3-Benzoyl-7-diethylaminocoumarin
[CAS# 77016-78-5]

Identification

• Classification: Organic raw materials >> Amino compound >> Amide compound
• Name: 3-Benzoyl-7-diethylaminocoumarin
• Molecular Formula: C₂₀H₁₉NO₃
• Molecular Weight: 321.37
• CAS Registry Number: 77016-78-5
• SMILES: CCN(CC)C1=CC2=C(C=C1)C=C(C(=O)O2)C(=O)C3=CC=CC=C3

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.625, Calc.^*
• Boiling Point: 524.1±50.0 ºC (760 mmHg), Calc.^*
• Flash Point: 270.8±30.1 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P280-P305+P351+P338

Discovory and Applicatios

3-Benzoyl-7-diethylaminocoumarin is a notable compound in the field of organic chemistry, particularly valued for its applications as a fluorescent dye. This substance, a derivative of coumarin, is recognized for its vivid fluorescence properties, which make it a valuable tool in various scientific and industrial applications.

The discovery of 3-benzoyl-7-diethylaminocoumarin dates back to research aimed at developing new fluorescent dyes with enhanced spectral properties. Coumarins, known for their fluorescence, have long been studied for their potential in imaging and detection applications. The introduction of the benzoyl group and the diethylamino moiety to the coumarin structure was a strategic modification designed to improve the dye's fluorescence efficiency and spectral characteristics.

The compound's structure consists of a coumarin backbone, modified with a benzoyl group at the 3-position and a diethylamino group at the 7-position. These substitutions significantly influence the electronic properties of the molecule, resulting in enhanced fluorescence. The benzoyl group increases the rigidity of the coumarin ring system, which helps in stabilizing the excited-state configuration and improving the quantum yield. Meanwhile, the diethylamino group acts as an electron-donating substituent, further enhancing the dye's fluorescence by increasing the electron density around the coumarin core.

3-Benzoyl-7-diethylaminocoumarin finds extensive use in fluorescence microscopy and spectroscopy due to its strong and stable fluorescence emission. In fluorescence microscopy, it is employed as a staining agent for labeling various biological specimens. The dye's high quantum yield and distinct emission spectra make it ideal for imaging applications, allowing researchers to visualize and track cellular components and processes with high sensitivity and resolution.

In addition to its role in biological imaging, 3-benzoyl-7-diethylaminocoumarin is utilized in the development of fluorescent probes and sensors. These probes are designed to detect specific analytes or environmental changes based on fluorescence emission. For example, the dye can be incorporated into sensor systems that monitor pH changes, metal ion concentrations, or the presence of specific molecules. The fluorescence properties of the dye allow for precise and real-time measurements, which are valuable in both research and industrial settings.

The dye also has applications in the field of analytical chemistry, where it is used as a fluorescent tag in various assays and detection methods. Its ability to produce strong and reliable fluorescence signals makes it a preferred choice for enhancing the sensitivity and accuracy of analytical techniques. This includes its use in high-performance liquid chromatography (HPLC) and other chromatographic methods, where it aids in the detection and quantification of trace compounds.

Overall, 3-benzoyl-7-diethylaminocoumarin represents a significant advancement in the development of fluorescent dyes. Its enhanced fluorescence properties and versatility make it a valuable tool in scientific research, biological imaging, and analytical applications. The continued study and application of this compound underscore its importance in advancing various fields that rely on fluorescence-based technologies.