51226-17-6

Basic information

• Product Name: (2,4-DIOXO-1,3-THIAZOLIDIN-5-YL)ACETYL CHLORIDE
• Synonyms: TIMTEC-BB SBB009657;ART-CHEM-BB B023341;ASINEX-REAG BAS 10149029;(2,4-DIOXO-1,3-THIAZOLIDIN-5-YL)ACETYL CHLORIDE;(2,4-DIOXO-THIAZOLIDIN-5-YL)-ACETYL CHLORIDE;AKOS BBS-00002218
• CAS NO: 51226-17-6
• Molecular Formula: C₅H₄ClNO₃S
• Molecular Weight: 193.61
• Mol File: 51226-17-6.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2,4-DIOXO-1,3-THIAZOLIDIN-5-YL)ACETYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (2,4-DIOXO-1,3-THIAZOLIDIN-5-YL)ACETYL CHLORIDE(51226-17-6)
• EPA Substance Registry System: (2,4-DIOXO-1,3-THIAZOLIDIN-5-YL)ACETYL CHLORIDE(51226-17-6)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• HazardClass: IRRITANT
• Hazardous Substances Data: 51226-17-6(Hazardous Substances Data)

Usage

Description

(2,4-DIOXO-1,3-THIAZOLIDIN-5-YL)ACETYL CHLORIDE is a chemical compound with the molecular formula C6H6ClNO3S. It is a derivative of thiazolidine, which is a five-membered heterocyclic compound containing a sulfur and nitrogen atom. (2,4-DIOXO-1,3-THIAZOLIDIN-5-YL)ACETYL CHLORIDE is commonly used as a reagent in organic synthesis for the preparation of various chemical compounds. As an acetylating agent, it is used to introduce an acetyl group into organic molecules, making it a versatile compound in the field of chemistry and chemical production.

Uses

Used in Organic Synthesis:
(2,4-DIOXO-1,3-THIAZOLIDIN-5-YL)ACETYL CHLORIDE is used as a reagent for the preparation of various chemical compounds. Its ability to introduce an acetyl group into organic molecules makes it a valuable tool in the synthesis of a wide range of chemical products.
Used in Pharmaceutical Production:
In the pharmaceutical industry, (2,4-DIOXO-1,3-THIAZOLIDIN-5-YL)ACETYL CHLORIDE is used as an acetylating agent in the production of various pharmaceuticals. Its role in introducing acetyl groups into organic molecules is crucial for the synthesis of certain drugs.
Used in Agrochemical Production:
(2,4-DIOXO-1,3-THIAZOLIDIN-5-YL)ACETYL CHLORIDE also finds application in the agrochemical industry, where it is used as an acetylating agent in the synthesis of various agrochemicals. This contributes to the development of effective products for agricultural use.
Used in Chemical Research:
In the field of chemical research, (2,4-DIOXO-1,3-THIAZOLIDIN-5-YL)ACETYL CHLORIDE may have other applications, such as serving as a reagent in the study of chemical reactions and the development of new synthetic methods. Its versatility makes it a valuable compound for researchers exploring various aspects of chemistry.

Upstream product

• 875-97-8 2-(2,4-dioxothiazolidin-5-yl)acetic acid 

Downstream Products

• 1018166-66-9 1-[(2,4-dioxothiazolidin-5-yl)acetyl]-4-phenyl-5-thioxo-4,5-dihydro-1,2,4-triazole 
• 1140826-17-0 1-[(2,4-dioxothiazolidin-5-yl)acetyl]-5-oxo-4-phenyl-4,5-dihydro-1,2,4-triazole 
• 405925-28-2 N-(thiazol-2-yl)-2-(2,4-dioxothiazolidin-5-yl)acetamide 
• 308295-15-0 2-(2,4-dioxo-thiazolidin-5-yl)-N-(4-sulfamoyl-phenyl)-acetamide 
• 1293365-98-6 2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(5-(-3,4,5-trimethoxyphenyl)-1,3,4-thiadiazol-2-yl)acetamide 
• 1293365-97-5 2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(5-(-3,4-dimethoxyphenyl)-1,3,4-thiadiazol-2-yl)acetamide 
• 1293365-89-5 2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(5-phenyl-1,3,4-thiadiazol-2-yl)acetamide 
• 1293365-96-4 2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(5-4-methoxyphenyl-1,3,4-thiadiazol-2-yl)acetamide 
• 1293365-93-1 2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(5-2-chlorophenyl-1,3,4-thiadiazol-2-yl)acetamide 
• 1293366-00-3 2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(5-3-nitrophenyl-1,3,4-thiadiazol-2-yl)acetamide 
• 1293366-01-4 2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(5-4-nitrophenyl-1,3,4-thiadiazol-2-yl)acetamide 
• 1293365-99-7 2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(5-2-nitrophenyl-1,3,4-thiadiazol-2-yl)acetamide 
• 1293365-95-3 2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(5-3-methoxyphenyl-1,3,4-thiadiazol-2-yl)acetamide 
• 1293365-92-0 2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(5-4-fluorophenyl-1,3,4-thiadiazol-2-yl)acetamide 

