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p-Toluenesulfonic acid (PTSA) or tosylic acid (TsOH) is an organic compound with the formula CH3C6H4SO3H.
p-Toluenesulfonic acid (PTSA) 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.
CAS: 104-15-4
MF: C7H8O3S
MW: 172.2
EINECS: 203-180-0
Synonyms
TL65;TL65LS;PARATOLUENE SULPHONIC ACID;p-tolylsulfonicacid;PTSA 70;toluene-4-sulphonic;Toluene-p-sulfonate;toluenesulfonicacid,liquid,withmorethan5%freesulfuricacid;P-TOLUENESULFONIC ACID;4-Methylbenzenesulfonic acid;104-15-4;4-Toluenesulfonic acid;p-Toluenesulphonic acid;Toluene-4-sulfonic acid;Tosic acid;p-Tolylsulfonic acid;Tosylic acid;Toluenesulfonic acid;Benzenesulfonic acid, 4-methyl-;p-Methylbenzenesulfonic acid;p-Methylphenylsulfonic acid;Eltesol;p-Toluenesulfonate;Toluene sulfonic acid;Methylbenzenesulfonic acid;Cyclophil P T S A;PARA-TOLUENE SULFONATE;ar-Toluenesulfonic acid;p-Toluolenesulfonic acid;PTSA;Toluene-4-sulphonic acid;P-Toluene Sulfonic acid;Cyzac 4040;Kyselina p-toluenesulfonova;Nacure 1040;Manro PTSA 65 E;Manro PTSA 65 H;TSA-HP;TSA-MH;Benzenesulfonic acid, methyl-;Manro PTSA 65 LS;p-Toluene sulfonate;Kyselina p-toluensulfonova;K-Cure 1040;Toluen-4-sulfonsaeure;K-Cure 040;HSDB 2026;Toluene-p-sulfonate;NSC 167068;p-toluene sulphonic acid;para-toluenesulfonic acid;Eltesol TSX;EINECS 203-180-0;UNII-QGV5ZG5741;BRN 0472690;p-toluensulfonic acid;QGV5ZG5741;DTXSID0026701;CHEBI:27849;AI3-26478;p-Toluene-sulfonic acid;NSC-2167;para-toluenesulphonic acid;ACTIVATOR-100T3;TAYCATOX-300;NSC-167068;DRYER-900;NACURE-1040;4-Toluene sulfonic acid;CHEMBL541253;CYZAC-4040;DTXCID406701;TSA-95;4-TOLUENE-SULFONIC ACID;EC 203-180-0;4-11-00-00241 (Beilstein Handbook Reference);AD-3302W;KC-1040;TsOH;WLN: WSQR D1;p-TSA;Toluenesulfonic acid (VAN);TSU;LISINOPRIL IMPURITY B (EP IMPURITY);LISINOPRIL IMPURITY B [EP IMPURITY];2(Or 4)-toluenesulphonic acid;ANASTROZOLE IMPURITY F (EP IMPURITY);ANASTROZOLE IMPURITY F [EP IMPURITY];P-TOLUENESULFONIC ACID (EP IMPURITY);P-TOLUENESULFONIC ACID [EP IMPURITY];SULTAMICILLIN IMPURITY B (EP IMPURITY);toluene-p-sulfonic acid;Kyselina p-toluenesulfonova [Czech];paratoluene sulphonic acid;para toluene sulfonic acid;TIZANIDINE HYDROCHLORIDE IMPURITY I (EP IMPURITY);TIZANIDINE HYDROCHLORIDE IMPURITY I [EP IMPURITY];TosicAcid;4-sulphotoluene;pTsOH;TosOH;p-toluenesulfonicacid;P-Toluene Sulfonic acid(monohydrate);p-TsOH;Tos-OH;p-toluenesufonic acid;4-Toluenesulfonicacid;p-toluene sulfonicacid;p-toluene-sulfonicacid;p-toluensulphonic acid;paratoluensulfonic acid;25231-46-3;Ts-OH;p-toluen sulfonic acid;p-toluenesuiphonic acid;p-toluenylsulfonic acid;paratoluenesulfonic acid;4-toluenesulphonic acid;p -toluenesulfonic acid;p- toluenesulfonic acid;p-tolu-enesulfonic acid;p-toluyl sulphonic acid;toluene p-sulfonic acid;para-toluensulfonic acid;rho-toluenesulfonic acid;paratoluenesulphonic acid;p-toluene-sulphonic acid;toluene 4-sulfonic acid;toluene p-sulphonic acid;toluene-p-sulphonic acid;para toluenesulfonic acid;paratoluene sulfonic acid;paratoluene-sulfonic acid;SCHEMBL34;4-toluene sulphonic acid;4-toluene-sulphonic acid;rho-toluene sulfonic acid;para