38215-36-0

Basic information

• Product Name: Coumarin 6
• Synonyms: 3-(2'-BENZOTHIAZOLYL)-7-N,N-DIETHYLAMINOCOUMARIN;3-(2-BENZTHIAZOLYL)-7-DIETHYLAMINOCOUMARIN;3-(2-BENZOTHIAZOLYL)-7-(DIETHYLAMINO)COUMARIN;3-(2'-BENZOTHIAZOLYL)-7-DIETHYLAMINOCOUMARIN;3-(2-BENZOTHIAZOLYL)-N,N-DIETHYLUMBELLIFERYLAMINE;3-(1,3-BENZOTHIAZOL-2-YL)-7-(DIETHYLAMINO)-2H-CHROMEN-2-ONE;COUMARIN 540;COUMARIN 6
• CAS NO: 38215-36-0
• Molecular Formula: C₂₀H₁₈N₂O₂S
• Molecular Weight: 350.43
• EINECS: 253-830-2
• Product Categories: electronic;Electroluminescence;Functional Materials
• Mol File: 38215-36-0.mol
• Article Data: 16

Chemical Properties

• Melting Point: 208-210 °C(lit.)
• Boiling Point: 570.1 °C at 760 mmHg
• Flash Point: 298.6 °C
• Appearance: Orange/Powder
• Density: 1.1830 (rough estimate)
• Vapor Pressure: 5.19E-13mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: DMF: soluble
• PKA: 2.98±0.20(Predicted)
• Water Solubility: NEGLIGIBLE
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 1085798
• CAS DataBase Reference: Coumarin 6(CAS DataBase Reference)
• NIST Chemistry Reference: Coumarin 6(38215-36-0)
• EPA Substance Registry System: Coumarin 6(38215-36-0)

Safety Data

• 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
• WGK Germany: 3
• F: 8
• Hazardous Substances Data: 38215-36-0(Hazardous Substances Data)

Usage

Description

Coumarin 6, a member of the 7-aminocoumarins, is an orange crystalline powder known for its role as a fluorochrome. It is widely recognized for its stability in fluorescence spectroscopy, making it an ideal choice as a fluorescence lifetime standard. Coumarin 6 has gained significant attention due to its potential applications in various fields, particularly as a fluorescent model drug.

Uses

Used in Fluorescence Spectroscopy:
Coumarin 6 is used as a fluorescence lifetime standard in fluorescence spectroscopy for performing lifetime experiments. Its stability and reliability make it a preferred choice in this application.
Used in Pharmaceutical Research:
Coumarin 6 serves as a fluorescent model drug, aiding in the development and testing of new pharmaceutical compounds. Its fluorescent properties allow for better tracking and analysis of drug behavior within biological systems.
Used in Drug Delivery Systems:
In the field of drug delivery, Coumarin 6 is utilized as a hydrophobic fluorescent dye in block copolymer (BCP)-based micelle-based drug delivery studies. It helps in understanding the uptake and distribution of drugs within glioma cell lines when combined with flufenamic acid (FA) based nanoprodrugs.
Additionally, Coumarin 6 is employed in poly(lactic-co-glycolic acid) (PLGA) based elvitegravir nanoprodrug uptake studies, further enhancing the understanding of drug delivery mechanisms and improving the efficiency of drug administration.

InChI:InChI=1/C20H18N2O2S/c1-3-22(4-2)14-10-9-13-11-15(20(23)24-17(13)12-14)19-21-16-7-5-6-8-18(16)25-19/h5-12H,3-4H2,1-2H3

Upstream product

• 56278-50-3 2-cyanomethylbenzothiazole 
• 17754-90-4 4-(Diethylamino)salicylaldehyde 
• 137-07-5 2-amino-benzenethiol 
• 57597-64-5 7-diethylaminocoumarine-3-aldehyde 
• 20571-42-0 7-diethylamino-2H-benzopyran-2-one 
• 95-16-9 1,3-Benzothiazole 
• 133590-13-3 3-bromo-7-(diethylamino)-2H-chromen-2-one 
• 105-56-6 ethyl 2-cyanoacetate 
• 29182-42-1 ethyl 2-(2-benzothiazolyl)acetate 
• 29182-45-4 2-(benzo[d]thiazol-2-yl)acetic acid 

Downstream Products

• 70546-25-7 3-benzothiazol-2-yl-7-diethylamino-2-oxo-2H-chromene-4-carbonitrile 

Relevant articles and documents

Strong in vitro and vivo cytotoxicity of novel organoplatinum(II) complexes with quinoline-coumarin derivatives

