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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: | |||
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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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]
Thiosalicylic acid can be prepared from anthranilic acid via diazotization followed by the addition of sodium sulfide and then reduction with zinc. [4]
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.
The prefixes 'mercapto' (–SH), and 'hydroseleno' or selenyl (–SeH), etc. are no longer recommended.