Thiosalicylic acid

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 ;
3D model (JSmol)	Interactive image; Interactive image;
Beilstein Reference	508507
ChEBI	CHEBI:59124 ;
ChEMBL	ChEMBL119888 ;
ChemSpider	5248 ;
ECHA InfoCard	100.005.187
EC Number	205-704-3;
Gmelin Reference	3838
KEGG	D08586 ;
MeSH	2-Thiosalicylic+acid
PubChem CID	5443;
RTECS number	DH3325000;
UNII	CIP6LXN5XW ;
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) Key: NBOMNTLFRHMDEZ-UHFFFAOYSA-N ;
	SMILES OC(=O)C1=CC=CC=C1S; SC1=C(C(O)=O)C=CC=C1;
Properties
Chemical formula	C7H6O2S
Molar mass	154.18 g·mol−1
Appearance	Leaf or needle shaped 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
EU classification (DSD) (outdated)	Xi
R-phrases (outdated)	R36/37/38
S-phrases (outdated)	S26
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).
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	Infobox references

Thiosalicylic acid is an organosulfur compound containing carboxyl and sulfhydryl functional groups. Its molecular formula is C₆H₄(SH)(CO₂H). it is a yellow solid that is slightly soluble in water, ethanol and diethyl ether, and alkanes, but more soluble in DMSO.[3]

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

"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.
"A13401 Thiosalicylic acid, 98%". Alfa Aesar. Retrieved 2010-08-10.
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.
C. F. H. Allen; D. D. MacKay (1932). "Thiosalicylic acid". Organic Syntheses. 12: 76. doi:10.15227/orgsyn.012.0076.
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.
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.

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[iupac2013-1] "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.

[Alfa-2] "A13401 Thiosalicylic acid, 98%". Alfa Aesar. Retrieved 2010-08-10.

[CRC90-3] 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.

[Farnesyl-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.

[Ras-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.