Thiosalicylic acid
Chemical compound
From Wikipedia, the free encyclopedia
Thiosalicylic acid is an organosulfur compound containing carboxyl and sulfhydryl functional groups. Its molecular formula is ortho-C6H4(−SH)(−C(=O)−OH). It is a yellow solid that is slightly soluble in water, ethanol and diethyl ether, and alkanes, but more soluble in DMSO.[3]
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| Names | |||
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| Preferred IUPAC name
2-Sulfanylbenzoic acid[1] | |||
| Other names
2-Mercaptobenzoic acid o-Thiosalicylic acid ortho-Thiosalicylic acid | |||
| Identifiers | |||
3D model (JSmol) |
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| 508507 | |||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider | |||
| ECHA InfoCard | 100.005.187 | ||
| EC Number |
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| 3838 | |||
| KEGG | |||
| MeSH | 2-Thiosalicylic+acid | ||
PubChem CID |
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| RTECS number |
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| UNII | |||
CompTox Dashboard (EPA) |
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| Properties | |||
| ortho-C6H4(SH)(COOH) | |||
| Molar mass | 154.18 g·mol−1 | ||
| Appearance | Leaf or needle shaped yellow crystals | ||
| Density | 1.49 g cm−3[2] | ||
| Melting point | 162 to 169 °C (324 to 336 °F; 435 to 442 K) | ||
| log P | 2.39 | ||
| Acidity (pKa) | 3.501 | ||
| Hazards | |||
| GHS labelling: | |||
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| Warning | |||
| H315, H319, H335 | |||
| Related compounds | |||
Related compounds |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Preparation
Thiosalicylic acid can be prepared from anthranilic acid via diazotization followed by the addition of sodium sulfide and then reduction with zinc.[4]
Applications
Thiosalicylic acid is a precursor to the dyestuff thioindigo. It is also used to make the vaccine preservative thiomersal. It is a precursor to drug candidates for treatment of atherosclerosis and melanoma.[5][6] The preservative benzisothiazolinone is prepared from thiosalicylic acid.
Thiosalicylic acid is an excellent ligand, able to coordinate a very wide range of metals.[7]