Thiocoumarin

Base Information

• Chemical Name: Thiocoumarin
• CAS No.: 3986-98-9
• Molecular Formula: C9H6OS
• Molecular Weight: 162.212
• UNII: CM773J3THB
• Wikidata: Q27093456
• Metabolomics Workbench ID: 147046
• Mol file: 3986-98-9.mol

Synonyms:THIOCOUMARIN;CM773J3THB;SCHEMBL929244;DB02462;FC1;4-[3-(dimethylamino)propoxy]-2H-thiochromen-2-one;Q27093456

Chemical Property of Thiocoumarin

Chemical Property:

• Vapor Pressure: 0.034mmHg at 25°C
• Melting Point: 97 °C
• Boiling Point: 250.6°Cat760mmHg
• Flash Point: 105.3°C
• PSA: 45.23000
• Density: 1.29g/cm³
• LogP: 3.16230
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 263.09799996
• Heavy Atom Count: 18
• Complexity: 328

Purity/Quality:

97% ^*data from raw suppliers

2H-1-BENZOPYRAN-2-THIONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CCCOC1=CC(=O)SC2=CC=CC=C21
• General Description: 2H-1-Benzopyran-2-thione, also known as 2-thiocoumarin, is a sulfur-containing analog of coumarin where the carbonyl oxygen is replaced by a sulfur atom. It can be synthesized through the thionation of coumarin derivatives using reagents like Lawesson's or Davy's reagent, as demonstrated in the preparation of tert-butyl substituted thiocoumarins. 2H-1-Benzopyran-2-thione is of interest in studies involving radical anions and spectroscopic investigations, such as EPR spectra analysis. Its structural confirmation is typically achieved via NMR spectroscopy and X-ray crystallography.

Technology Process of Thiocoumarin

There total 9 articles about Thiocoumarin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

coumarin (91-64-5) → 2-thiocoumarin (3986-98-9)

Guidance literature:

With tetraphosphorus decasulfide; In 5,5-dimethyl-1,3-cyclohexadiene; for 12h; Inert atmosphere; Reflux;

DOI:10.1016/j.tet.2010.05.100

Reference yield: 63.0%

benzothiaferrole (12086-84-9) → 2-thiocoumarin (3986-98-9) + iron (7439-89-6) + Benzo[b]thiophene (95-15-8,11095-43-5)

Guidance literature:

flash vac. pyrolysis in a Pyrex tube connected with a cold trap (E-5 Torr, 285-315°C); coating of the hot zone by Fe, rinsing of trap with acetone, GC;

DOI:10.1021/om00095a024

Reference yield: 60.0%

→ 2-thiocoumarin (3986-98-9)

Guidance literature:

upstream raw materials:

o-Coumaric acid

coumarin

o-Allylphenol

3,4-dihydro-2H-[1]benzopyran-2-thione

Downstream raw materials:

coumarin-phenylhydrazone

o-hydroxycinnamic acid thiopiperidide

triphenyl arsine sulfide

2-[1-(4-Chloro-phenyl)-meth-(Z)-ylidene]-2H-chromene

Refernces

Preparation of new tert-butyl substituted coumarins, thiocoumarins and dithiocoumarins

10.1080/10426500701340949

The research focuses on the preparation of new tert-butyl substituted coumarins, thiocoumarins, and dithiocoumarins. The study was motivated by the researchers' interest in these compounds for their investigations on the EPR spectra of ester, thioester, and dithiopyrone radical anions. The researchers synthesized various compounds, starting from tert-butylphenols and diketene to prepare 6-tert-butyl-4-methylcoumarin and 6,8-di-tert-butyl-4-methylcoumarin via aryl acetoacetates. Thionation of these coumarins with Lawesson's or Davy's reagent led to the formation of the corresponding thion- and dithiocoumarins. Key chemicals involved in the research include 4-tert-butylphenol, 2,4-di-tert-butylphenol, 4-tert-butylthiophenol, diketene, sulfuric acid, aluminum trichloride, and various reagents for thionation such as Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 1,3-disulfide) and Davy's reagent (2,4-bis(methylthio)-1,3,2,4-dithiadiphosphetane 2,4-disulfide). The structures of the synthesized compounds were confirmed using NMR spectroscopy and X-ray structure analysis.