ChemicalBook CAS DataBase List 147-93-3

147-93-3

Name	Thiosalicylic acid
CAS	147-93-3
EINECS(EC#)	205-704-3
Molecular Formula	C7H6O2S
MDL Number	MFCD00004836
Molecular Weight	154.19
MOL File	147-93-3.mol

Synonyms

2-MERCAPTOBENZOIC ACID 2-THIOSALICYLIC ACID AKOS 93572 O-MERCAPTOBENZOIC ACID O-SULFHYDRYLBENZOIC ACID THIOSALICYLIC ACID THIOSALYCYLIC ACID 2-Carboxythiophenol 2-mercapto-benzoicaci 2-Sulfanylbenzoic acid 2-thio-salicylicaci Benzoic acid, o-mercapto- o-Benzoic acid thiol o-benzoicacidthiol o-Carboxythiophenol o-Mercaptobenzoesaeure o-mercapto-benzoicaci o-Thiosalicylic acid o-thiosalicylicacid Salicylic acid, 2-thio-

Chemical Properties

Appearance	white to light yellow crystal powder
Melting point	162-165 °C (lit.)
Boiling point	247.55°C (rough estimate)
density	1.49
refractive index	1.5100 (estimate)
Fp	150 °C
storage temp.	0-6°C
solubility	DMSO (Slightly), Methanol (Slightly)
form	Fine Crystalline Powder
pka	pK1:4.05(0) (20°C)
color	White to yellow
Water Solubility	soluble in hot water
Sensitive	Air & Light Sensitive
Usage	A trapping agent used in the desulfenylation of 3-indolyl sulfides
Merck	14,9360
BRN	508507
Cosmetics Ingredients Functions	REDUCING ANTIOXIDANT KERATOLYTIC
InChI	1S/C7H6O2S/c8-7(9)5-3-1-2-4-6(5)10/h1-4,10H,(H,8,9)
InChIKey	NBOMNTLFRHMDEZ-UHFFFAOYSA-N
SMILES	OC(=O)c1ccccc1S
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	147-93-3(EPA Substance)

Safety Data

Symbol(GHS)	GHS07
Signal word	Warning
Hazard statements	H315-H319-H335
Precautionary statements	P261-P264-P271-P280-P302+P352-P305+P351+P338
Hazard Codes	Xi,Xn,N
Risk Statements	R36/37/38:Irritating to eyes, respiratory system and skin . R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . less more
Safety Statements	S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . S36:Wear suitable protective clothing . less more
WGK Germany	3
RTECS	DH3325000
F	9-23
TSCA	Yes
HS Code	29309070
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3
Hazardous Substances Data	147-93-3(Hazardous Substances Data)
Toxicity	mouse,LD50,intraperitoneal,50mg/kg (50mg/kg),National Technical Information Service. Vol. AD277-689, less more

Raw materials And Preparation Products

Hazard Information

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.

Chemical Properties

white to light yellow crystal powder

Uses

A trapping agent used in the desulfenylation of 3-indolyl sulfides

Uses

Thiosalicylic acid can be used as trapping agent in the desulfenylation of 3-indolyl sulfides and used to condense with diamines to form macrocyclic diamides.

Uses

Trapping agent used in the desulfenylation of 3-indolyl sulfides.1 Condenses with diamines to form macrocyclic diamides.2

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: A sulfanylbenzoic acid that is the 2-sulfanyl derivative of benzoic acid.

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.

Reactions

Hydroxythioxanthones are readily obtained with good regioselectivity from the reaction of thiosalicylic acid with phenols effected by a mixture of methanesulfonic acid and alumina.

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.]

Material Safety Data Sheet(MSDS)

Spectrum Detail

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