Thiosalicylic acid

Base Information

• Chemical Name: Thiosalicylic acid
• CAS No.: 147-93-3
• Deprecated CAS: 860499-02-1
• Molecular Formula: C7H6O2S
• Molecular Weight: 154.189
• Hs Code.: 2930.90
• European Community (EC) Number: 205-704-3
• NSC Number: 660640,2184
• UNII: CIP6LXN5XW
• DSSTox Substance ID: DTXSID4049032
• Nikkaji Number: J5.842D
• Wikipedia: Thiosalicylic_acid
• Wikidata: Q1312775
• NCI Thesaurus Code: C87327
• Metabolomics Workbench ID: 60416
• ChEMBL ID: CHEMBL119888
• Mol file: 147-93-3.mol

Synonyms:2-mercaptobenzoic acid;2-sulfanylbenzoic acid;thiosalicylic acid

Chemical Property of Thiosalicylic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.00979mmHg at 25°C
• Melting Point: 162-165 °C(lit.)
• Refractive Index: 1.5100 (estimate)
• Boiling Point: 298.6 °C at 760 mmHg
• PKA: pK1:4.05(0) (20°C)
• Flash Point: 134.4 °C
• PSA: 76.10000
• Density: 1.345 g/cm³
• LogP: 1.67350
• Storage Temp.: 0-6°C
• Sensitive.: Air & Light Sensitive
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: soluble in hot water
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 154.00885060
• Heavy Atom Count: 10
• Complexity: 136

Purity/Quality:

99% ^*data from raw suppliers

Thiosalicylic Acid >90.0%(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, Xn, N
• Hazard Codes: Xi,Xn,N
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36/37/39-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Benzoic Acid Derivatives
• Canonical SMILES: C1=CC=C(C(=C1)C(=O)O)S
• Uses: Thiosalicylic acid acts as a trapping agent, which is useful in the desulfenylation of 3-indolyl sulfides. It is used to prepare macrocyclic diamides by condensation with diamines. Further, it is used as a precursor to drug, which finds application for the treatment of atherosclerosis and melanoma. In addition to this, it is involved in the preparation of vaccine preservative thiomersal and thioindigo dyestuff.

Technology Process of Thiosalicylic acid

There total 63 articles about Thiosalicylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

2-Iodobenzoic acid (88-67-5) → Thiosalicylic acid (147-93-3)

Guidance literature:

2-Iodobenzoic acid; With copper(l) iodide; potassium carbonate; sulfur; In N,N-dimethyl-formamide; at 90 ℃; for 12h; Inert atmosphere;

With sodium tetrahydroborate; In N,N-dimethyl-formamide; at 40 ℃; Inert atmosphere; Cooling with ice;

DOI:10.1021/ol902186d

Reference yield: 85.0%

2,2'-dithiobenzoic acid (119-80-2) → Thiosalicylic acid (147-93-3)

Guidance literature:

With hydrogenchloride; hydrogen iodide; hypophosphorous acid; for 3h; Heating;

Reference yield: 51.0%

2-phenylbenzo[d]-1,3-oxathiin-4-one (5651-35-4) + sodium phenoxide (139-02-6) → diphenyl 2,2'-disulfanediyldibenzoate (29585-74-8) + benzaldehyde (100-52-7) + Thiosalicylic acid (147-93-3)

Guidance literature:

In benzene; for 9h; Heating;

upstream raw materials:

2-thiocyanatobenzoic acid

3H-1,2-benzodithiol-3-one

2,2-dimethylthiochromone

1-thioflavone

Downstream raw materials:

2-thiophen-2-ylsulfanyl-benzoic acid

2-(2,5-dimethyl-[3]thienylmercapto)-benzoic acid

2-(5-nitro-[2]pyridylmercapto)-benzoic acid

2-(2,5-dioxo-1-phenyl-pyrrolidin-3-ylmercapto)-benzoic acid

Refernces

• 1、 Fife, Thomas H.,Przystas, Theodore J.. "Intramolecular Electrostatic and General Acid Catalysis in the Hydrolysis of O,S-Thioacetals". . p. 292 - 299. Retrieved 1980.
• 2、 Wang, Shengzheng,Fang, Kun,Dong, Guoqiang,Chen, Shuqiang,Liu, Na,Miao, Zhenyuan,Yao, Jianzhong,Li, Jian,Zhang, Wannian,Sheng, Chunquan. "Scaffold Diversity Inspired by the Natural Product Evodiamine: Discovery of Highly Potent and Multitargeting Antitumor Agents". . p. 6678 - 6696. Retrieved 2015/09/07.
• 3、 Xu, Hua-Jian,Liang, Yu-Feng,Cai, Zhen-Ya,Qi, Hong-Xia,Yang, Chun-Yan,Feng, Yi-Si. "CuI-nanoparticles-catalyzed selective synthesis of phenols, anilines, and thiophenols from aryl halides in aqueous solution". experimental part. p. 2296 - 2300. Retrieved 2011/06/17.