2,4-Thiazolidinedione, 5-(2-thienylmethylene)-, (Z)-

Base Information

• Chemical Name: 2,4-Thiazolidinedione, 5-(2-thienylmethylene)-, (Z)-
• CAS No.: 139336-31-5
• Molecular Formula: C₈H₅NO₂S₂
• Molecular Weight: 211.265
• DSSTox Substance ID: DTXSID80394570
• Mol file: 139336-31-5.mol

Synonyms:2,4-Thiazolidinedione, 5-(2-thienylmethylene)-, (Z)-;5-(thiophen-2-ylmethylidene)-1,3-thiazolidine-2,4-dione;139336-31-5;WAY-351919;SCHEMBL1250019;DTXSID80394570;DOOLJLRRQAYVGK-UHFFFAOYSA-N;5-(2-thienylmethylene)-2,4-thiazolidinedione;5-(2-thienylmethylene)thiazolidine-2,4-dione;5-(thiophen-2-ylmethylene)thiazolidine-2,4-dione

Chemical Property of 2,4-Thiazolidinedione, 5-(2-thienylmethylene)-, (Z)-

Chemical Property:

• PSA: 103.20000
• LogP: 2.34790
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 210.97617075
• Heavy Atom Count: 13
• Complexity: 288

Purity/Quality:

5-(2-Thienylmethylene)-1,3-thiazolidine-2,4-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CSC(=C1)C=C2C(=O)NC(=O)S2

Technology Process of 2,4-Thiazolidinedione, 5-(2-thienylmethylene)-, (Z)-

There total 4 articles about 2,4-Thiazolidinedione, 5-(2-thienylmethylene)-, (Z)- 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: 94.0%

thiophene-2-carbaldehyde (98-03-3) + thiazoline-2,4-dione (2295-31-0) → 5-thiophen-2-ylmethylenethiazolidine-2,4-dione (139336-31-5)

Guidance literature:

With Fe₃O₄/SiO₂-NH₂/Cu(II); In ethanol; for 0.5h; Catalytic behavior; Reflux; Green chemistry;

DOI:10.1007/s11243-017-0159-3

Reference yield: 66.6%

piperidine (110-89-4) + thiophene-2-carbaldehyde (98-03-3) + thiazoline-2,4-dione (2295-31-0) → 5-thiophen-2-ylmethylenethiazolidine-2,4-dione (139336-31-5)

Guidance literature:

In ethanol;

Reference yield:

α-mercapto-β-(2-thienyl) acrylic acid (98778-43-9) + trichloroacetonitrile (545-06-2) → 5-thiophen-2-ylmethylenethiazolidine-2,4-dione (139336-31-5)

Guidance literature:

In acetic acid; for 2h; Reflux;

DOI:10.3998/ark.5550190.0012.a20

upstream raw materials:

thiophene-2-carbaldehyde

thiazoline-2,4-dione

piperidine

α-mercapto-β-(2-thienyl) acrylic acid

Downstream raw materials:

4-[((Z)-2,4-dioxo-5-((thiophen-2-yl)methylene)thiazolidin-3-yl)methyl]benzoic acid

3-thiophen-2-yl-2-thioxo-propionic acid

Refernces

• 1、 Meirelles, Luan V.,de Castro, Pedro P.,Passos, Saulo T. A.,Carvalho, Bernardo B. P. P.,Franco, Chris H. J.,Correa, José R.,Neto, Brenno A. D.,Amarante, Giovanni W.. "Diverse 3-Methylthio-4-Substituted Maleimides through a Novel Rearrangement Reaction: Synthesis and Selective Cell Imaging". . p. 2809 - 2820. Retrieved 2022/02/16.
• 2、 Akhavan, Malihe,Foroughifar, Naser,Pasdar, Hoda,Khajeh-Amiri, Alireza,Bekhradnia, Ahmadreza. "Copper(II)-complex functionalized magnetite nanoparticles: a highly efficient heterogeneous nanocatalyst for the synthesis of 5-arylidenthiazolidine-2,4-diones and 5-arylidene-2-thioxothiazolidin-4-one". . p. 543 - 552. Retrieved 2017/08/15.