Rhodanine

Base Information

• Chemical Name: Rhodanine
• CAS No.: 141-84-4
• Deprecated CAS: 38895-62-4
• Molecular Formula: C3H3NOS2
• Molecular Weight: 133.195
• Hs Code.: 29341000
• European Community (EC) Number: 205-505-1
• NSC Number: 1899
• UNII: 7O50LKL2G8
• DSSTox Substance ID: DTXSID4026002
• Nikkaji Number: J5.808D
• Wikipedia: Rhodanine
• Wikidata: Q2741084
• Metabolomics Workbench ID: 70041
• ChEMBL ID: CHEMBL224633
• Mol file: 141-84-4.mol

Synonyms:Rhodanine

Chemical Property of Rhodanine

Chemical Property:

• Appearance/Colour: light yellow to beige fine crystalline powder
• Vapor Pressure: 0.128mmHg at 25°C
• Melting Point: 165-169 °C(lit.)
• Refractive Index: 1.711
• Boiling Point: 218.2 °C at 760 mmHg
• PKA: pK (25°) 5.52
• Flash Point: 85.7 °C
• PSA: 86.49000
• Density: 1.59 g/cm³
• LogP: 0.46310
• Storage Temp.: -20°C
• Solubility.: methanol: soluble0.5g/10 mL, clear, colorless to greenish-yellow
• Water Solubility.: SOLUBLE IN HOT WATER
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 132.96560607
• Heavy Atom Count: 7
• Complexity: 122

Purity/Quality:

99.9% ^*data from raw suppliers

Rhodanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 22-26-39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Other Organic Compounds
• Canonical SMILES: C1C(=O)NC(=S)S1
• Uses: thiadiazole pharmaceutical intermediate In the synthesis of phenylalanine. In the case of reagents containing several potential donor atoms, one of the first steps in the study of complex formation is the specification of the functional groups which actually participate in the complexation reaction. The literature on rhodanine derivatives provides a good example of such examinations.

Technology Process of Rhodanine

There total 30 articles about Rhodanine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

carbon disulfide (75-15-0,12122-00-8) + sodium monochloroacetic acid (3926-62-3) → 2-thioxo-4-thiazolidinone (141-84-4)

Guidance literature:

carbon disulfide; With ammonium hydroxide; In water; at 40 ℃; for 0.5h;

sodium monochloroacetic acid; In water; for 0.416667 - 0.583333h;

With hydrogenchloride; In water; at 100 - 110 ℃;

DOI:10.1007/s11243-017-0159-3

Reference yield: 83.0%

rhodanine 3-acetic acid (5718-83-2) + isobutyraldehyde (78-84-2) → 2-thioxo-4-thiazolidinone (141-84-4) + 3-carboxymethyl-5-2,2-dimethylpropylidene

Guidance literature:

With hydrogenchloride; sodium acetate; acetic acid; In N,N-dimethyl-formamide;

Reference yield: 77.0%

mercaptoacetic acid (68-11-1) + thiourea (17356-08-0) → 2-thioxo-4-thiazolidinone (141-84-4)

Guidance literature:

With hydrogenchloride; In toluene; at 110 ℃; for 8h; Solvent; Reagent/catalyst; Temperature; Catalytic behavior;

DOI:10.1055/a-1485-5925

upstream raw materials:

diethyl 2-chloromalonate

ammonium dithiocarbamate

3-aminorhodanine

thiocyanic acid

Downstream raw materials:

5-((Z)-furfurylidene)-2-morpholino-thiazol-4-one

E-5-(2-hydroxyphenylmethylene)-2-morpholino-4-oxo-2-thiazoline

2-morpholino-5-vanillylidene-thiazol-4-one

5-pyrrol-2-ylmethylene-2-thioxo-thiazolidin-4-one

Refernces

• 1、 Dains,Krober. "-". . p. 1830. Retrieved 1939.
• 2、 Pan, Zhenliang,An, Wankai,Wu, Lulu,Fan, Liangxin,Yang, Guoyu,Xu, Cuilian. "A New Synthesis Strategy for Rhodanine and Its Derivatives". . p. 1131 - 1134. Retrieved 2021/05/25.
• 3、 Brahmbhatt, Harshad,Molnar, Maja,Pavi?, Valentina,Rastija, Vesna. "Synthesis, characterization, antibacterial and antioxidant potency of nsubstituted- 2-sulfanylidene-1,3-thiazolidin-4-one derivatives and QSAR study". . p. 840 - 849. Retrieved 2020/01/25.