrate
BCP25868
p-toluene sulphonic acid monohydrate
p-toluene-sulphonic acid monohydrate
p-toluenesulphonic acid, monohydrate
para-toluensulfonic acid monohydrate
paratoluenesulphonic acid monohydrate
rho-toluenesulfonic acid monohydrate
toluene 4-sulfonic acid monohydrate
toluene-4 sulfonic acid monohydrate
toluene-4-sulfonic acid monohydrate
toluene-p-sulphonic acid monohydrate
4-toluenesulphonic acid mono hydrate
p-toluene sulfonic acid mono hydrate
p-toluene sulfonic acid-mono hydrate
para-toluenesulfonic acid-monohydrate
paratoluene sulfonic acid monohydrate
paratoluene-sulfonic acid monohydrate
toluene-4-sulphonic acid monohydrate
Tox21_300710
4-methyl benzenesulfonic acid hydrate
4-methylbenzenesulfonic acid, hydrate
AC-793
s6188
para-toluenesulfonic acid mono hydrate
para-toluenesulfonic acid mono-hydrate
para-toluenesulfonic acid, monohydrate
para-toluenesulphonic acid monohydrate
AKOS000121975
p-Toluenesulfonic acid monohydrate, CP
para toluene sulphonic acid monohydrate
para-toluene sulphonic acid monohydrate
CS-W015891
HY-W015175
para-toluene sulfonic acid mono hydrate
SB18320
4-methylbenzenesulfonic acid-monohydrate
para-toluene sulphonic acid mono hydrate
4-Methyl benzenesulfonic acid monohydrate
4-methylbenzenesulfonic acid mono hydrate
4-methylbenzenesulphonic acid monohydrate
NCGC00254617-01
(4-methylphenyl)sulfonic acid monohydrate
BP-11003
CAS-6192-52-5
FT-0619528
p-Toluenesulfonic acid monohydrate, ACS grade
D77781
p-Toluenesulfonic acid monohydrate, AR, >=99%
A833488
p-Toluenesulfonic acid monohydrate, p.a., 98.5%
Q27257015
p-Toluenesulfonic acid monohydrate, reagent grade, 98%
p-Toluenesulfonic acid monohydrate, ACS reagent, >=98.5%
p-Toluenesulfonic acid monohydrate, ReagentPlus(R), >=98%
p-Toluenesulfonic acid monohydrate, SAJ first grade, >=99.0%
p-Toluenesulfonic acid monohydrate, SAJ special grade, >=99.0%
p-Toluenesulfonic acid monohydrate, Vetec(TM) reagent grade, 98%
p-Toluenesulfonic acid monohydrate, >=98.0% (T), >=98.0% (HPLC)
p-Toluenesulfonic acid monohydrate, >=99% (calc. to H2O free subst.)
p-Toluenesulfonic acid monohydrate, puriss., for acetyl determination, >=98.5% (T)
METHYLBENZENESULFONIC ACID MONOHYDRATE 4-METHYLBENZENESULFONIC ACID MONOHYDRATE 4-TOLUENESULFONIC ACID MONOHYDRATE 4-TOLUENESULPHON
4-Methylbenzenesulfonic acid monohydrate, Tosylic acid monohydrate, tosic acid monohydrate, para-toluene sulfonate monohydrate, tosylate monohydrate