2,4-Thiazolidinedione

Base Information

• Chemical Name: 2,4-Thiazolidinedione
• CAS No.: 2295-31-0
• Molecular Formula: C3H3NO2S
• Molecular Weight: 117.128
• Hs Code.: 29341000
• European Community (EC) Number: 218-941-2
• NSC Number: 6745
• UNII: AA68LXK93C
• DSSTox Substance ID: DTXSID5040623
• Nikkaji Number: J48.702C
• Wikipedia: Thiazolidinedione
• Wikidata: Q1393556
• Metabolomics Workbench ID: 57586
• ChEMBL ID: CHEMBL85398
• Mol file: 2295-31-0.mol

Synonyms:2,4-thiazolidinedione;2,4-thiazolidinedione potassium;T-174;thiazolidinedione

Chemical Property of 2,4-Thiazolidinedione

Chemical Property:

• Appearance/Colour: White to off-white powder
• Vapor Pressure: 0.000809mmHg at 25°C
• Melting Point: 125-127 °C(lit.)
• Refractive Index: 1.577
• Boiling Point: 305.7 °C at 760 mmHg
• PKA: 6.50±0.10(Predicted)
• Flash Point: 138.7 °C
• PSA: 71.47000
• Density: 1.516 g/cm³
• LogP: 0.29820
• Storage Temp.: Store below +30°C.
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in water (30 mg/ml at 3°C), methanol, DMSO, ethanol, and ethyl ether.
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 116.98844951
• Heavy Atom Count: 7
• Complexity: 122

Purity/Quality:

99% ^*data from raw suppliers

2,4-Thiazolidinedione ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C(=O)NC(=O)S1
• Recent ClinicalTrials: A Study of Two Doses of Dulaglutide (LY2189265) in Japanese Patients With Type 2 Diabetes
• Uses: Inhibitor of enzyme 2,4-Thiazolidinedione may be used in the synthesis of sixteen 5-arylidene-2,4-thiazolidinediones, via ultrasound-promoted aldol condensation reaction. It may be used as starting material for the synthesis of drugs with antihyperglycemic activity.

Technology Process of 2,4-Thiazolidinedione

There total 70 articles about 2,4-Thiazolidinedione 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: 98.0%

4-[[2-methyl-1-oxo-1,2-dihydrophthalazin-4-yl]methoxy]benzaldehyde (214282-10-7) → thiazoline-2,4-dione (2295-31-0) + 5-[4-[[2-Methyl-1-oxo-1,2-dihydro-phthalazin-4-yl]methoxy]phenyl methylene]thiazolidin-2,4-dione (214281-86-4)

Guidance literature:

Reference yield: 94.0%

thiourea (17356-08-0) + chloroacetyl chloride (79-04-9) → thiazoline-2,4-dione (2295-31-0)

Guidance literature:

thiourea; chloroacetyl chloride; In water; for 0.333333h;

With hydrogenchloride; In water; for 7 - 8h; Reflux;

DOI:10.1007/s11243-017-0159-3

Reference yield: 91.0%

thiourea (17356-08-0) + chloroacetic acid (79-11-8) → thiazoline-2,4-dione (2295-31-0)

Guidance literature:

With hydrogenchloride; water; at 0 ℃; Reflux;

DOI:10.1080/14756366.2020.1715388

upstream raw materials:

2-thioxo-4-thiazolidinone

chloroacetic acid

2-phenylaminothiazol-4-one

α-thiocyanato-acetic acid amide

Downstream raw materials:

