Thiosalicylic acid

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

Skeletal formula of thiosalicylic acid Space-filling model of thiosalicylic acid
Names
Preferred IUPAC name 2-Sulfanylbenzoic acid[1]
Other names 2-Mercaptobenzoic acid o-Thiosalicylic acid ortho-Thiosalicylic acid
Identifiers
CAS Number	147-93-3 Y
3D model (JSmol)	Interactive image Interactive image
Beilstein Reference	508507
ChEBI	CHEBI:59124 Y
ChEMBL	ChEMBL119888 Y
ChemSpider	5248 Y
ECHA InfoCard	100.005.187
EC Number	205-704-3
Gmelin Reference	3838
KEGG	D08586 Y
MeSH	2-Thiosalicylic+acid
PubChem CID	5443
RTECS number	DH3325000
UNII	CIP6LXN5XW Y
CompTox Dashboard (EPA)	DTXSID4049032
InChI InChI=1S/C7H6O2S/c8-7(9)5-3-1-2-4-6(5)10/h1-4,10H,(H,8,9) Y Key: NBOMNTLFRHMDEZ-UHFFFAOYSA-N Y
SMILES OC(=O)C1=CC=CC=C1S SC1=C(C(O)=O)C=CC=C1
Properties
Chemical formula	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:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Related compounds
Related compounds	Salicylic acid Thiophenol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Preparation

Thiosalicylic acid can be prepared from anthranilic acid via diazotization followed by the addition of sodium sulfide and then reduction with zinc.^[4]

Uses

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.

References

1. "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 697. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. The prefixes 'mercapto' (–SH), and 'hydroseleno' or selenyl (–SeH), etc. are no longer recommended.
2. "A13401 Thiosalicylic acid, 98%". Alfa Aesar. Retrieved 2010-08-10.
3. Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. p. 3-324. ISBN 978-1-4200-9084-0.
4. C. F. H. Allen; D. D. MacKay (1932). "Thiosalicylic acid". Organic Syntheses. 12: 76. doi:10.15227/orgsyn.012.0076.
5. Smalley, Keiran S.M.; Tim G. Eisen (1 April 2002). "Farnesyl thiosalicylic acid inhibits the growth of melanoma cells through a combination of cytostatic and pro-apoptotic effects". International Journal of Cancer. 98 (4): 514–522. doi:10.1002/ijc.10213. PMID 11920610. S2CID 11196111.
6. George, Jacob; Arnon Afek; Pnina Keren; Itzhak Herz; Iris Goldberg; Roni Haklai; Yoel Kloog; Gad Keren (2002). "Functional Inhibition of Ras by S-trans,trans-Farnesyl Thiosalicylic Acid Attenuates Atherosclerosis in Apolipoprotein E Knockout Mice". Circulation. 105 (20): 2416–2422. doi:10.1161/01.CIR.0000016065.90068.96. PMID 12021230.