p-Toluenesulfonic acid

Base Information

• Chemical Name: p-Toluenesulfonic acid
• CAS No.: 104-15-4
• Deprecated CAS: 100901-72-2,114213-96-6,126033-27-0,128739-80-0,144647-92-7,156627-46-2,210357-81-6,402-47-1,185568-48-3,227313-49-7,369371-25-5,51506-29-7,613262-31-0,1023356-14-0,119314-18-0,25231-46-3,1023356-14-0,114213-96-6,126033-27-0,128739-80-0,144647-92-7,156627-46-2,185568-48-3,210357-81-6,227313-49-7,25231-46-3,369371-25-5,402-47-1,51506-29-7,613262-31-0,633305-48-3
• Molecular Formula: C7H8O3S
• Molecular Weight: 172.205
• Hs Code.: 2904.90
• European Community (EC) Number: 203-180-0
• ICSC Number: 0773
• NSC Number: 167068,2167
• UN Number: 2584,2585
• UNII: QGV5ZG5741
• DSSTox Substance ID: DTXSID0026701
• Nikkaji Number: J5.025C
• Wikipedia: P-Toluenesulfonic_acid
• Wikidata: Q285878
• Metabolomics Workbench ID: 51481
• ChEMBL ID: CHEMBL541253
• Mol file: 104-15-4.mol

Synonyms: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;p-Methylbenzenesulfonic acid;Benzenesulfonic acid, 4-methyl-;p-Methylphenylsulfonic acid;Eltesol;p-Toluenesulfonate;Methylbenzenesulfonic acid;Cyclophil P T S A;ar-Toluenesulfonic acid;p-Toluolenesulfonic acid;PARA-TOLUENE SULFONATE;PTSA;Toluene sulfonic acid;Toluene-4-sulphonic acid;p-Toluene sulfonate;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;Kyselina p-toluensulfonova;K-Cure 1040;Toluen-4-sulfonsaeure;K-Cure 040;HSDB 2026;Toluene-p-sulfonate;Toluenesulfonic acid (VAN);NSC 167068;p-toluene sulphonic acid;para-toluenesulfonic acid;Eltesol TSX;EINECS 203-180-0;UNII-QGV5ZG5741;BRN 0472690;p-toluensulfonic acid;QGV5ZG5741;2(Or 4)-toluenesulphonic acid;DTXSID0026701;CHEBI:27849;AI3-26478;toluene-p-sulfonic acid;p-Toluene-sulfonic acid;Kyselina p-toluensulfonova [Czech];Kyselina p-toluenesulfonova [Czech];NSC-2167;para-toluenesulphonic acid;paratoluene sulphonic acid;para toluene sulfonic 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;4-methylbenzene-1-sulfonic acid;EC 203-180-0;4-11-00-00241 (Beilstein Handbook Reference);AD-3302W;KC-1040;TsOH;C-250;WLN: WSQR D1;p-TSA;TSU;LISINOPRIL IMPURITY B (EP IMPURITY);LISINOPRIL IMPURITY B [EP IMPURITY];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);SULTAMICILLIN IMPURITY B [EP IMPURITY];TIZANIDINE HYDROCHLORIDE IMPURITY I (EP IMPURITY);TIZANIDINE HYDROCHLORIDE IMPURITY I [EP IMPURITY];TosicAcid;4-sulphotoluene;pTsOH;TosOH;Tosic acid p-TSA;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;Ts-OH;p-toluen sulfonic acid;p-toluenesuiphonic acid;p-toluenylsulfonic acid;paratoluenesulfonic acid;PTS 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;TAP (CHRIS Code);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;Toluene- 4- sulphonic acid;4-methylbenzenesulphonic acid;4-methyl-benzenesulfonic acid;4-methylbenzene sulfonic acid;4-methylbenzene-sulfonic acid;70788-37-3;4-methyl benzene sulfonic acid;Acide tolunesulfonique (para-);ar-Toluenesulfonic acid (8CI);4-methyl-benzene sulphonic acid;4-methyl-benzene-sulphonic acid;2-(or 4)-Toluenesulphonic acid;NSC2167;PTS-100;4-Toluenesulfinic acid sodium salt;P-TOLUENESULFONIC ACID [MI];EINECS 274-893-2;Tox21_202364;AC-794;BDBM50294029;MFCD00064387;MFCD02683442;NSC167068;STL199173;TOLUENE SULFONIC ACID [INCI];AKOS008966288;AM90497;AT27303;CS-W019626;DB03120;Benzenesulfonic acid, 2(or 4)-methyl-;NCGC00248146-01;NCGC00248146-02;NCGC00248146-03;NCGC00259913-01;AS-82150;BP-31081;CAS-104-15-4;LS-154156;FT-0648905;T0267;C06677;A800907;AE-848/00887005;Q285878;SR-01000944854;J-001117;Q-200514;SR-01000944854-1;Toluene sulfonic acid (INCI) 4-Toluenesulfonic acid;F1908-0079

Chemical Property of p-Toluenesulfonic acid

Chemical Property:

• Appearance/Colour: clear colorless to light yellow solution
• Vapor Pressure: 69.8Pa at 20℃
• Melting Point: 106~107 °C
• Refractive Index: 1.3825-1.3845
• Boiling Point: 116 °C
• PKA: -0.43±0.50(Predicted)
• Flash Point: 41 °C
• PSA: 62.75000
• Density: 1.34 g/cm³
• LogP: 2.32250
• Storage Temp.: Flammables area
• Water Solubility.: soluble
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 172.01941529
• Heavy Atom Count: 11
• Complexity: 206
• Transport DOT Label: Corrosive

