Thiosalicylic acid Property

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)

Safety

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

F 

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,

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Thiosalicylic acid Chemical Properties,Usage,Production

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.]