p-Dimethylaminobenzalrhodanine

Base Information

• Chemical Name: p-Dimethylaminobenzalrhodanine
• CAS No.: 536-17-4
• Deprecated CAS: 41259-57-8,93522-26-0,664997-25-5,664997-25-5,93522-26-0
• Molecular Formula: C12H12N2OS2
• Molecular Weight: 264.372
• Hs Code.: 29349990
• European Community (EC) Number: 208-625-2
• UNII: 0SER53Q7RT
• DSSTox Substance ID: DTXSID7060207
• Wikidata: Q3599219
• ChEMBL ID: CHEMBL1736327
• Mol file: 536-17-4.mol

Synonyms:5-(4-(dimethylamino)benzylidene)rhodanine;DMABR

Chemical Property of p-Dimethylaminobenzalrhodanine

Chemical Property:

• Appearance/Colour: red fluffy powder
• Melting Point: 285-288 °C(lit.)
• Refractive Index: 1.703
• Boiling Point: 430 °C at 760 mmHg
• PKA: 8.17±0.30(Predicted)
• Flash Point: 213.8 °C
• PSA: 89.73000
• Density: 1.368 g/cm³
• LogP: 2.57020
• Storage Temp.: Store below +30°C.
• Solubility.: dioxane: soluble0.1g/10 mL (hot)
• Water Solubility.: Insoluble in water, 993.7(mg/L) at 25°C
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 264.03910536
• Heavy Atom Count: 17
• Complexity: 358

Purity/Quality:

98% ^*data from raw suppliers

4-Dimethylaminobenzylidenerhodanine >98.0%(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36/37-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Dyes -> Indicator Dyes
• Canonical SMILES: CN(C)C1=CC=C(C=C1)C=C2C(=O)NC(=S)S2
• Uses: As 0.03% solution in acetone for detection of silver, mercury, copper, gold, platinum and palladium ions. Applied for the detection of Ag, Au, Cu, Hg, Pd, Pt, alkaloids, antipyrin, indican, sulfonamide, urobilinogen. Reagent for the determination of silver, palladium, mercury and gold. Also used in the photometric determination of auto radiograms. 5-(4-Dimethylaminobenzylidene)rhodanine is a silver-specific dye that is used to quantitate the autoradiographic deposition of silver onto X-ray film in a colorimetric assay. 5-(4-Dimethylaminobenzylidene)rhodanine is used as an indicator in the titration of cyanide solution with silver nitrate solution.

Technology Process of p-Dimethylaminobenzalrhodanine

There total 4 articles about p-Dimethylaminobenzalrhodanine 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: 96.0%

2-thioxo-4-thiazolidinone (141-84-4) + 4-dimethylamino-benzaldehyde (100-10-7) → 5-(4-dimethylaminobenzylidene)rhodanine (536-17-4)

Guidance literature:

With thiourea; urea; at 110 ℃; for 0.0833333h; Neat (no solvent);

DOI:10.1016/j.bmcl.2012.07.049

Reference yield:

C12H11N2OS2(1-)*Na(1+) → 5-(4-dimethylaminobenzylidene)rhodanine (536-17-4)

Guidance literature:

Multi-step reaction with 2 steps

1: H⁺ / H₂O

With hydrogen cation; In water;

DOI:10.1023/A:1015514217370

Reference yield:

3-Benzoyl-5-[1-(4-dimethylamino-phenyl)-meth-(Z)-ylidene]-2-thioxo-thiazolidin-4-one → 5-(4-dimethylaminobenzylidene)rhodanine (536-17-4) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

With hydrogen cation; In water;

DOI:10.1023/A:1015514217370

upstream raw materials:

2-thioxo-4-thiazolidinone

4-dimethylamino-benzaldehyde

N,N-dimethyl-4-((phenylimino)methyl)aniline

Downstream raw materials:

5-(4'-dimethylamino-phenylmethylene)-2-(ethylthio)-1,3-thiazol-4-one

3-{[bis-(2-chloro-ethyl)-amino]-methyl}-5-(4-dimethylamino-benzylidene)-2-thioxo-thiazolidin-4-one

5-(4-dimethylamino-benzylidene)-thiazolidine-2,4-dithione

5-(4-dimethylamino-benzylidene)-3-(tetra-O-acetyl-β-D-glucopyranosyl)-2-thioxo-thiazolidin-4-one

Refernces

• 1、 Sun, Zhi-Gang,Xu, Yun-Jie,Xu, Jian-Fei,Liu, Qi-Xing,Yang, Yu-Shun,Zhu, Hai-Liang. "Introducing broadened antibacterial activity to rhodanine derivatives targeting enoyl-acyl carrier protein reductase". . p. 125 - 129. Retrieved 2019/03/28.
• 2、 Khazaei, Ardeshir,Veisi, Hojat,Safaei, Maryam,Ahmadian, Hossein. "Green synthesis of 5 arylidene-2,4-thiazolidinedione, 5-benzylidene rhodanine and dihydrothiophene derivatives catalyzed by hydrated ionic liquid tetrabutylammonium hydroxide in aqueous medium". . p. 270 - 278. Retrieved 2014/04/03.