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| | p-Toluenesulfonic acid monohydrate Basic information |
| | p-Toluenesulfonic acid monohydrate Chemical Properties |
| Melting point | 96-99 °C(lit.) | | Boiling point | 140°C 20mm | | bulk density | 510kg/m3 | | density | 1,24 g/cm3 | | vapor density | 5.9 (vs air) | | refractive index | 1,382-1,384 | | Fp | 180 °C | | storage temp. | Store at +5°C to +30°C. | | solubility | H2O: 0.1 g/mL, clear | | form | Solid | | Colour Index | 42655 | | color | White to pink | | PH | 1 (650g/l, H2O, 20℃)(anhydrous substance) | | Water Solubility | soluble | | Sensitive | Hygroscopic | | Merck | 14,9533 | | BRN | 3568023 | | Stability: | Stable. Incompatible with strong oxidizing agents, strong bases, most common metals. Protect from moisture. | | InChI | 1S/C7H8O3S.H2O/c1-6-2-4-7(5-3-6)11(8,9)10;/h2-5H,1H3,(H,8,9,10);1H2 | | InChIKey | KJIFKLIQANRMOU-UHFFFAOYSA-N | | SMILES | [H]O[H].Cc1ccc(cc1)S(O)(=O)=O | | CAS DataBase Reference | 6192-52-5(CAS DataBase Reference) | | EPA Substance Registry System | Benzenesulfonic acid, 4-methyl-, monohydrate (6192-52-5) |
| Hazard Codes | Xi,C | | Risk Statements | 36/37/38-34-37 | | Safety Statements | 26-37-45-36/37/39 | | RIDADR | UN 2585 8/PG 3 | | WGK Germany | - | | RTECS | XT6300000 | | F | 3 | | Autoignition Temperature | 600 °C | | TSCA | Yes | | HazardClass | 8 | | PackingGroup | III | | HS Code | 29041000 | | Storage Class | 8A - Combustible corrosive hazardous materials | | Hazard Classifications | Eye Irrit. 2
Met. Corr. 1
Skin Irrit. 2
STOT SE 3 | | Toxicity | LD50 orally in Rabbit: 2570 mg/kg |
| | p-Toluenesulfonic acid monohydrate Usage And Synthesis |
| Chemical Properties | White crystals | | Uses | Derivitizing agent. | | Uses | p-Toluenesulfonic acid monohydrate is used as a catalyst in the synthesis of resveratrol, in oxane derivatives as an antimalarial agent, as substituted piperidine and unsymmetrical benzyl. It acts as a catalyst in the preparation of 1,3,5-trisubstituted pyrazoles derivatives, selenated ketene dithioacetals, triazoloquinazolinone and benzimidazoquinazolinone derivatives. It also serves as an intermediate in the esterification and in reductive amination reactions. | | Uses | 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.
| | 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. | | Purification Methods | Purify the acid by precipitation from a saturated solution at 0o by introducing HCl gas. It can also be crystallised from conc HCl, then crystallised from dilute HCl (charcoal) to remove benzenesulfonic acid. It has been crystallised from EtOH/water. Dry it in a vacuum desiccator over solid KOH and CaCl2. p-Toluenesulfonic acid can be dehydrated by azeotropic distillation with *benzene or by heating at 100o for 4hours under water-pump vacuum. The anhydrous acid can be crystallised from *benzene, CHCl3, ethyl acetate, anhydrous MeOH, or from acetone by adding a large excess of *benzene. It can also be dried under vacuum at 50o. The S-benzylisothiuronium salt has m 182o (from aqueous EtOH). [Beilstein 11 IV 241.] | | Toxics Screening Level | The initial threshold screening levels (ITSLs) for p-toluenesulfonic acid monohydrate are 1.9 μg/m3, annual averaging time and 230 μg/m3, 1 hour averaging time. |
| | p-Toluenesulfonic acid monohydrate Preparation Products And Raw materials |
| Preparation Products | Ethyl (R)-2-hydroxy-4-phenylbutyrate-->Clemizole-->2-(3-CHLOROPROPYL)-1,3-DIOXOLANE-->4-(1,2,3-THIADIAZOL-4-YL)BENZYLAMINE HYDROCHLORIDE-->4-CHLORO-2-(TETRAHYDRO-2H-PYRAN-2-YL)-5-HYDROXYPYRIDAZIN-3(2H)-ONE-->4-(4-CHLOROPHENYL)-1,2,3-THIADIAZOL-5-AMINE-->3-METHOXYCARBONYL-3-SULFOLENE-->2-(5-METHYL-2-PHENYL-1,3-OXAZOL-4-YL)ACETIC ACID-->Cefoperazone-->4-(4-METHOXYPHENYL)-1,2,3-THIADIAZOL-5-AMINE-->4-[4-(TRIFLUOROMETHYL)PHENYL]-1,2,3-THIADIAZOL-5-AMINE-->1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone-->LENAMPICILLIN-->4-[4-(BROMOMETHYL)PHENYL]-1,2,3-THIADIAZOLE-->2-AMINO-4-METHYL-PYRIMIDINE-5-CARBOXYLIC ACID-->Saquinavir-->4-PYRIDINEETHANETHIOL HYDROCHLORIDE-->Methyl glycolate-->METHYL 4-BROMO-3-OXOPENTANOATE-->Doxifluridine-->2-Phenyl-2-imidazoline-->Pyridinium p-Toluenesulfonate |
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