Coumarin 314

Name: Coumarin 314
Brand: Zhengzhou Whchem

CAS：55804-66-5 | Coumarin 314 | Whchem

CAS: 55804-66-5

Other Names

ethyl 2,3,6,7-tetrahydro-11-oxo-1H,5H,11H-[1]benzopyrano[6,7,8-ij]quinolizine-10-carboxylate;COUMARIN 314, DYE CONTENT 99+%;Coumarin 314, laser grade, pure, 99%;2,3,5,6-1h,4h-tetrahydro-9-carbethoxyquinolizino-[9,9a,1-gh]coumarin;Exciton Coumarin 504;Coumarin 504, 2,3,5,6-1H,4H-Tetrahydro-9-carbethoxyquinolizino-[9,9a,1-gh]coumarin;11-Oxo-2,3,6,7-tetrahydro-1H,5H,11H-[1]benzopyrano[6,7,8-ij]quinolizine-10-carboxylic acid ethyl ester;2,3,6,7-Tetrahydro-11-oxo-1H,5H,11H-[1]benzopyrano[6,7,8-ij]quinolizine-10-carboxylic acid ethyl ester

Molecular Formula

Purity

>98%

Molecular Weight

313.35 g/mol

EINECS

259-825-1

Structure Available Verified Product

English Name	Coumarin 314
English Synonyms	ethyl 2,3,6,7-tetrahydro-11-oxo-1H,5H,11H-[1]benzopyrano[6,7,8-ij]quinolizine-10-carboxylate;COUMARIN 314, DYE CONTENT 99+%;Coumarin 314, laser grade, pure, 99%;2,3,5,6-1h,4h-tetrahydro-9-carbethoxyquinolizino-[9,9a,1-gh]coumarin;Exciton Coumarin 504;Coumarin 504, 2,3,5,6-1H,4H-Tetrahydro-9-carbethoxyquinolizino-[9,9a,1-gh]coumarin;11-Oxo-2,3,6,7-tetrahydro-1H,5H,11H-[1]benzopyrano[6,7,8-ij]quinolizine-10-carboxylic acid ethyl ester;2,3,6,7-Tetrahydro-11-oxo-1H,5H,11H-[1]benzopyrano[6,7,8-ij]quinolizine-10-carboxylic acid ethyl ester
CAS Number	55804-66-5
Molecular Formula	C18H19NO4
Molecular Weight	313.35 g/mol
EINECS Number	259-825-1
Related Categories
Mol File	Download MOL File
Structure Image

Property	Value
Melting point	140-144 °C (lit.)
Boiling point	453.15°C (rough estimate)
Density	1.2389 (rough estimate)
Refractive index	1.5100 (estimate)
Storage condition	Room temperature
Acidity Coefficient (pKa)	5.37±0.40 (Predicted)
Form	Crystalline powder
Color	Viscous yellow
Extinction Coefficient (ε)	≥39000 at 389-401 nm in ethanol at 0.01 g/L
Maximum Wavelength (λmax)	436 nm, 437 nm in ethanol
Major applications	Diagnostic assay manufacturing, hematology, histology
InChI	InChI=1S/C18H19NO4/c1-2-22-17(20)14-10-12-9-11-5-3-7-19-8-4-6-13(15(11)19)16(12)23-18(14)21/h9-10H,2-8H2,1H3
InChIKey	VMJKUPWQKZFFCX-UHFFFAOYSA-N
SMILES	CCOC(=O)C1=Cc2cc3CCCN4CCCc(c2OC1=O)c34
EPA Chemical Substance Reference	1H,5H,11H-[1]Benzopyrano[6,7,8-ij]quinolizine-10-carboxylic acid, 2,3,6,7-tetrahydro-11-oxo-, ethyl ester (55804-66-5)

Coumarin 314 (CAS 55804-66-5) is a high-purity fine chemical intermediate widely used in organic synthesis, pharmaceutical R&D, agrochemical manufacturing and specialty chemical applications.

As a professional supplier, Zhengzhou Whchem provides Coumarin 314 with >98% purity, COA, structure confirmation and flexible packaging, available from research quantities to commercial scale with global shipping.