AS041164

(5Z)-5-(4-aminobenzylidene)-1,3-thiazolidine-2,4-dione

3-[5-(4-nitro-phenoxy)-pentyl]-thiazolidine-2,4-dione

5-cyclohexyLiDene-thiazolidine-2,4-dione

Refernces

• 1、 El-Adl, Khaled,Sakr, Helmy,Nasser, Mohamed,Alswah, Mohamed,Shoman, Fatma M. A.. "5-(4-Methoxybenzylidene)thiazolidine-2,4-dione-derived VEGFR-2 inhibitors: Design, synthesis, molecular docking, and anticancer evaluations". . . Retrieved 2020.
• 2、 Rodrigues, Maria do D.,Santiago, Priscila B.G.S.,Marques, Karla M.R.,Pereira, Valéria R.A.,de Castro, Maria C.A.B.,Cantalice, Jeanne C.L.L.,da Silva, Teresinha G.,Adam, M?nica L.,do Nascimento, Silene C.,de Albuquerque, Julianna F.C.,Militao, Gardenia C.G.. "Selective cytotoxic and genotoxic activities of 5-(2-bromo-5-methoxybenzylidene)-thiazolidine-2,4-dione against NCI-H292 human lung carcinoma cells". . p. 446 - 454. Retrieved 2018.
• 3、 Naik, Tangali R. Ravikumar,Naik, Halehatty S. Bhojya,Naik, Halehatty R. Prakash,Raghavendra,Ramesha. "Synthesis of novel 2-seleno-1,8-naphthyridines derivatives". . p. 1968 - 1974. Retrieved 2008.
• 4、 Hamama, Wafaa S.,Ismail, Mohamed A.,Soliman, Mamdouh S.,Shaaban, Saad,Zoorob, Hanafi H.. "Synthesis and characterization via molecular quantum parameters of 2H-thiazolo[3,2-a]pyrimidine-3,5,7(6H)-trione". . p. 494 - 498. Retrieved 2012.
• 5、 Levshin, I. B.,Chistyakov, V. V.,Pol'shakov, V. I.,Sheinker, Yu. N.. "2-ALLYLAMINOTHIAZOLIN-4-ONE IN ACYLATION REACTIONS". . p. 910 - 914. Retrieved 1987.
• 6、 Kavalek, Jaromir,Machacek, Vladimir,Sterba, Vojeslav. "COUPLING KINETICS OF 4-SULFOBENZENEDIAZONIUM ION WITH 2,4-THIAZOLIDINEDIONE, ITS 3-METHYL DERIVETIVE AND 3-METHYL-5-ISOXAZOLONE". . p. 2022 - 2028. Retrieved 1994.
• 7、 Meng, Ge,Li, Zhen-Yu,Zheng, Mei-Lin. "An efficient one-step method for the large-scale synthesis of 2,4-thiazolidinedione". . p. 572 - 574. Retrieved 2008.
• 8、 Levshin, I. B.,Grigor'eva, I. V.,Tsurkan, A. A.,Tarasyavichus, E. L.,V'yunov, K. A.,Ginak, A. I.. "INVESTIGATION OF THE REACTIVITIES AND TAUTOMERISM OF AZOLIDONES. 52. SYNTHESIS OF 2- AND 3-ALLYL-SUBSTITUTED PSEUDOTHIOHYDANTOINS". . p. 277 - 279. Retrieved 1985.
• 9、 Ghodsi, Shahram,Alipour, Eskandar,Amini, Mohsen,Miri, Ramin,Tagi-Ganji, Karim Masoud,Hosseini, Marjan,Mirkhani, Hossein,Shafiee, Abbas. "The synthesis and characterization of new asymmetrical dihydropyridine derivatives containing a 2,4-dichloro-5-thiazolyl substituent". . p. 2435 - 2444. Retrieved 2006.
• 10、 El-Adl, Khaled,El-Helby, Abdel-Ghany A.,Sakr, Helmy,Ayyad, Rezk R.,Mahdy, Hazem A.,Nasser, Mohamed,Abulkhair, Hamada S.,El-Hddad, Sanadelaslam S. A.. "Design, synthesis, molecular docking, anticancer evaluations, and in silico pharmacokinetic studies of novel 5-[(4-chloro/2,4-dichloro)benzylidene]thiazolidine-2,4-dione derivatives as VEGFR-2 inhibitors". . . Retrieved 2020/10/20.