5718-83-2

Basic information

• Product Name: Rhodanine-3-acetic acid
• Synonyms: 3-Thiazolidineacetic acid;Rhodanine acetic acid;Rhodanine-3-ethanoic acid;2-Thioxo-4-oxothiazolidine-3-acetic acid;Rhodanine-N-acetic acid,98%;RHODANINE-N-ACETIC ACID FOR SYNTHESIS;2-(4-Oxo-2-thioxothiazolidin-3-yl)acetic acid;TIMTEC-BB SBB003632
• CAS NO: 5718-83-2
• Molecular Formula: C₅H₅NO₃S₂
• Molecular Weight: 191.23
• EINECS: 227-220-1
• Product Categories: INTERMEDIATES;Heterocycles;Acetics acid and esters
• Mol File: 5718-83-2.mol
• Article Data: 30

Chemical Properties

• Melting Point: 145-148 °C(lit.)
• Boiling Point: 375.4 °C at 760 mmHg
• Flash Point: 180.8 °C
• Appearance: /solid
• Density: 1.492 (estimate)
• Vapor Pressure: 1.14E-06mmHg at 25°C
• Refractive Index: 1.5480 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: methanol: soluble25mg/mL, clear, yellow
• PKA: 3.75±0.10(Predicted)
• BRN: 149513
• CAS DataBase Reference: Rhodanine-3-acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Rhodanine-3-acetic acid(5718-83-2)
• EPA Substance Registry System: Rhodanine-3-acetic acid(5718-83-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-41
• Safety Statements: 26-36-39-25
• WGK Germany: 3
• F: 10-23
• TSCA: Yes
• Hazardous Substances Data: 5718-83-2(Hazardous Substances Data)

Usage

Chemical Properties

PALE YELLOW FINE CRYSTALINE POWDER

Uses

3-Rhodanineacetic Acid is an inhibitor for copper corrosion in acidic media.

InChI:InChI=1/C5H5NO3S2/c7-3-2-11-5(10)6(3)1-4(8)9/h1-2H2,(H,8,9)/p-1

Upstream product

• 3926-62-3 sodium monochloroacetic acid 
• 56-40-6 glycine 
• 105-39-5 chloroacetic acid ethyl ester 
• 2365-48-2 Methyl thioglycolate 
• 4385-41-5 isothiocyanato-acetic acid 
• 149789-77-5 methyl (4-oxo-2-thioxo-1,3-thiazolidine-3-yl)acetate 
• 75-15-0 carbon disulfide 
• 6861-95-6 N-dithiocarboxy-glycine ; ammonium salt 
• 6326-83-6 bis(carboxymethyl)trithiocarbonate 
• 79-11-8 chloroacetic acid 
• 39680-96-1 C₃H₅NO₂S₂*H₃N 
• 623-51-8 ethyl 2-sulfanylacetate 
• 29677-65-4 N-carboxymethylsulfanylthiocarbonyl-glycine 
• 141-84-4 2-thioxo-4-thiazolidinone 

Downstream Products

• 82158-77-8 (5-trans-cinnamyliden-4-oxo-2-thioxo-thiazolidin-3-yl)-acetic acid 
• 25651-76-7 {5-[1-methyl-2-(3-methyl-thiazolidin-2-yliden)-ethyliden]-4-oxo-2-thioxo-thiazolidin-3-yl}-acetic acid 
• 76971-10-3 {5-[(1-ethyl-1H-[2]quinolyliden)-ethyliden]-4-oxo-2-thioxo-thiazolidin-3-yl}-acetic acid 
• 25962-03-2 {5-[2-(3-ethyl-3H-benzothiazol-2-ylidene)-ethylidene]-4-oxo-2-thioxo-thiazolidin-3-yl}-acetic acid 
• 82158-61-0 3-Carboxymethyl-5--rhodanin 
• 82158-60-9 3-Carboxymethyl-5--rhodanin 
• 82158-64-3 3-Carboxymethyl-5-(indolyl-(3)-methylen)-rhodanin 
• 92423-68-2 3-Carboxymethyl-5-(5-brom-indolyl-(3)-methylen)-rhodanin 
• 92695-46-0 [5-(3-iodo-benzylidene)-4-oxo-2-thioxo-thiazolidin-3-yl]-acetic acid 
• 107518-74-1 [5-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylmethylene)-4-oxo-2-thioxo-thiazolidin-3-yl]-acetic acid 
• 91330-21-1 3-Carboxymethyl-5-(2-iodbenzyliden)rhodanin 
• 92695-47-1 [5-(4-iodo-benzylidene)-4-oxo-2-thioxo-thiazolidin-3-yl]-acetic acid 
• 1022-55-5 3-Carboxymethyl-5-(3'-isoxazolylmethylen)-rhodanin 
• 130786-47-9 {5-[4-Chloro-but-(Z)-ylidene]-4-oxo-2-thioxo-thiazolidin-3-yl}-acetic acid 

Relevant articles and documents

Design and synthesis of amino acid derivatives of substituted benzimidazoles and pyrazoles as Sirt1 inhibitors

Owing to its presence in several biological processes, Sirt1 acts as a potential therapeutic target for many diseases. Here, we report the structure-based designing and synthesis of two distinct series of novel Sirt1 inhibitors, benzimidazole mono-peptide

Pyrimidine-thiazolidinone derivatives

Pyrimidine-thiazolidinone derivatives may be used for preventing or treating diseases in humans or animals, and have demonstrated efficacy specifically in treating type-2 diabetes. Methods of synthesizing the pyrimidine-thiazolidinone derivatives, described herein, can provide high yields in a short time and with high purity. The pyrimidine-thiazolidinone derivatives demonstrate improved hypoglycemic activity compared to most anti-diabetic drugs currently available.

Highly efficient microwave synthesis of rhodanine and 2-thiohydantoin derivatives and determination of relationships between their chemical structures and antibacterial activity

Here we report studies on the synthesis of 12 new heterocyclic derivatives that differ in three structural motifs and the simultaneous evaluation of the impact of these three variables on the biological properties. The examined compounds are based on rhodanine and 2-thiohydantoin cores equipped with hydrogen or carboxymethyl substituents at the N-3 position and linked to a triphenylamine moiety through 1,4-phenylene, 1,4-naphthalenylene and 1,9-anthracenylene spacers at the C-5 position of the heterocycles. All the compounds were synthesized very quickly, selectively and in high yields according to the developed microwave-assisted Knoevenagel condensation protocol, and they were characterized thoroughly with NMR, FT-IR and ESI-HRMS techniques. The derivatives were tested for their activity against selected strains of Gram-positive and Gram-negative bacteria and yeast. Two compounds showed good activity against Gram-positive bacteria, and all of them showed low cytotoxicity against three cell lines of the human immune system. Based on membrane permeability assays it was demonstrated that the active compounds do not penetrate the cell membrane, and thus they must act on the bacterial cell surface. Finally, we proved that the evaluated structure modifications had a synergistic effect and the simultaneous presence of a 1,4-phenylene spacer and carboxymethyl group at N-3 caused the highest boost in antimicrobial activity.