HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
2-Mercaptobenzoesure
2-MERCAPTOBENZOIC ACID · Thiosalicylic · O-MERCAPTOBENZOIC ACID · 2-Thiobenzoic acid · THIOSALYCYLIC ACID · 2-Sulfanylbenzoic acid · icyiL · usafkf-2
Identifikatoren & physikalische Daten
| CAS No. | 147-93-3 |
|---|---|
| Summenformel | C7H6O2S |
| Durchschnittliche Molmasse | 154,19 g/mol |
| Monoisotopische Masse | 154,00885043 g/mol |
| SMILES | O=C(O)c1ccccc1S |
| InChIKey | NBOMNTLFRHMDEZ-UHFFFAOYSA-N |
| PubChem CID | 5443 |
| ChEMBL | CHEMBL119888 |
| ChEBI | CHEBI:59124 |
| EC No. | 205-704-3 |
| DTXSID | DTXSID4049032 |
| Lokaler Name | 2-Mercaptobenzoesure |
Chemische & physikalische Eigenschaften
| XLogP | 2,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 38,3 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 136 |
| Stoffklassen | Other Classes -> Benzoic Acid Derivatives |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| Kosmetika | AntioxidantKeratolyticReducing |
| SpringerMaterials Properties | Chemical shift |
| Color/Form | SULFUR-YELLOW FLAKES, PLATES, NEEDLES FROM GLACIAL ACETIC ACID OR ALCOHOLLEAVES OR NEEDLES FROM WATERCRYSTALS /SODIUM SALT/ |
| Löslichkeit | SOL IN WATER /SODIUM SALT/SOL IN HOT WATER, ALCOHOL, ETHER, ACETIC ACIDSLIGHTLY SOLUBLE IN PETROLEUM ETHERDMSO (Slightly), Methanol (Slightly)soluble in hot water |
| Schmelzpunkt | 168-169 °C162-165 °C (lit.) |
| Physical Description | Sulfur-yellow solidSlightly soluble in hot water[Merck Index] Yellow powder, soluble in water[MSDSonline] |
| Stability/Shelf Life | EXPOSURE TO AIR YIELDS DITHIOSALICYLIC ACID |
| Other Experimental Properties | WHEN AN ALCOHOLIC SOLN OF THIOSALICYLIC ACID COMES IN CONTACT WITH FERRIC CHLORIDE, DITHIOSALICYLIC ACID IS PRODUCEDSOFTENS AT 158 °CSUBLIMES |
| Siedepunkt | 247.55°C (rough estimate) |
| Dichte | 1.49 |
| Brechungsindex | 1.5100 (estimate) |
| Flammpunkt | 150 °C |
| Lagerbedingungen | Store below +30°C. |
| pKa (Säurekonstante) | pK1:4.05(0) (20°C) |
| Aggregatzustand | Fine Crystalline Powder |
| Farbe | White to yellow |
| Merck | 14,9360 |
| BRN | 508507 |
| Kosmetik-Inhaltsstoffe Funktionen | REDUCINGANTIOXIDANTKERATOLYTIC |
| 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 (Verteilungskoeffizient) | 2.390 |
| CAS Datenbank | 147-93-3(CAS DataBase Reference) |
| NIST chemische Informationen | Benzoic acid, 2-mercapto-(147-93-3) |
| EPA chemische Informationen | Benzoic acid, 2-mercapto- (147-93-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 50 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Benzoic acid, 2-mercapto-Thiosalicylic acid: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Skin Irrit. 2 (100%) |
| Protective Action Criteria (PAC) | 0.16 [mg/m3]1.8 [mg/m3]11 [mg/m3] |
| Non-Human Toxicity Excerpts | UNCOUPLING OF OXIDATIVE PHOSPHORYLATION IN RAT LIVER MITOCHONDRIA WAS INVESTIGATED WITH THIO ANALOGS OF SALICYLIC ACID. SIGNIFICANT ACTIVITY WAS OBSERVED. |
| F | 9-23 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29309070 |
| RTECS-Nr. | DH3325000 |
| R-Sätze (R) | 36/37/38-20/21/22 |
| Toxizität | mouse,LD50,intraperitoneal,50mg/kg (50mg/kg),National Technical Information Service. Vol. AD277-689, |
| Gefahrensymbole | Xi,Xn,N |
| Sicherheitshinweise (S) | 26-36/37/39-36 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 147-93-3(Hazardous Substances Data) |
| Gefahrenklasse | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
Anwendungen & Verwendung
Verwenden
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.
Herstellung & Synthese
synthetische
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.