Coumarin 6

Base Information

• Chemical Name: Coumarin 6
• CAS No.: 38215-36-0
• Deprecated CAS: 54576-82-8
• Molecular Formula: C20H18N2O2S
• Molecular Weight: 350.441
• Hs Code.: 29329990
• European Community (EC) Number: 253-830-2
• NSC Number: 290432
• UNII: 48DU8Q9UAU
• DSSTox Substance ID: DTXSID5068079
• Nikkaji Number: J294.613K
• Wikidata: Q27123017
• ChEMBL ID: CHEMBL212037
• Mol file: 38215-36-0.mol

Synonyms:Coumarin,3-(2-benzothiazolyl)-7-(diethylamino)- (6CI,7CI);3-(2-Benzothiazolyl-7-(diethylamino)coumarin;3-(2'-Benzothiazolyl)-7-N,N-diethylaminocoumarin;3-(Benzothiazol-2-yl)-7-diethylamino-2H-benzopyran-2-one;Coumarin 540;Coumarin 6;NK 1858;NSC 290432;

Chemical Property of Coumarin 6

Chemical Property:

• Appearance/Colour: orange crystalline powder
• Vapor Pressure: 5.19E-13mmHg at 25°C
• Melting Point: 208-210 °C(lit.)
• Refractive Index: 1.69
• Boiling Point: 570.1 °C at 760 mmHg
• PKA: 2.98±0.20(Predicted)
• Flash Point: 298.6 °C
• PSA: 74.58000
• Density: 1.311 g/cm³
• LogP: 4.91590
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: DMF: soluble
• Water Solubility.: NEGLIGIBLE
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 350.10889899
• Heavy Atom Count: 25
• Complexity: 534

Purity/Quality:

99% ^*data from raw suppliers

Coumarin 6 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,C
• Statements: 20/21/22-36/37/38-34
• Safety Statements: 22-24/25-37/39-26-45-36/37/39-27

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Dyes -> Coumarin Dyes
• Canonical SMILES: CCN(CC)C1=CC2=C(C=C1)C=C(C(=O)O2)C3=NC4=CC=CC=C4S3
• Uses: Coumarin 6 is a member of 7-aminocoumarins. It has a role as a fluorochrome,can be as a fluorescent model drug. Coumarin 6 has been used as a hydrophobic fluorescent dyein block copolymer (BCP)-based micelle based drug delivery studies in glioma cell linesin combination with flufenamic acid (FA) based nanoprodrug uptake in glioma cellsin poly(lactic-co-glycolic acid) (PLGA) based elvitegravir nanoprodrug uptake studies

Technology Process of Coumarin 6

There total 19 articles about Coumarin 6 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: 100.0%

(η5-cyclopentadienyl)Ru(3-(2-benzothiazolyl)-7-(diethylamino)coumarin)(1+) → Coumarin 6 (38215-36-0) + cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate

Guidance literature:

In acetonitrile; Irradiation (UV/VIS); photolysis; not isolated;

Reference yield: 83.0%

ethyl 2-(2-benzothiazolyl)acetate (29182-42-1) + 4-(Diethylamino)salicylaldehyde (17754-90-4) → Coumarin 6 (38215-36-0)

Guidance literature:

With piperidine; In ethanol; at 160 ℃; for 0.333333h; Microwave irradiation; Sealed tube;

DOI:10.1016/j.tetlet.2019.151279

Reference yield: 72.0%

2-(benzo[d]thiazol-2-yl)acetic acid (29182-45-4) + 4-(Diethylamino)salicylaldehyde (17754-90-4) → Coumarin 6 (38215-36-0)

Guidance literature:

With 2-chloro-1-methyl-pyridinium iodide; triethylamine; In acetonitrile; Heating;

DOI:10.1081/SCC-200028575

upstream raw materials:

2-(benzo[d]thiazol-2-yl)acetic acid

4-(Diethylamino)salicylaldehyde

ethyl 2-(2-benzothiazolyl)acetate

ethyl 2-cyanoacetate

Downstream raw materials:

3-benzothiazol-2-yl-7-diethylamino-2-oxo-2H-chromene-4-carbonitrile

Refernces

• 1、 Park, Ji Eun,Choi, Myung Gil,Chang, Suk-Kyu. "Colorimetric and fluorescent signaling of Au3+ by desulfurization of thiocoumarin". . p. 2880 - 2884. Retrieved 2012.
• 2、 Zheng, Jinrong,Qin, Shuheng,Gui, Lijuan,Li, Hua,Fan, Lixue,Yang, Yifei,Chen, Haiyan,Xu, Hui,Yuan, Zhenwei. "Light-up lipid droplets for the visualization of lipophagy and atherosclerosis by coumarin-derived bioprobe". supporting information. p. 2385 - 2389. Retrieved 2021/03/17.
• 3、 Mah, Shinmee,Song, Daesun,Shin, Yongje,Jung, Yongwon,Hong, Sungwoo,Jang, Jaebong,Latif, Muhammad. "Discovery of fluorescent 3-heteroarylcoumarin derivatives as novel inhibitors of anaplastic lymphoma kinase". . p. 186 - 194. Retrieved 2019/01/11.