3D Mol Similar

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

Introduction:

PALE YELLOW FINE CRYSTALINE POWDER

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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.: 5718-83-2

1.4 CID: 79793

1.5 EINECS(EC#): 227-220-1

1.6 Molecular Formula: C5H5NO3S2 (isomer)

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

1.8 InChkey: JGRMXPSUZIYDRR-UHFFFAOYSA-N

1.9 Canonical Smiles: C1C(=O)N(C(=S)S1)CC(=O)O

1.10 Isomers Smiles: C1C(=O)N(C(=S)S1)CC(=O)O

2. Properties

2.1 Density: 1.72

2.1 Melting point: 144-148℃

2.1 Boiling point: 375.4°Cat760mmHg

2.1 Refractive index: 1.5480 (estimate)

2.1 Flash Point: 180.8°C

2.1 Precise Quality: 190.97100

2.1 PSA: 115.00000

2.1 logP: -0.13080

2.1 Solubility: methanol: soluble25mg/mL, clear, yellow

2.2 Appearance: PALE YELLOW FINE CRYSTALINE POWDER

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: 3.75±0.10(Predicted)

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: Xi

4.1 Risk Statements: R41

4.1 Safety Statements: S25;S39

4.1 Hazard Declaration: H315

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: 3

4.1 Safety: Hazard Codes: Xi
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.

5. MSDS

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

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	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.
Response	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.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

7. Synthesis Route

5718-83-2Total: 7 Synthesis Route

105-39-5 84 Suppliers

5718-83-2 120 Suppliers

Literatures:
Monatshefte fuer Chemie, , vol. 29, p. 402 Chemische Berichte, , vol. 41, p. 1901
Yield: null

6326-83-6 23 Suppliers

56-40-6 928 Suppliers

5718-83-2 120 Suppliers

Literatures:
Nitsche, Christoph; Klein, Christian D. Tetrahedron Letters, 2012 , vol. 53, # 39 p. 5197 - 5201
Yield: ~5%

3926-62-3 98 Suppliers

56-40-6 928 Suppliers

5718-83-2 120 Suppliers

Literatures:
Yakugaku Zasshi, , vol. 79, p. 1462,1464, 1465 Chem.Abstr., , p. 6689
Yield: null

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8. Precursor and Product

precursor:

3926-62-3

6861-95-6

105-39-5

56-40-6

4385-41-5

2365-48-2

6326-83-6

75-15-0

product :

82158-64-3

82158-61-0

82159-06-6

92695-47-1

82158-60-9

1022-55-5

107518-74-1

29947-11-3

25651-76-7

25962-03-2

125261-87-2

91330-21-1

92423-68-2

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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
CACTVS Substructure Key Fingerprint: AAADcYBiMABgAAAAAAAAAAAAAAAAAWAAAAAAAAAAAAAAAAAAAAAAHgQACAAAAADFwASACAMAAggMAAGQGAAAAABAABgAAACIAAACAAAAACAAAAAABgCQAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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CAS 5718-83-2 Rhodanine-3-Acetic Acid / 3-Thiazolidineacetic Acid / Rhodanine Acetic Acid / Rhodanine-3-Ethanoic Acid