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Thiosalicylic acid

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Thiosalicylic acid Basic information

Product Name:
Thiosalicylic acid
Synonyms:
  • O-MERCAPTOBENZOIC ACID
  • O-SULFHYDRYLBENZOIC ACID
  • THIOSALYCYLIC ACID
  • THIOSALICYLIC ACID
  • 2-THIOSALICYLIC ACID
  • 2-MERCAPTOBENZOIC ACID
  • 2-Metrcaptobenzoic acid, o-Sulfhylbenzoic acid
  • Thisosalicyilic acid
CAS:
147-93-3
MF:
C7H6O2S
MW:
154.19
EINECS:
205-704-3
Product Categories:
  • Building Blocks
  • Chemical Synthesis
  • Aromatics
  • Organic Building Blocks
  • Sulfur Compounds
  • Thiols/Mercaptans
  • Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
  • Phenol&Thiophenol&Mercaptan
  • Metal Isotopes
  • Sulfur & Selenium Compounds
Mol File:
147-93-3.mol
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Thiosalicylic acid Chemical Properties

Melting point:
162-165 °C (lit.)
Boiling point:
247.55°C (rough estimate)
Density 
1.49
refractive index 
1.5100 (estimate)
Flash point:
150 °C
storage temp. 
Store below +30°C.
solubility 
DMSO (Slightly), Methanol (Slightly)
pka
pK1:4.05(0) (20°C)
form 
Fine Crystalline Powder
color 
White to yellow
Water Solubility 
soluble in hot water
Sensitive 
Air & Light Sensitive
Merck 
14,9360
BRN 
508507
InChIKey
NBOMNTLFRHMDEZ-UHFFFAOYSA-N
LogP
2.390
CAS DataBase Reference
147-93-3(CAS DataBase Reference)
NIST Chemistry Reference
Benzoic acid, 2-mercapto-(147-93-3)
EPA Substance Registry System
Benzoic acid, 2-mercapto- (147-93-3)
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Safety Information

Hazard Codes 
Xi,Xn,N
Risk Statements 
36/37/38-20/21/22
Safety Statements 
26-36/37/39-36
WGK Germany 
3
RTECS 
DH3325000
9-23
TSCA 
Yes
HS Code 
29309070
Hazardous Substances Data
147-93-3(Hazardous Substances Data)
Toxicity
mouse,LD50,intraperitoneal,50mg/kg (50mg/kg),National Technical Information Service. Vol. AD277-689,

MSDS

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Thiosalicylic acid Usage And Synthesis

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/ja00184a038
Chemical 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.]

Thiosalicylic acid Preparation Products And Raw materials

Preparation Products

Raw materials

Thiosalicylic acidSupplier

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