147-93-3 Usage
Chemical Description
Thiosalicylic acid is a derivative of salicylic acid and is used in the synthesis of various compounds.
Description
Thiosalicylic acid, also known as 2-mercaptobenzoic acid, is a sulfanylbenzoic acid that is the 2-sulfanyl derivative of benzoic acid. It is a sulfur-yellow solid with a melting point of 164 °C (327 °F) and exhibits properties such as sublimation, slight solubility in hot water, and free solubility in glacial acetic acid and alcohol. Thiosalicylic acid has a role as a non-narcotic analgesic and an antipyretic, and it can yield dithiosalicylic acid upon exposure to air.
Uses
Used in Pharmaceutical Industry:
Thiosalicylic acid is used as a precursor to drugs, particularly for the treatment of atherosclerosis and melanoma. It serves as a starting material for the synthesis of various pharmaceutical compounds.
Used in Chemical Synthesis:
Thiosalicylic acid is used as a nucleophilic trapping agent for the desulfenylation of 3-indolyl sulfides to obtain 3-unsubstituted indoles. It is also a starting material to prepare 2′-mercaptoacetophenone, which is used in the synthesis of thioflavanone by reacting with lithium diisopropylamide and benzaldehyde.
Used in Material Science:
Thiosalicylic acid acts as a stabilizing agent in the synthesis of metal nanoparticles, contributing to the development of advanced materials with various applications.
Used in Dye Industry:
It is involved in the preparation of thioindigo dyestuff, which is used in the production of pigments and dyes for various industries.
Used in Vaccine Preservation:
Thiosalicylic acid is used in the preparation of vaccine preservative thiomersal, which plays a crucial role in maintaining the stability and safety of vaccines.
Preparation
Thiosalicylic acid can be prepared from anthranilic acid via diazotization followed by the addition of sodium sulfide and then reduction with zinc. It can also prepared by heating o-halogenated benzoic acids with alkaline hydrosulfide in presence of copper.
Synthesis Reference(s)
Journal of the American Chemical Society, 111, p. 654, 1989 DOI: 10.1021/ja00184a038Chemical and Pharmaceutical Bulletin, 33, p. 5184, 1985 DOI: 10.1248/cpb.33.5184
Purification Methods
Crystallise the thio acid from hot EtOH (4mL/g), after adding hot distilled water (8mL/g) and boiling with charcoal. The hot solution is filtered, cooled, the solid is collected and dried in vacuo (P2O5). Crystallise it from AcOH and sublime in vacuo.[Beilstein 10 IV 272.]
Check Digit Verification of cas no
The CAS Registry Mumber 147-93-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,4 and 7 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 147-93:
(5*1)+(4*4)+(3*7)+(2*9)+(1*3)=63
63 % 10 = 3
So 147-93-3 is a valid CAS Registry Number.
InChI:InChI=1/C7H6O2S/c8-7(9)5-3-1-2-4-6(5)10/h1-4,8-9H/p-2
147-93-3Relevant articles and documents
First electrospun immobilized molybdenum complex on bio iron oxide nanofiber for green oxidation of alcohols
Noghi, Sedighe Abbaspour,Naeimi, Atena,Hamidian, Hooshang
, p. 229 - 237 (2018)
Bio iron oxide was synthesized from natural Sesbania sesban plant and modified by a molybdenum complex (Fe2O3/MoSB). Fe2O3/MoSB was deposited on polyvinyl alcohol (PVA) using a conventional single nozzle electrospinning technique (PVA/Fe2O3/MoSB). TEM, SEM, AFM, FT-IR, TGA, EDAX, and elemental analysis were used to determine fiber compositional information. The catalytic efficiency of electrospun PVA/Fe2O3/MoSB nanofiber in the oxidation of alcohols was exploited. The green reactions were conducted at solvent free conditions as a green media in the presence of H2O2 to have the desired aldehydes and tert-butyl hydrogen peroxide to obtain acid products in high yields and excellent selectivity. The survival of this nanocomposite was investigated and it could be reused and recycled in consecutive runs.
Efficient Cu-catalyzed base-free C-S coupling under conventional and microwave heating. A simple access to S-heterocycles and sulfides
Soria-Castro, Silvia M.,Penenory, Alicia B.
, p. 467 - 475 (2013/05/08)
S-aryl thioacetates can be prepared by reaction of inexpensive potassium thioacetate with both electron-rich and electron-poor aryl iodides under a base-free copper/ligand catalytic system. CuI as copper source affords S-aryl thioacetates in good to excellent yields, by using 1,10-phenanthroline as a ligand in toluene at 100°C after 24 h. Under microwave irradiation the time was drastically reduced to 2 h. Both procedures are simple and involve a low-cost catalytic system. This methodology was also applied to the "one-pot" synthesis of target heterocycles, such as 3H-benzo[c][1,2]dithiol-3-one and 2-methylbenzothiazole, alkyl aryl sulfides, diaryl disulfides and asymmetric diaryl sulfides in good yields.
Electromediators in synthesis of sulfur organic compounds based on hydrogen sulfide and thiols
Okhlobystin,Okhlobystina,Shinkar',Berberova,Eremenko
body text, p. 302 - 306 (2011/10/07)
-