toluenesulphonic acid;para-toluene sulfonic acid;para-toluene-sulfonic acid;4methylbenzenesulfonic acid;4-methylphenylsulfonic acid;para toluene sulphonic acid;para-toluene sulphonic acid;4-methylphenylsulphonic acid;NCIOpen2_002932;NCIOpen2_003096;4-methylbenzenesulphonic acid;4-methyl-benzenesulfonic acid;4-methylbenzene sulfonic acid;4-methylbenzene-sulfonic acid;p-toluenesulfonic acid (ptsa);4-methyl benzene sulfonic acid;4-methyl-benzene sulphonic acid;4-methyl-benzene-sulphonic acid;4-methylbenzene-1-sulfonic acid;NSC2167;PTS-100;4-Toluenesulfinic acid sodium salt;P-TOLUENESULFONIC ACID [MI];Tox21_202364;AC-794;BDBM50294029;MFCD00064387;NSC167068;STL199173;AKOS008966288;AT27303;CS-W019626;DB03120;NCGC00248146-01;NCGC00248146-02;NCGC00248146-03;NCGC00259913-01;AS-82150
;BP-31081;CAS-104-15-4;SY011236;1ST001660;DB-050363;NS00010519;T0267;C06677;AE-848/00887005;Q285878;SR-01000944854;J-001117;Q-200514;SR-01000944854-1;F1908-0079;InChI=1/C7H8O3S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3,(H,8,9,10
Most often, p-Toluenesulfonic acid (PTSA) refers to the monohydrate, TsOH.H2O.
As with other aryl sulfonic acids, p-Toluenesulfonic acid (PTSA) is a strong organic acid.
p-Toluenesulfonic acid (PTSA) is about one million times stronger than benzoic acid.
p-Toluenesulfonic acid (PTSA) is one of the few strong acids that is solid and therefore is conveniently weighed and stored.
p-Toluenesulfonic acid (PTSA) (Its molecular structural formula is p-CH3C6H4SO3H, also known as TsOH, English name is p-toluene sulfonic acid) referred to as PTS, is a non-oxidizing organic acid, white needle or powder crystals, soluble in water, alcohols, ethers and other polar solvents.
Easy deliquescence, easy to make wood, cotton fabric dehydration and carbonization, insoluble in benzene and toluene. generating p-cresol when alkali fusion.
Commonly, p-Toluenesulfonic acid (PTSA) or tetrahydrate (TsOH4H2O) is preferred.
Preparation of methyl p-cresol acid in industry is by using concentrated sulfuric acid on the toluene sulfonation of p-toluenesulfonic acid.
The preparated p-Toluenesulfonic acid (PTSA) often contains benzene sulfonic acid and sulfuric acid impurities, can be purified in recrystallization of concentrated hydrochloric acid, azeotropic drying.
p-Toluenesulfonic acid (PTSA) is widely used as catalyst agent in the synthesis of pharmaceuticals, pesticides, polymerization stabilizer and organic synthesis (esters, etc.), paint intermediates and resin curing agent.
And p-Toluenesulfonic acid (PTSA) is also the commonly used acid catalyst in organic synthesis.
p-Toluenesulfonic acid (PTSA) is neutralized with sodium hydroxide and then obtains sodium p-toluene sulfonate, and react with phosphorus pentachloride, can obtains p-toluenesulfonyl chloride.
The latter used in the nucleophilic substitution reaction, also used as alcohol hydroxyl protective group.
p-CH3C6H4SO3Na + PCl5 →p-CH3C6H4SO2Cl.
The use of p-Toluenesulfonic acid (PTSA) also catalyzes the protection of dihydrofuran on the alcohol, carboxylic acid esterification, transesterification reaction, making the aldehyde generate acetal.