A series of novel organoplatinum(II) complexes, [PtII(QC1)(H-QC1)Cl] (Pt1), [PtII(QC2)(H-QC2)Cl] (Pt2), [PtII(QC3)(H-QC3)Cl] (Pt3), [PtII(QC4)(H-QC4)Cl]?CH3OH (Pt4), [PtII(QC5)(H-QC5)Cl] (Pt5), [PtII(H-QC6)(DMSO)Cl2] (Pt6), [PtII(H-QC7)(DMSO)Cl2]?H2O (Pt7), [PtII(H-QC8)(DMSO)Cl2] (Pt8), [PtII(H-QC9)(DMSO)Cl2]?CH3OH (Pt9), [PtII(H-QC10)(DMSO)Cl2] (Pt10) and [PtII(H-QC11)(DMSO)Cl2] (Pt11), bearing quinoline-coumarin derivatives (H-QC1?H-QC11) have been first designed. Complexes Pt1–Pt11 selectively displayed obvious cytotoxicities in comparison to cisplatin for A549/DDP (cisplatin-resistant human lung adenocarcinoma) cells and HeLa cervical carcinoma cells, with IC50 values as low as 100 nM?10.33 μM. In addition, Pt4 and Pt5 display a green-colored luminescent properties, targeted mitochondrial membrane and, thereby induced mainly mitochondria-mediated cell apoptosis was in the following order: Pt4 > Pt5. The different anti-cancer activity of quinoline-coumarin complexes Pt4 (100 nM) and Pt5 (250 nM) were correlate with the presence of 3-(2′-quinolyl)-6-hydroxy-coumarin (H-QC4) ligand. The quinoline-coumarin complex Pt4 (2.0 mg/kg per 2 days) also displayed potent in vivo anti-tumor effect after 21 days-treated. In contrast, the H-QC4 ligand highly enhances the anti-tumor activity and selectivity of organoplatinum(II) complexes in comparison to other previously reported coumarin derivatives metal complexes.

Photoinduced formation of the laser dye coumarin 6 from its dihydro derivatives

The dihydro form of the laser dye Coumarin 6 and its acylated derivatives undergo photoinduced transformations with Coumarin 6 formation. The reactions go easily both in organic solvents and in polymer films with a high increase of fluorescence. Irreversibility of the reaction provides potential use of the new photosensitive media for optical information recording and sensing technologies.

Fluorescent 7-Substituted Coumarin Dyes: Solvatochromism and NLO Studies

The effect of three substituents N,N-diethylamine, carbazole and diphenylamine at the 7 position of coumarin on linear and nonlinear optical properties are studied using absorption and emission solvatochromism, and DFT. By varying the substituent 53?nm red shift is achieved in emission. The polarity plots with regression close to unity revealed good charge transfer in the system. Solvent polarizability and dipolarity are mainly responsible for solvatochromic shift as proved by multilinear regression analysis. General Mulliken Hush analysis shows diphenylamine substituent leads to more charge separation in compound 6c. The hyperpolarizabilities are evaluated by quantum mechanical calculations. Structure of the compounds are optimized at B3LYP/6-31G(d) level and NLO computations are done using range separated hybrid functionals with large basis sets. Second order hyperpolarizability (γ) found 589.27 × 10?36, 841.29 × 10?36 and 1043.00 × 10?36 e.s.u for the compounds 6a, 6b and 6c respectively.

Reinvestigation of the synthesis of “covalent-assembly” type probes for fluoride ion detection. Identification of novel 7-(diethylamino)coumarins with aggregation-induced emission properties

An unprecedented C-3 functionalization of 4-(diethylamino)salicylaldehyde through a Friedel-Crafts type alkylation reaction has been discovered during the synthesis of “covalent-assembly”-based fluorescent probes for detection of fluoride ions. The resulting Friedel-Crafts adduct was successfully used for the preparation of two novel 8-substituted 7-(diethylamino)coumarin dyes. The photophysical study of these fluorophores has enabled us to highlight their remarkable aggregation-induced emission (AIE) properties characterized by a yellow-orange emission of aggregates in water. Therefore, 4-(tert-butyldimethylsilyloxy)benzyl substituent was identified as a novel AIE-active moiety which could be seen as a possible alternative to popular tetraphenylethylene (TPE).