Relevant articles and documents

Synthesis and in vitro antiproliferative and antibacterial activity of new thiazolidine-2,4-dione derivatives

In our present research, we synthesised new thiazolidine-2,4-diones (12–28). All the newly synthesised compounds were evaluated for antiproliferative and antibacterial activity. Antiproliferative evaluation was carried out using normal human skin fibroblasts and tumour cell lines: A549, HepG2, and MCF-7. The IC50 values were determined for tested compounds revealing antiproliferative activity. Moreover, safety index (SI) was calculated. Among all tested derivatives, the compound 18 revealed the highest antiproliferative activity against human lung, breast, and liver cancer cells. More importantly, the derivative 18 showed meaningfully lower IC50 values when compared to the reference substance, irinotecan, and relatively high SI values. Moreover, newly synthesised compounds were screened for the bacteria growth inhibition in vitro. According to our screening results, most active compound was the derivative 18 against Gram-positive bacteria. Therefore, it may be implied that the novel compound 18 appears to be a very promising agent for anticancer treatment.

Thiazole-bearing 4-thiazolidinones as new anticonvulsant agents

Here, we describe the synthesis and anticonvulsant activity of thiazole-bearing hybrids based on 2-imino-4-thiazolidinone and 2,4-dioxothiazolidine-5-carboxylic acid cores. The structure of target compounds was based on the following: (i) A combination of two thiazole cores; (ii) similarity to ralitolin’s structure; (iii) the compliance with structural requirements for the new anticonvulsants. Target compounds were synthesized via known approaches based on Knoenavegel reaction, alkylation reaction, and one-pot three-component reaction. Anticonvulsant properties of compounds were evaluated in two different models—pentylenetetrazole-induced seizures and maximal electroshock seizure tests. Among the tested compounds 5Z-(3-nitrobenzylidene)-2-(thiazol-2-ylimino)-thiazolidin-4-one Ib, 2-[2,4-dioxo-5-(thiazol-2-ylcarbamoylmethyl)-thiazolidin-3-yl]-N-(2-trifluoromethylphenyl)acetamide IId and (2,4-dioxo-5-(thiazol-2-ylcarbamoylmethylene)-thiazolidin-3-yl)acetic acid ethyl ester IIj showed excellent anticonvulsant activity in both models. The directions of compounds modification based on SAR aspects were discussed. The results of the study provide a basis for further study of the anticonvulsant properties of selected thiazole-thiazolidinones.

New thiazolidinedione-5-acetic acid amide derivatives: Synthesis, characterization and investigation of antimicrobial and cytotoxic properties

The present work describes the synthesis, antimicrobial and cytotoxic activity of 2,4-thiazolidinedione- 5-acetic acid amides 3a-n. The structures of the compounds were confirmed by IR, 1H, 13C NMR and elemental analysis. All compounds were tested for antimicrobial activity by twofold serial dilution technique. The preliminary results revealed that the compound 3d exhibits promising antibacterial and antifungal activity. The cytotoxic (MTT) activity of 2,4-thiazolidinedione-5-acetic acid amides were tested in four tumour cell lines. We found that compound 3j inhibited proliferation of HeLa, HT29, A549 and MCF-7 cell lines with IC50 values of 33, 35, 30 and 36 μM, respectively. Springer Science+Business Media, LLC 2011.