16854-67-4

Basic information

• Product Name: 4-Hydroxylthiocoumarin
• Synonyms: 4-HYDROXY-2H-THIOCHROMEN-2-ONE;AKOS AU-SVL-37-03;CHEMBRDG-BB 5102960;4-Hydroxy thiocoumarin;4-hydroxy-2H-benzothiopyran-2-one;4-Hydroxythiocoumarin;4-HYDROXYLTHIOCOUMARIN;4-hydroxy-2H-benzothiopyran-2-one，4-hydroxyl-thio-coumarin
• CAS NO: 16854-67-4
• Molecular Formula: C₉H₆O₂S
• Molecular Weight: 178.21
• Mol File: 16854-67-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 209 °C(Solv: water (7732-18-5))
• Boiling Point: 307.4 °C at 760 mmHg
• Flash Point: 139.7 °C
• Appearance: /
• Density: 1.478 g/cm³
• Vapor Pressure: 0.000315mmHg at 25°C
• Refractive Index: 1.726
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.50±1.00(Predicted)
• CAS DataBase Reference: 4-Hydroxylthiocoumarin(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxylthiocoumarin(16854-67-4)
• EPA Substance Registry System: 4-Hydroxylthiocoumarin(16854-67-4)

Safety Data

• Hazardous Substances Data: 16854-67-4(Hazardous Substances Data)

Usage

Uses

4-?Hydroxy-2H-?1-?benzothiopyran-?2-?one is an intermediate in synthesizing Difethialone (D445450), is an anticoagulant rodenticide widely used to control rodent infestations.

InChI:InChI=1/C9H6O2S/c10-7-5-9(11)12-8-4-2-1-3-6(7)8/h1-5,11H

Upstream product

• 75-44-5 phosgene 
• 26824-02-2 1-(2-mercaptophenyl)ethan-1-one 
• 62972-22-9 S-acetylthiosalicylic acid chloride 
• 273380-14-6 diethyl 2-(2-acetylmercapto)benzoylmalonate 
• 55819-78-8 2-acetylmercaptobenzoic acid 
• 108-98-5 thiophenol 
• 16854-72-1 Dithiomalonsaeure-S,S'-diphenylester 
• 105-58-8 Diethyl carbonate 
• 616-38-6 carbonic acid dimethyl ester 

Downstream Products

• 29266-68-0 1,2-benzisothiazole-3-acetic acid 
• 13723-12-1 3,3'-(phenylmethylene)bis(4-hydroxy-2H-thiochromen-2-one) 
• 1400990-20-6 (R)-2-(3-(4-hydroxy-2-oxo-2H-thiochromen-3-yl)-3-phenylpropanoyl)pyridine-1-oxide 
• 13723-21-2 4,4'-dihydroxy-3,3'-(4-methoxy-phenylmethanediyl)-bis-thiochromen-2-one 
• 101974-75-8 2-[(4-Hydroxy-2-oxo-2H-thiochromen-3-yl)-(3-nitro-phenyl)-methyl]-indan-1,3-dione 
• 104960-48-7 2-[(4-Hydroxy-2-oxo-2H-thiochromen-3-yl)-(4-nitro-phenyl)-methyl]-indan-1,3-dione 
• 101974-74-7 2-[(4-Hydroxy-2-oxo-2H-thiochromen-3-yl)-(2-methoxy-phenyl)-methyl]-indan-1,3-dione 
• 104960-42-1 2-[(2-Chloro-phenyl)-(4-hydroxy-2-oxo-2H-thiochromen-3-yl)-methyl]-indan-1,3-dione 
• 104960-43-2 2-[(3-Chloro-phenyl)-(4-hydroxy-2-oxo-2H-thiochromen-3-yl)-methyl]-indan-1,3-dione 
• 104960-45-4 2-[(2,4-Dichloro-phenyl)-(4-hydroxy-2-oxo-2H-thiochromen-3-yl)-methyl]-indan-1,3-dione 
• 104960-41-0 2-[(4-Hydroxy-2-oxo-2H-thiochromen-3-yl)-(4-methoxy-phenyl)-methyl]-indan-1,3-dione 
• 104960-47-6 2-[(4-Bromo-phenyl)-(4-hydroxy-2-oxo-2H-thiochromen-3-yl)-methyl]-indan-1,3-dione 
• 104960-40-9 2-[(4-Hydroxy-2-oxo-2H-thiochromen-3-yl)-p-tolyl-methyl]-indan-1,3-dione 
• 104960-44-3 2-[(4-Chloro-phenyl)-(4-hydroxy-2-oxo-2H-thiochromen-3-yl)-methyl]-indan-1,3-dione 

Relevant articles and documents

Design, synthesis, and anticonvulsant evaluation of 4-GABA-3-nitrocoumarines, 1-thiocoumarines, quinolone-2-ones, and their derivatives

The novel group of 4-GABA-3-nitrocoumarines, 1-thiocoumarines, quinolone-2-ones, and their derivatives was designed as potential anticonvulsants using GABA pharmacophore and corresponding heterocyclic moieties. A number of compounds of this group were synthesized and studied in the maximum electroshock seizure (MES) test and in the model of primary-generalized convulsions caused by subcutaneous pentylenetetrazole (scPTZ) in mice. The most active compound in the MES test was found to be 1a (N-(3-nitrocoumarin-4-yl)-4-aminobutyric acid) at a dose range of 60–80 mg/kg that increased the number of survived animals up to 60% in comparison with the control group, whose survival rate was 10%. Compounds 1d (N-(3,6-dinitrocoumarin-4-yl)-4-amino-butyric acid methyl ester) at doses of 10–40 mg/kg and 3a (N-(3-nitro-2-oxo-1,2-dihydroquinolin-4-yl)-4-amino-butyric acid methyl ester) at a dose of 12.5 mg/kg had the most pronounced anticonvulsant effect in scPTZ test. [Figure not available: see fulltext.].

COUMARIN-BASED COMPOUNDS

Compounds including those of the Formula I where X, R1, R2 and subscript t are as defined herein, useful as γ-secretase inhibitors, are provided, as are compositions comprising the compounds, as well as methods for use of the compoun