Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Thiosalicylic acid: Difference between pages

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 470608986

| ImageFileL1 = Thiosalicylic-acid-2D-skeletal-B.png

| ImageFileL1_Ref = {{Chemboximage|correct|??}}

| ImageNameL1 = Skeletal formula of thiosalicylic acid

| ImageFileR1_Ref = {{Chemboximage|correct|??}}

| ImageNameR1 = Space-filling model of thiosalicylic acid

| PIN = 2-Sulfanylbenzoic acid<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Royal Society of Chemistry|The Royal Society of Chemistry]] | date = 2014 | location = Cambridge | page = 697 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4 | quote = The prefixes ‘mercapto’ (–SH), and ‘hydroseleno’ or selenyl (–SeH), etc. are no longer recommended.| chapter = Front Matter}}</ref>

| OtherNames = 2-Mercaptobenzoic acid<br />''o''-Thiosalicylic acid<br />''ortho''-Thiosalicylic acid

|Section1={{Chembox Identifiers

| CASNo = 147-93-3

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = CIP6LXN5XW

| PubChem = 5443

| ChemSpiderID = 5248

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| EINECS = 205-704-3

| KEGG = D08586

| KEGG_Ref = {{keggcite|correct|kegg}}

| MeSHName = 2-Thiosalicylic+acid

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 59124

| ChEMBL = 119888

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| RTECS = DH3325000

| Beilstein = 508507

| Gmelin = 3838

| SMILES = OC(=O)C1=CC=CC=C1S

| SMILES1 = SC1=C(C(O)=O)C=CC=C1

| StdInChI = 1S/C7H6O2S/c8-7(9)5-3-1-2-4-6(5)10/h1-4,10H,(H,8,9)

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = NBOMNTLFRHMDEZ-UHFFFAOYSA-N

}}

|Section2={{Chembox Properties

| Formula = ''ortho''-{{chem2|C6H4(SH)(COOH)}}

| C=7|H=6|O=2|S=1

| Appearance = Leaf or needle shaped yellow crystals

| Density = 1.49 g cm⁻³<ref name="Alfa">{{cite web | url = http://www.alfa.com/en/GP100W.pgm?DSSTK=A13401&rnd=224806350 | title = A13401 Thiosalicylic acid, 98% | publisher = [[Alfa Aesar]] | access-date = 2010-08-10}}</ref>

| MeltingPtC = 162 to 169

| LogP = 2.39

| pKa = 3.501

}}

|Section3={{Chembox Hazards

| GHS_ref=

| GHSPictograms = {{GHS07}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|315|319|335}}

| PPhrases = {{P-phrases|}}

}}

|Section4={{Chembox Related

| OtherCompounds = {{ubl|[[Salicylic acid]]|[[Thiophenol]]}}

'''Thiosalicylic acid''' is an [[organosulfur compound]] containing [[carboxyl]] and [[sulfhydryl]] [[functional group]]s. Its [[molecular formula]] is [[Arene substitution pattern|''ortho'']]-{{chem2|C6H4(\sSH)(\sC(\dO)\sOH)}}. It is a yellow solid that is slightly soluble in [[water]], [[ethanol]] and [[diethyl ether]], and [[alkanes]], but more soluble in [[dimethyl sulfoxide|DMSO]].<ref name="CRC90">{{CRC90|page=3-324}}</ref>

==Preparation==

Thiosalicylic acid can be prepared from [[anthranilic acid]] via [[diazotization]] followed by the addition of [[sodium sulfide]] and then reduction with [[zinc]].<ref>{{cite journal|author=C. F. H. Allen |author2= D. D. MacKay |title=Thiosalicylic acid|year=1932|volume= 12|pages= 76|doi=10.15227/orgsyn.012.0076|journal=Organic Syntheses}}</ref>

==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.<ref name=Farnesyl>{{cite journal|last=Smalley|first=Keiran S.M.|author2=Tim G. Eisen |title=Farnesyl thiosalicylic acid inhibits the growth of melanoma cells through a combination of cytostatic and pro-apoptotic effects|journal=International Journal of Cancer|date=1 April 2002|volume=98|issue=4|pages=514–522|doi=10.1002/ijc.10213|pmid=11920610|s2cid=11196111}}</ref><ref name=Ras>{{cite journal|last=George|first=Jacob|author2=Arnon Afek|author2-link=Arnon Afek|author3=Pnina Keren |author4=Itzhak Herz |author5=Iris Goldberg |author6=Roni Haklai |author7=Yoel Kloog |author8= Gad Keren |title=Functional Inhibition of Ras by S-trans,trans-Farnesyl Thiosalicylic Acid Attenuates Atherosclerosis in Apolipoprotein E Knockout Mice|journal=Circulation|year=2002|volume=105|issue=20|pages=2416–2422|doi=10.1161/01.CIR.0000016065.90068.96|pmid=12021230|doi-access=free}}</ref> The preservative [[benzisothiazolinone]] is prepared from thiosalicylic acid.

==References==

{{Reflist}}

[[Category:Benzoic acids]]

[[Category:Thiols]]