By p-toluenesulfonyl chloride hydrolysis derived.
Toluene can also be used as raw materials, sulfonated by sulfuric acid derived.
p-Toluenesulfonic acid (PTSA) or tosylic acid (TsOH) is an organic compound with the formula CH3C6H4SO3H.
p-Toluenesulfonic acid (PTSA) is a white solid that is soluble in water, alcohols, and other polar organic solvents.
The 4-CH3C6H4SO2- group is known as tosyl group and is often abbreviated as Ts or Tos.
Most often, TsOH refers to the monohydrate, TsOH.H2O.
p-Toluenesulfonic acid (PTSA) is a strong organic acid, about a million times stronger than benzoic acid.
p-Toluenesulfonic acid (PTSA) is one of the few strong acids that is solid and, hence, conveniently weighed.
Also, unlike some strong mineral acids (especially nitric acid, sulfuric acid, and per chloric acid), TsOH is non - oxidizing.
p-Toluenesulfonic acid (PTSA) is an arenesulfonic acid that is benzenesulfonic acid in which the hydrogen at position 4 is replaced by a methyl group.
p-Toluenesulfonic acid (PTSA) is a member of toluenes and an arenesulfonic acid.
p-Toluenesulfonic acid (PTSA) is a conjugate acid of a toluene-4-sulfonate.
p-Toluenesulfonic acid (PTSA) Chemical Properties
Melting point: 106~107℃
Boiling point: 116 °C
Density: 1.07
Vapor pressure: 69.8Pa at 20℃
Refractive index: 1.3825-1.3845
Fp: 41 °C
Storage temp.: Inert atmosphere,Room Temperature
Solubility: DMSO (Slightly), Methanol (Slightly)
Form: Solution
pka: -0.43±0.50(Predicted)
Color: Clear colorless to light yellow
Odor: pungent odor
Water Solubility: soluble
LogP: 0.41 at 25℃
CAS DataBase Reference: 104-15-4(CAS DataBase Reference)
NIST Chemistry Reference: p-Toluenesulfonic acid (PTSA) (104-15-4)
EPA Substance Registry System: p-Toluenesulfonic acid (PTSA) (104-15-4)
Colorless monoclinic sheet or columnar crystals.
Soluble in ethanol and ether, slightly soluble in water and hot benzene.
Reactions
p-Toluenesulfonic acid (PTSA) may be converted to p-toluene sulfonic anhydride by heating with phosphorus pentoxide.
When p-Toluenesulfonic acid (PTSA) is heated with acid and water, a hydrolysis reaction takes place and toluene is formed:
CH3C6H4SO3H + H2O → C6H5CH3 + H2SO4
This reaction is general for aryl sulfonic acids, but the rate at which it occurs depends upon the structure of the acid, the temperature and the nature of the catalyzing acid.
For example p-Toluenesulfonic acid (PTSA) is unaffected by cold concentrated hydrochloric acid, but hydrolyzes when heated to 186°C in concentrated phosphoric acid.
p-Toluenesulfonic acid (PTSA) is prepared on an industrial scale by the sulfonation of toluene.
Common impurities include benzenesulfonic acid and sulfuric acid.
p-Toluenesulfonic acid (PTSA) is most often supplied as the monohydrate, and it may be necessary to remove the complexed water before use.
Impurities can be removed by recrystallization from its concentrated aqueous solution followed by azeotropic drying with toluene.
p-Toluenesulfonic acid (PTSA) finds use in organic synthesis as an "organic-soluble" strong acid.
Examples of uses include:
Acetalization of an aldehyde
Fischer–Speier esterification
Transesterification reactions
Uses
p-Toluenesulfonic acid (PTSA) is used in the synthesis of resveratrol.
Also used in the synthesis of oxane derivatives as antimalarial agents.
(1) For chemical reagents, but also for dyes, organic synthesis.
(2) Used as the intermediates of medicine (such as doxycycline), pesticides (such as dicofol), dyes.
Also used in detergents, plastics, coatings and so on.
(3) For medicine, pesticides, dyes and detergents, but also for plastics and printing coatings.
(4) Widely used in the catalyst synthetic medicine, pesticides, polymerization of the stabilizer and organic synthesis (esters, etc.).
Also used as medicine, paint intermediates and resin curing agent.
