| Identification | More | [Name]
Rhodanine-3-acetic acid | [CAS]
5718-83-2 | [Synonyms]
2-THIOXO-4-THIAZOLIDINONE-N-ACETIC ACID
(4-OXO-2-THIOXO-1,3-THIAZOLIDIN-3-YL)ACETIC ACID
4-OXO-2-THIOXO-3-THIAZOLIDINEACETIC ACID
4-OXO-2-THIOXO-3-THIAZOLIDINYLACETIC ACID
(4-OXO-2-THIOXO-THIAZOLIDIN-3-YL)ACETIC ACID
AKOS B023269
AKOS BBS-00002149
AURORA 4784
CARBOXYMETHYL RHODANINE
IFLAB-BB F1074-0188
N-CARBOXYMETHYLRHODANINE
OTAVA-BB BB0123270317
RHODANINE-3-ACETIC ACID
RHODANINE-N-ACETIC ACID
TIMTEC-BB SBB003632
3-CarboxmethylRhadanine
4-oxo-2-thioxo-3-thiazolidineaceticaci
N-(2-thioxo-4-oxothiazolidine)aceticacid
2-Thioxo-4-thiazolidinone-3-acetic acid
3-Carboxymethyl Rhodanine | [EINECS(EC#)]
227-220-1 | [Molecular Formula]
C5H5NO3S2 | [MDL Number]
MFCD00005491 | [Molecular Weight]
191.23 | [MOL File]
5718-83-2.mol |
| Chemical Properties | Back Directory | [Appearance]
PALE YELLOW FINE CRYSTALINE POWDER | [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]
5718-83-2(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R41:Risk of serious damage to eyes. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S39:Wear eye/face protection .
S25:Avoid contact with eyes . | [WGK Germany ]
3
| [F ]
10-23 | [TSCA ]
Yes | [HS Code ]
29341000 |
| Hazard Information | Back Directory | [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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