147-93-3 Usage
Chemical Description
Thiosalicylic acid is a derivative of salicylic acid and is used in the synthesis of various compounds.
Chemical Properties
Thiosalicylic acid, (o-mercapto benzoic acid), a sulfur-yellow solid that softens at 158 °C (316 °F), has a melting point of 164 °C (327 °F). It sublimes, is slightly soluble in hot water but freely soluble in glacial acetic acid and alcohol, and yields dithiosalicylic acid, upon exposure to air.
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.
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.
Application
thiosalicylic acid can be used as:A nucleophilic trapping agent for the desulfenylation of 3-indolyl sulfides to obtain 3-unsubstituted indoles.A starting material to prepare 2′-mercaptoacetophenone, which is used in the synthesis of thioflavanone by reacting with lithium diisopropylamide and benzaldehyde.A stabilizing agent in the synthesis of metal nanoparticles.It can also be used to prepare 2-thioxanthone-thioacetic acid bimolecular system, which is used as a photoinitiator for free radical polymerization.
Definition
ChEBI: Thiosalicylic acid is a sulfanylbenzoic acid that is the 2-sulfanyl derivative of benzoic acid. It has a role as a non-narcotic analgesic and an antipyretic. It is a conjugate acid of a thiosalicylate(1-).
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)
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