51473-74-6

Basic information

• Product Name: 3-CYANO-7-(DIETHYLAMINO)COUMARIN
• Synonyms: 3-CYANO-7-(DIETHYLAMINO)COUMARIN;RARECHEM AB KA K022;7-(Diethylamino)coumarin-3-carbonitrile;S2145
• CAS NO: 51473-74-6
• Molecular Formula: C₁₄H₁₄N₂O₂
• Molecular Weight: 242.27
• Mol File: 51473-74-6.mol
• Article Data: 20

Chemical Properties

• Melting Point: 228.0 to 232.0 °C
• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 3-CYANO-7-(DIETHYLAMINO)COUMARIN(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CYANO-7-(DIETHYLAMINO)COUMARIN(51473-74-6)
• EPA Substance Registry System: 3-CYANO-7-(DIETHYLAMINO)COUMARIN(51473-74-6)

Safety Data

• Hazardous Substances Data: 51473-74-6(Hazardous Substances Data)

Usage

Description

3-CYANO-7-(DIETHYLAMINO)COUMARIN is a fluorescent coumarin derivative characterized by the presence of a cyano group and a diethylamino group in its structure. These functional groups endow the compound with strong fluorescent properties, making it a valuable tool in various scientific and industrial applications.

Uses

Used in Fluorescent Detection:
3-CYANO-7-(DIETHYLAMINO)COUMARIN is used as a fluorescent probe for detecting metal ions due to its strong fluorescent activity. This property allows for its application in various analytical techniques, such as fluorescence spectroscopy and fluorescence microscopy, to monitor the presence and concentration of metal ions in different samples.
Used in Biological Applications:
In the biological field, 3-CYANO-7-(DIETHYLAMINO)COUMARIN is utilized as a fluorescent marker for studying cellular processes and interactions. Its fluorescent properties enable researchers to track and visualize specific biomolecules, proteins, or cellular structures, providing valuable insights into biological mechanisms and functions.
Used in Environmental Applications:
3-CYANO-7-(DIETHYLAMINO)COUMARIN has been studied for its potential use in environmental monitoring and analysis. Its ability to detect metal ions makes it a promising candidate for assessing water and soil quality, as well as monitoring the presence of heavy metals and other pollutants in the environment.
Used in Optoelectronic Devices and Sensors:
3-CYANO-7-(DIETHYLAMINO)COUMARIN has shown promise in the development of new materials for optoelectronic devices and sensors. Its strong fluorescent properties and sensitivity to metal ions make it a valuable component in the design and fabrication of advanced sensors for various applications, including environmental monitoring, medical diagnostics, and industrial process control.

Upstream product

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• 105-34-0 methyl 2-cyanoacetate 
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Downstream Products

• 20571-42-0 7-diethylamino-2H-benzopyran-2-one 
• 50995-74-9 7-(diethylamino)coumarin-3-carboxylic acid 

Relevant articles and documents

A new water-soluble two-photon fluorescent probe for detection of trace benzoyl peroxide in wheat flour and in living cell and tissue imaging

Benzoyl peroxide (BPO), a member of small-molecule reactive oxygen species (ROS), has attracted considerable attention because of its impact on human health and industrial importance. Herein, to quantitatively detect BPO in real samples and for fluorescen

A Minimalistic Coumarin Turn-On Probe for Selective Recognition of Parallel G-Quadruplex DNA Structures

G-quadruplex (G4) DNA structures are widespread in the human genome and are implicated in biologically important processes such as telomere maintenance, gene regulation, and DNA replication. Guanine-rich sequences with potential to form G4 structures are prevalent in the promoter regions of oncogenes, and G4 sites are now considered as attractive targets for anticancer therapies. However, there are very few reports of small "druglike"optical G4 reporters that are easily accessible through one-step synthesis and that are capable of discriminating between different G4 topologies. Here, we present a small water-soluble light-up fluorescent probe that features a minimalistic amidinocoumarin-based molecular scaffold that selectively targets parallel G4 structures over antiparallel and non-G4 structures. We showed that this biocompatible ligand is able to selectively stabilize the G4 template resulting in slower DNA synthesis. By tracking individual DNA molecules, we demonstrated that the G4-stabilizing ligand perturbs DNA replication in cancer cells, resulting in decreased cell viability. Moreover, the fast-cellular entry of the probe enabled detection of nucleolar G4 structures in living cells. Finally, insights gained from the structure-activity relationships of the probe suggest the basis for the recognition of parallel G4s, opening up new avenues for the design of new biocompatible G4-specific small molecules for G4-driven theranostic applications.

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).