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| | Thiosalicylic acid Basic information |
| | Thiosalicylic acid Chemical Properties |
| Melting point | 162-165 °C (lit.) | | Boiling point | 247.55°C (rough estimate) | | density | 1.49 | | refractive index | 1.5100 (estimate) | | Fp | 150 °C | | storage temp. | Store below +30°C. | | solubility | DMSO (Slightly), Methanol (Slightly) | | pka | pK1:4.05(0) (20°C) | | form | Fine Crystalline Powder | | color | White to yellow | | Water Solubility | soluble in hot water | | Sensitive | Air & Light Sensitive | | Merck | 14,9360 | | BRN | 508507 | | InChIKey | NBOMNTLFRHMDEZ-UHFFFAOYSA-N | | LogP | 2.390 | | CAS DataBase Reference | 147-93-3(CAS DataBase Reference) | | NIST Chemistry Reference | Benzoic acid, 2-mercapto-(147-93-3) | | EPA Substance Registry System | Benzoic acid, 2-mercapto- (147-93-3) |
| | Thiosalicylic acid Usage And Synthesis |
| Chemical Properties | Thiosalicylic acid, (o-mercapto benzoic acid), a sulfur-yellow solid that softens at 158 °C (316 °F), has a melting point of 164 °C (327 °F). It sublimes, is slightly soluble in hot water but freely soluble in glacial acetic acid and alcohol, and yields dithiosalicylic acid, upon exposure to air. | | Uses | Thiosalicylic acid acts as a trapping agent, which is useful in the desulfenylation of 3-indolyl sulfides. It is used to prepare macrocyclic diamides by condensation with diamines. Further, it is used as a precursor to drug, which finds application for the treatment of atherosclerosis and melanoma. In addition to this, it is involved in the preparation of vaccine preservative thiomersal and thioindigo dyestuff. | | Preparation | Thiosalicylic acid can be prepared from anthranilic acid via diazotization followed by the addition of sodium sulfide and then reduction with zinc. It can also prepared by heating o-halogenated benzoic acids with alkaline hydrosulfide in presence of copper. | | Application | thiosalicylic acid can be used as:
A nucleophilic trapping agent for the desulfenylation of 3-indolyl sulfides to obtain 3-unsubstituted indoles.
A starting material to prepare 2′-mercaptoacetophenone, which is used in the synthesis of thioflavanone by reacting with lithium diisopropylamide and benzaldehyde.
A stabilizing agent in the synthesis of metal nanoparticles.
It can also be used to prepare 2-thioxanthone-thioacetic acid bimolecular system, which is used as a photoinitiator for free radical polymerization. | | Definition | ChEBI: Thiosalicylic acid is a sulfanylbenzoic acid that is the 2-sulfanyl derivative of benzoic acid. It has a role as a non-narcotic analgesic and an antipyretic. It is a conjugate acid of a thiosalicylate(1-). | | Synthesis Reference(s) | Journal of the American Chemical Society, 111, p. 654, 1989 DOI: 10.1021/ja00184a038
Chemical and Pharmaceutical Bulletin, 33, p. 5184, 1985 DOI: 10.1248/cpb.33.5184 | | Purification Methods | Crystallise the thio acid from hot EtOH (4mL/g), after adding hot distilled water (8mL/g) and boiling with charcoal. The hot solution is filtered, cooled, the solid is collected and dried in vacuo (P2O5). Crystallise it from AcOH and sublime in vacuo.[Beilstein 10 IV 272.] |
| | Thiosalicylic acid Preparation Products And Raw materials |
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