Purity/Quality:

98%min ^*data from raw suppliers

p-Toluenesulfonic acid monohydrate 98 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-10
• Safety Statements: 45-26-23

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Benzenesulfonic Acid Derivatives
• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)O
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed, especially if powdered.
• Effects of Short Term Exposure: The substance is corrosive to the eyes, skin and respiratory tract. Corrosive on ingestion. Inhalation of the aerosol may cause lung oedema. Medical observation is indicated.
• Uses: (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.
• Production method: By p-toluenesulfonyl chloride hydrolysis derived. Toluene can also be used as raw materials, sulfonated by sulfuric acid derived.
• Description: p-Toluene sulfonic acid (PTSA) or tosylic acid (TsOH) is an organic compound with the formula CH3C6H4SO3H. It 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. TsOH is a strong organic acid, about a million times stronger than benzoic acid. It 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.

Technology Process of p-Toluenesulfonic acid

There total 381 articles about p-Toluenesulfonic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

toluene (108-88-3,15644-74-3,16713-13-6) → 3-methylphenylsulfonyl chloride (1899-93-0) + m-toluenesulfonic acid (617-97-0) + o-toluenesulfonic acid (88-20-0) + toluene-4-sulfonic acid (104-15-4) + p-toluenesulfonyl chloride (98-59-9) + Toluene-2-sulfonyl chloride (133-59-5)

Guidance literature:

With chlorosulfonic acid; at 25 ℃; for 1.5h; Product distribution;

Reference yield:

4-nitrophenyl 4-methylbenzenesulfonate (1153-45-3) + 4-chlorobenzylamine (104-86-9) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + N-(4-chlorobenzyl)-p-toluenesulfonamide (10504-98-0) + toluene-4-sulfonic acid (104-15-4) + N-(4-chlorobenzyl)-4-nitroaniline

Guidance literature:

In acetonitrile; at 65 ℃; Kinetics;

DOI:10.1021/jo0161835

Reference yield:

4-nitrophenyl 4-methylbenzenesulfonate (1153-45-3) + 4-methoxy-benzylamine (2393-23-9) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + N-[(4-methoxyphenyl)methyl]-4-methylbenzenesulfonamide (54879-64-0) + toluene-4-sulfonic acid (104-15-4) + N-[(4-methoxyphenyl)methyl]-4-nitroaniline

Guidance literature:

In acetonitrile; at 65 ℃; Kinetics;

DOI:10.1021/jo0161835

upstream raw materials:

p-toluene sulfinic acid

4-methylbenzene diazonium

diethyl ether

di(4-methyl)phenylthiosulfonate

Downstream raw materials:

ethyl α-p-toluenesulfonyloxyacetate

2,2,6-trimethyl-4H-1,3-dioxin-4-one

ethyl 2-ethoxyethanoate

(+/-)-trans-3-(toluene-4-sulfonyloxy)-1,2,3,4-tetrahydro-[2]naphthol

Refernces

• 1、 Um, Ik-Hwan,Chun, Sun-Mee,Chae, Ok-Mi,Fujio, Mizue,Tsuno, Yuho. "Effect of Amine Nature on Reaction Rate and Mechanism in Nucleophilic Substitution Reactions of 2,4-Dinitrophenyl X-Substituted Benzenesulfonates with Alicyclic Secondary Amines". . p. 3166 - 3172. Retrieved 2004.
• 2、 Lee, Claire,Helmy, Roy,Strulson, Christopher,Plewa, Jolanta,Kolodziej, Elizabeth,Antonucci, Vincent,Mao, Bing,Welch, Christopher J.,Ge, Zhihong,Al-Sayah, Mohammad A.. "Removal of electrophilic potential genotoxic impurities using nucleophilic reactive resins". . p. 1021 - 1026. Retrieved 2010.
• 3、 Hisada et al.. "-". . p. 2814. Retrieved 1972.
• 4、 Zheng, Zhi,Wang, Jianli,Lu, Zhen,Luo, Min,Zhang, Miao,Xu, Lixin,Ji, Jianbing. "Hydrogenolysis of 2-tosyloxy-1,3-propanediol into 1,3-propanediol over Raney Ni catalyst". . p. 385 - 391. Retrieved 2013.
• 5、 Thea, Sergio,Vigo, Daniele,Cevasco, Giorgio. "The quest for sulfoquinone imine intermediates in the reaction of sulfanilic acid derivatives with nucleophiles". . p. 611 - 614. Retrieved 2002.
• 6、 Shefer, Neta,Carmeli, Mira,Rozen, Shlomo. "General, fast, and high yield oxidation of thiols and disulfides to sulfonic and sulfinic acids using HOF·CH3CN". . p. 8178 - 8181. Retrieved 2007.
• 7、 Fritz,Gillette. "-". . p. 1777,1778. Retrieved 1968.
• 8、 Smith, Keith,Hou, Duanjie. "A general and efficient method for the preparation of organic sulfonic acids by insertion of sulfur trioxide into the metal-carbon bond of organolithiums". . p. 1530 - 1532. Retrieved 1996.
• 9、 Chen, Ling-Jen,Burka, Leo T.. "Formation of o-nitrosobenzaldehyde from hydrolysis of o-nitrobenzyl tosylate. Evidence of intramolecular nucleophilic interaction". . p. 5351 - 5354. Retrieved 1998.
• 10、 Challenger,Kipping. "". . p. 773. Retrieved 1910.