Rhodanine-3-acetic acid Chemical Properties

Melting point:

145-148 °C (lit.)

Boiling point:

375.4±44.0 °C(Predicted)

Density 

1.492 (estimate)

refractive index 

1.5480 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

methanol: soluble25mg/mL, clear, yellow

form 

solid

pka

3.75±0.10(Predicted)

color 

Off-White to Pale Beige

BRN 

149513

InChI

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

InChIKey

JGRMXPSUZIYDRR-UHFFFAOYSA-N

SMILES

S1CC(=O)N(CC(O)=O)C1=S

CAS DataBase Reference

5718-83-2(CAS DataBase Reference)

EPA Substance Registry System

3-Thiazolidineacetic acid, 4-oxo-2-thioxo- (5718-83-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-41

Safety Statements 

26-36-39-25

WGK Germany 

3

F 

10-23

TSCA 

Yes

HS Code 

29341000

MSDS

• Language:English Provider:4-Oxo-2-thioxo-3-thiazolidinylacetic acid
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Rhodanine-3-acetic acid Usage And Synthesis

Chemical Properties

PALE YELLOW FINE CRYSTALINE POWDER

Uses

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

Synthesis

GENERAL METHOD: Glycine (1 mol), 22% sodium hydroxide solution and carbon disulfide (1 mol) were dissolved in 3 mL of water and placed in a microwave reactor (CEM Discover, Benchmate, USA) and reacted at 100°C for 5 min. After the reaction was completed, it was automatically cooled to 40 °C, sodium chloroacetate (1 mol) was added and the mixture was again reacted at 100 °C for 5 min. The reaction solution was cooled to 40 °C and concentrated. To the concentrate, 3 mL of hydrochloric acid was added and the reaction was continued at 110°C for 20-30 minutes. Upon completion of the reaction, the crude product was extracted with ethyl acetate and purified (refer to Nitsche and Klein, 2012 method). The product obtained was 2-(4-oxo-2-thioxothiazolidin-3-yl)acetic acid (2a) in 82.5% yield; melting point 245-247 °C; UV λmax 266, 215 nm; IR (KBr) νmax 3439, 1663, 1512, 1321, 896 cm-1; 1H NMR (DMSO-d6, 400 MHz): δ= 4.56 (2H, s, N-CH2), 4.41 (2H, s, H-5); 13C NMR (DMSO-d6, 100 MHz): δ= 202.80 (C=S, C-2), 173.72 (C=O, COOH), 167.29 (C=O, C-4), 44.77 (CH2, N-CH2), 35.94 ( CH2, C-5); elemental analysis (C5H5NO3S2) calculated values: C, 31.40; H, 2.64; N, 7.32. measured values: C, 31.55; H, 2.53; N, 7.22.

References

[1] Archiv der Pharmazie, 2012, vol. 345, # 1, p. 73 - 80
[2] Medicinal Chemistry Research, 2016, vol. 25, # 5, p. 994 - 1004
[3] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 4, p. 359 - 364
[4] Patent: WO2010/24783, 2010, A1. Location in patent: Page/Page column 79; 80
[5] Archives of Pharmacal Research, 2014, vol. 37, # 7, p. 852 - 861

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