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Rhodanine-3-acetic acid structure
Rhodanine-3-acetic acid structure

Rhodanine-3-acetic acid

Iupac Name:2-(4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)acetic acid
CAS No.: 5718-83-2
Molecular Weight:191.219
Modify Date.: 2022-11-29 06:43


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1. Names and Identifiers
1.1 Name
Rhodanine-3-acetic acid
1.2 Synonyms

(4-Oxo-2-thioxo-1,3-thiazolidin-3-yl)acetic acid (4-Oxo-2-thioxothiazolidin-3-yl)acetic acid 2-(4-Oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)acetic acid 2-(4-Oxo-2-thioxothiazolidin-3-yl)acetic acid 2-Thioxo-4-oxothiazolidine-3-acetic acid 2-Thioxo-4-thiazolidinone-3-acetic acid 3-(Carboxymethyl)rhodanine 3-Carboxymethyl-2-thioxo-4-thiazolidone 3-Rhodanineacetic acid 3-Thiazolidineacetic acid 3-Thiazolidineacetic acid, 4-oxo-2-thioxo- 4-Oxo-2-thioxo-3-thiazolidineacetic acid 4-Oxo-2-thioxothiazolidine-3-acetic acid EINECS 227-220-1 MFCD00005491 N-(2-thioxo-4-oxothiazolidin)essigsure N-(Carboxymethyl)rhodanine N-Carboxymethylrhodanine NSC 40450 Rhodanine acetic acid Rhodanine-3-ethanoic acid Rhodanine-N-acetic acid RHODANINE-N-ACETIC ACID FOR SYNTHESIS

1.3 CAS No.
1.4 CID
1.6 Molecular Formula
C5H5NO3S2 (isomer)
1.7 Inchi
1.8 InChkey
1.9 Canonical Smiles
1.10 Isomers Smiles
2. Properties
2.1 Density
2.1 Melting point
2.1 Boiling point
2.1 Refractive index
1.5480 (estimate)
2.1 Flash Point
2.1 Precise Quality
2.1 PSA
2.1 logP
2.1 Solubility
methanol: soluble25mg/mL, clear, yellow
2.2 Appearance
2.3 Storage
Ambient temperatures.
2.4 Chemical Properties
PALE YELLOW FINE CRYSTALINE POWDER Rhodanine-3-acetic acid Preparation Products And Raw materials Raw materials
2.5 pKa
2.6 Water Solubility
>28.7 [ug/mL]
2.7 Stability
Stable under normal temperatures and pressures.
2.8 StorageTemp
Store in a tightly closed container. Store in a cool, dry area away from incompatible substances.
3. Use and Manufacturing
3.1 Methods of Manufacturing
General procedure: Mixture of amine or amino acid (1 mol), sodium hydroxide (22 percent) and carbon disulfide (1 mol) in 3 ml water was reacted in a microwave reactor (CEM Discover, Benchmate, USA) for 5 min at 100 °C at 80 W. After automatedcooling to 40 °C, sodium chloroacetate (1 mol) was addedand the mixture was reacted again at 100 °C for 5 min.After cooling (40 °C), conc. HCl (3 ml) was added and thereaction was completed at 110 C for 20–30 min. Thecrude product was extracted with ethyl acetate and purified(Nitsche and Klein, 2012).2-(4-Oxo-2-thioxothiazolidin-3-yl)acetic acid (2a) Yield;82.5 percent; mp 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); Anal.calcd.for C5H5NO3S2: C, 31.40; H, 2.64; N, 7.32. Found: C, 31.55; H, 2.53; N, 7.22.General Procedure for the Synthesis of Λ/-substituted Rhodanines (7a-f) To a solution of the requisite natural amino acid (typically 5 g, 30 mmol) in water (100 mL) was added NaOH (2.4 g, 2 eq) and CSGeneral procedure: A suspension of amine (5 mmol) and bis(carboxymethyl)trithiocarbonate (5.5 mmol) in water was reacted in a microwave reactor (Monowave 300, Anton Paar) at the different described time and temperature conditions. After automated cooling to 40°C the crude product was extracted with ethyl acetate and purified by flash chromatography (cyclohexane/ethyl acetate) using a Biotage Isolera One system.#10;#10;(b) Preparation of(4~oxo-2-thioxo-l, 3-thiazolidin-3-yl)acetic acid [II]In 250 ml cap. three necked round bottom flask equipped with stirrer, thermometer condenser, and oil bath , Methyl(4-oxo-2-thioxo-l, 3-thiazolidin-3-yl)acetate (28g, 0.1364mol) is stirred Example-5(a) ; Preparation of (4-oxo-2-thioxo~l , 3-thiazolidin-3-yl)acetic acid [II]In 100 ml three necked round bottom flask equipped with stirrer, condenser, thermometer, oil bath, Methyl(4-oxo-2-thioxo-l, 3-thiazolidin-3-yl)acetate (8g, 0.038mol) is stirred with mixture of 25ml acetic acid and 20ml of 25percent sulfuric acid solution at reflux temperature for 2 hours. 20ml 33percent aqueous acetic acid solution is added in the reaction mass. Reflux is maintained for 21 hours. The absence of methyl(4-oxo-2-thioxo-l, 3-thiazolidin~3-yl)acetate is checked by TLC. The reaction mass is dumped into cooled water. Aqueous layer is extracted with ethyl acetate, ethyl acetate layer is distilled out and triturated with 20ml hexane to give (4-oxo-2-thioxo-l, 3-thiazolidin-3-yl)acetic acid [II] as yellow colored product. Yield = 4gm (percentYield= 53.7percent)c) Preparation of
4. Safety and Handling
4.1 Hazard Codes
4.1 Risk Statements
4.1 Safety Statements
4.1 Hazard Declaration
4.1 Caution Statement
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
4.1 WGK Germany
4.1 Safety

