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442631

Sigma-Aldrich

Coumarin 6

98%

Synonym(s):

3-(2-Benzothiazolyl)-7-(diethylamino)coumarin, 3-(2-Benzothiazolyl)-N,N-diethylumbelliferylamine

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About This Item

Empirical Formula (Hill Notation):
C20H18N2O2S
CAS Number:
38215-36-0
Molecular Weight:
350.43
Beilstein:
1085798
EC Number:
253-830-2
MDL number:
MFCD00041869
UNSPSC Code:
12352103
PubChem Substance ID:
24867935
NACRES:
NA.23

Quality Level

100

Assay

98%

form

solid

mp

208-210 °C (lit.)

λmax

444 nm

fluorescence

λem 505 nm in ethanol (Lasing peak 534 nm, lasing range 515 - 558 nm (DMSO), pump source XeCl (308 nm))

OLED Device Performance

ITO/Alq3:Coumarin 6/Mg:Ag

  • Color: green
  • Max. EQE: 2.5 %

SMILES string

CCN(CC)c1ccc2C=C(C(=O)Oc2c1)c3nc4ccccc4s3

InChI

1S/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

InChI key

VBVAVBCYMYWNOU-UHFFFAOYSA-N

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General description

Coumarin 6 (C6) is a derivative of coumarin with a benzothiazolyl group at the position 3. It emits fluorescence in solid and solution state and is used as fluorescent dye to stain organelles. C6 is majorly used as blue-green spectrum laser dye and is microenvironment sensitive.
Coumarin 6 is a fluorescent dye that belongs to the 7-diethylaminocoumarin series that can be used in a variety of biological activities. It can be used as a dopant that exhibits green light (500 nm) in optoelectronic applications.

Application

Coumarin 6 dye can be used in the labeling and visualization of polymeric nanoparticles in biological applications, such as oral drug delivery systems for cancer. It can also be used in development of electroluminescent devices such as organic light emitting diodes (OLEDs).
Coumarin 6 has been used as a hydrophobic fluorescent dye
  • in block copolymer (BCP)-based micelle based drug delivery studies in glioma cell lines
  • in combination with flufenamic acid (FA) based nanoprodrug uptake in glioma cells
  • in poly(lactic-co-glycolic acid) (PLGA) based elvitegravir nanoprodrug uptake studies

Laser dye

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000415933
0000415933
0000400879
0000377735
0000346999

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Surface modification of indium tin oxide by plasma treatment: An effective method to improve the efficiency, brightness, and reliability of organic light emitting devices.
Wu CC, et al.
Applied Physics Letters, 70(11), 1348-1350 (1997)
Novel elvitegravir nanoformulation approach to suppress the viral load in HIV-infected macrophages
Gong Y, et al.
Biochemistry and Biophysics Reports, 12, 214-219 (2017)
Photophysical and photochemical properties of Coumarin-6 molecules incorporated within MCM-48
Li D, et al.
Materials Letters, 59(17), 2120-2123 (2005)
Effects of particle size and surface coating on cellular uptake of polymeric nanoparticles for oral delivery of anticancer drugs.
Win KY and Feng S
Biomaterials, 26(15), 2713-2722 (2005)
White light-emitting organic electroluminescent devices using the poly (N-vinylcarbazole) emitter layer doped with three fluorescent dyes.
Kido J, et al.
Applied Physics Letters, 64(7), 815-817 (1994)
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