| Identification | Back Directory | [Name]
3-Cyano-7-hydroxycoumarin | [CAS]
19088-73-4 | [Synonyms]
3-CYANOUMBELLIFERONE
3-Cyanoumbelliferone>
3-CYANO-7-HYDROXYCOUMARIN
3-Cyano-7-hydroxycoumarin 95+%
7-Hydroxy-2-oxochromene-3-carbonitrile
3-CYANOUMBELLIFERONE, FOR FLUORESCENCE*
7-hydroxy-2-oxo-2H-chromene-3-carbonitrile
3-Cyano-7-hydroxycoumarin *CAS 19088-73-4*
7-hydroxy-2-oxo-1-benzopyran-3-carbonitrile
3-Cyano-7-hydroxycoumarin ISO 9001：2015 REACH
2H-1-Benzopyran-3-carbonitrile, 7-hydroxy-2-oxo-
3-CyanouMbelliferone [3-Cyano-7-hydroxycouMarin] | [EINECS(EC#)]
200-123-4 | [Molecular Formula]
C10H5NO3 | [MDL Number]
MFCD00037480 | [MOL File]
19088-73-4.mol | [Molecular Weight]
187.15 |
| Chemical Properties | Back Directory | [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
| [form ]
powder to crystal | [pka]
7.03 ± 0.20, most acidic, temperature:
25 °C | [color ]
Yellow solid or powder | [λmax]
408 nm (Buffer pH 9); 408 nm
(MeOH) | [BRN ]
153271 | [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 | [Major Application]
Electroluminescentdevice;laser dyes; modified polyester for foodcontainers/beverage bottles; monitoring of cationicphotopolymerization processes;textiles;thin films | [InChIKey]
IJQYTHQDUDCJEQ-UHFFFAOYSA-N | [CAS DataBase Reference]
19088-73-4 |
| Hazard Information | Back Directory | [Uses]
Blue-Fluorescent probe used as a reference 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 |
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Sigma-Aldrich
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https://www.sigmaaldrich.cn |
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