| Identification | More | [Name]
Thiosalicylic acid | [CAS]
147-93-3 | [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- | [EINECS(EC#)]
205-704-3 | [Molecular Formula]
C7H6O2S | [MDL Number]
MFCD00004836 | [Molecular Weight]
154.19 | [MOL File]
147-93-3.mol |
| Chemical Properties | Back Directory | [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 | [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]
147-93-3(EPA Substance) |
| Safety Data | Back Directory | [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 . | [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 . | [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 Information | Back Directory | [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. | [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.] |
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