Hazard Codes: IrritantXi
Risk Statements: 36/37/38-41
R36/37/38:Irritating to eyes, respiratory system and skin. 
R41:Risk of serious damage to the eyes.
Safety Statements: 26-36-39-25
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
HS Code: 29341000

4.2 Specification

  3-Thiazolidineaceticacid, 4-oxo-2-thioxo- , its cas register number is 5718-83-2. It also can be called 3-(Carboxymethyl)rhodanine ; 3-Rhodanineacetic acid ; 4-Oxo-2-thioxo-3-thiazolidineacetic acid ; EINECS 227-220-1 ; N-(Carboxymethyl)rhodanine ; NSC 40450 ; Rhodanine-N-acetic acid . 3-Thiazolidineaceticacid, 4-oxo-2-thioxo- (CAS NO.5718-83-2) is irritating to eyes, respiratory system and skin. And it's risk of serious damage to the eyes.


2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Signal word


Hazard statement(s)

H315 Causes skin irritation

H319 Causes serious eye irritation

H335 May cause respiratory irritation

Precautionary statement(s)

P264 Wash ... thoroughly after handling.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P261 Avoid breathing dust/fume/gas/mist/vapours/spray.

P271 Use only outdoors or in a well-ventilated area.


P302+P352 IF ON SKIN: Wash with plenty of water/...

P321 Specific treatment (see ... on this label).

P332+P313 If skin irritation occurs: Get medical advice/attention.

P362+P364 Take off contaminated clothing and wash it before reuse.

P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

P337+P313 If eye irritation persists: Get medical advice/attention.

P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.

P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.


P403+P233 Store in a well-ventilated place. Keep container tightly closed.

P405 Store locked up.


P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification


9. Other Information
9.0 Manufacturing Info
3-Thiazolidineacetic acid, 4-oxo-2-thioxo-: ACTIVE
10. Computational chemical data
  • Molecular Weight: 191.219g/mol
  • Molecular Formula: C5H5NO3S2
  • Compound Is Canonicalized: True
  • XLogP3-AA: 0.4
  • Exact Mass: 190.97108537
  • Monoisotopic Mass: 190.97108537
  • Complexity: 228
  • Rotatable Bond Count: 2
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 5
  • Topological Polar Surface Area: 115
  • Heavy Atom Count: 11
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
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