3-Cyano-7-hydroxycoumarin Chemical Properties

Melting point:

≥250 °C(lit.)

Boiling point:

436.6±45.0 °C(Predicted)

Density 

1.50±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMF: soluble

pka

7.03 ± 0.20, most acidic, temperature: 25 °C

form 

powder to crystal

color 

Yellow solid or powder

λmax

408 nm (Buffer pH 9); 408 nm (MeOH)

BRN 

153271

Major Application

Electroluminescentdevice;laser dyes; modified polyester for foodcontainers/beverage bottles; monitoring of cationicphotopolymerization processes;textiles;thin films

Biological Applications

Detectingmicroorganisms,nucleic acids; inhibiting cellproliferation/tumor growth; reference standard foresters; ethers,phosphates substrates; asa substrate for measuring nucleic acid polymerasesactivity; treating viral or parasite infections

InChIKey

IJQYTHQDUDCJEQ-UHFFFAOYSA-N

CAS DataBase Reference

19088-73-4

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

8

HS Code 

2932.20.4500

MSDS

• Language:English Provider:SigmaAldrich

3-Cyano-7-hydroxycoumarin Usage And Synthesis

Uses

3-Cyanoumbelliferone is a calibration standard.

Uses

3-Cyano-7-hydroxycoumarin has been the most widely used fluorophores for preparing fluorogenic substrates.As a blue-fluorescent probe used as a reference standard.

Synthesis

GENERAL METHOD: α-substituted ethyl acetate (1.0 mmol) and phenyl iododo diacetate (1.0 mmol) were dissolved in ethanol (5 mL) under continuous stirring conditions. After 10 min of reaction, benzaldehyde or salicylaldehyde (1.0 mmol) was added to the system and the reaction was continued with stirring until the appropriate time. The progress of the reaction was monitored by thin layer chromatography (TLC). After the TLC showed that the reaction was complete, the ethanol was evaporated under reduced pressure. Subsequently, the product was extracted with ethyl acetate and the organic phase was dried with anhydrous sodium sulfate (Na2SO4) and concentrated again under reduced pressure to remove the solvent. The resulting crude product was purified by recrystallization from a solvent mixture of ethyl acetate and hexane to finally obtain the target compound 7-hydroxy-2-oxochromene-3-carbonitrile (3a-3h and 4a-4r series derivatives).

References

[1] Synthetic Communications, 2005, vol. 35, # 6, p. 785 - 790
[2] Phosphorus, Sulfur and Silicon and the Related Elements, 2002, vol. 177, # 11, p. 2555 - 2559
[3] Tetrahedron Letters, 2017, vol. 58, # 32, p. 3183 - 3187
[4] Journal of Heterocyclic Chemistry, 2007, vol. 44, # 4, p. 867 - 870
[5] Journal of the Iranian Chemical Society, 2016, vol. 13, # 1, p. 149 - 153

3-Cyano-7-hydroxycoumarin(19088-73-4)Related Product Information

• CHLOROPHOSPHONAZO III
• 6-Hydroxycoumarin
• Esculetin
• Dihydrocoumarin
• 4-Hydroxycoumarin
• 7-Hydroxycoumarin
• Coumarin
• 4-Methylumbelliferone
• DICUMAROL
• 4-HYDROXY MEPHENYTOIN
• 3-Methoxypropionitrile
• Methyl cyanoacetate
• Cinnamonitrile
• 3-CYANOCOUMARIN
• 3-PHENOXYPROPIONITRILE
• Cyanoacetic acid
• CYANOACRYLIC ACID METHYL ESTER
• 2-PENTENENITRILE