Category	Description (English Translation)
Uses & Synthesis Methods Overview: Coumarin 314 is a fluorescent dye. Coumarin fluorescent dyes are an important class of fluorescent dyes. Due to their high fluorescence quantum yields, large Stokes shifts, and good photostability, they have broad applications in the field of fluorescent dyes. Naphthalimide fluorescent dyes are also an important class of fluorescent dyes; similarly, naphthalimides also possess high fluorescence quantum yields, large Stokes shifts, and good photostability, making them suitable for various applications in fluorescence-based technologies. Preparation Procedure: Step 1: Compound 1 (5.5 g) was dissolved in 200 mL of ethanol. n-Butylamine (2.4 mL) was added with stirring, and the mixture was heated at 90°C for 12 hours. After cooling to room temperature, a large amount of needle-like crystals of compound 2 precipitated. Step 2: Compound 2 (2.0 g) was dissolved in 10 mL of ethylene glycol monomethyl ether. Hydrazine hydrate (80%, 2 mL) was added dropwise with stirring, and the mixture was heated at 120°C for 4 hours. The product was collected by suction filtration to give compound 3. Step 3: Compound 3 (1.0 g) was dissolved in 20 mL of 3-methyl-2-butanone with stirring. Concentrated sulfuric acid (1.5 mL) was added slowly dropwise, and the mixture was heated at 90°C for 4 hours. After removing excess solvent by rotary evaporation, 5 mL of ethanol was added. After standing for 30 minutes, a large amount of precipitate formed, which was collected by suction filtration. The filter cake was dispersed in 5 mL of ethanol, and a small amount of ammonia water was added with stirring. The suspension was poured into water to precipitate the product, which was collected by suction filtration to give compound 4. Step 4: DMF (8 mL) was slowly added dropwise to POCl₃ (2.66 mL) in an ice bath with stirring for 15 minutes. Compound 5 (4.6 g) was dissolved in 5 mL of DMF, and this solution was slowly added dropwise to the above mixture. The mixture was stirred in an ice bath for 30 minutes, then heated to 70°C and stirred for 2 hours. After cooling to room temperature, the reaction mixture was poured into 25 mL of water, and the product was collected by suction filtration to give compound 6. Step 5: Compound 6 (3.86 g) was dissolved in 30 mL of ethanol. Diethyl malonate (6.4 mL) and piperidine (1.5 mL) were added, and the mixture was heated at 85°C for 3 hours. After removing excess solvent by rotary evaporation, compound 7 (Coumarin 314) was obtained.

Category

Description (English Translation)

Uses & Synthesis Methods

Overview: Coumarin 314 is a fluorescent dye. Coumarin fluorescent dyes are an important class of fluorescent dyes. Due to their high fluorescence quantum yields, large Stokes shifts, and good photostability, they have broad applications in the field of fluorescent dyes. Naphthalimide fluorescent dyes are also an important class of fluorescent dyes; similarly, naphthalimides also possess high fluorescence quantum yields, large Stokes shifts, and good photostability, making them suitable for various applications in fluorescence-based technologies.

Preparation Procedure:

Step 1: Compound 1 (5.5 g) was dissolved in 200 mL of ethanol. n-Butylamine (2.4 mL) was added with stirring, and the mixture was heated at 90°C for 12 hours. After cooling to room temperature, a large amount of needle-like crystals of compound 2 precipitated.

Step 2: Compound 2 (2.0 g) was dissolved in 10 mL of ethylene glycol monomethyl ether. Hydrazine hydrate (80%, 2 mL) was added dropwise with stirring, and the mixture was heated at 120°C for 4 hours. The product was collected by suction filtration to give compound 3.

Step 3: Compound 3 (1.0 g) was dissolved in 20 mL of 3-methyl-2-butanone with stirring. Concentrated sulfuric acid (1.5 mL) was added slowly dropwise, and the mixture was heated at 90°C for 4 hours. After removing excess solvent by rotary evaporation, 5 mL of ethanol was added. After standing for 30 minutes, a large amount of precipitate formed, which was collected by suction filtration. The filter cake was dispersed in 5 mL of ethanol, and a small amount of ammonia water was added with stirring. The suspension was poured into water to precipitate the product, which was collected by suction filtration to give compound 4.

Step 4: DMF (8 mL) was slowly added dropwise to POCl₃ (2.66 mL) in an ice bath with stirring for 15 minutes. Compound 5 (4.6 g) was dissolved in 5 mL of DMF, and this solution was slowly added dropwise to the above mixture. The mixture was stirred in an ice bath for 30 minutes, then heated to 70°C and stirred for 2 hours. After cooling to room temperature, the reaction mixture was poured into 25 mL of water, and the product was collected by suction filtration to give compound 6.

Step 5: Compound 6 (3.86 g) was dissolved in 30 mL of ethanol. Diethyl malonate (6.4 mL) and piperidine (1.5 mL) were added, and the mixture was heated at 85°C for 3 hours. After removing excess solvent by rotary evaporation, compound 7 (Coumarin 314) was obtained.

Category	Value
Hazard Symbol	Xn
Hazard Codes (R Phrases)	36/37/38-20/21/22
Safety Codes (S Phrases)	37/39-26
WGK Germany	3
TSCA	TSCA listed
HS Code (Customs)	29322985
Storage Category	11 - Combustible solids

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Coumarin 314

CAS：55804-66-5 | Coumarin 314 | Whchem

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