364-83-0 | 2',4'-Difluoroacetophenone

CAS:364-83-0 | 2',4'-Difluoroacetophenone,Description

2',4'-Difluoroacetophenone is a chemical compound that has been studied for its potential applications in various fields, including pharmaceuticals and materials science. The compound is characterized by the presence of two fluorine atoms attached to the benzene ring, which can significantly alter its chemical and physical properties compared to its non-fluorinated analogs.

Synthesis Analysis

Several methods have been developed to synthesize derivatives of 2',4'-difluoroacetophenone. One approach involves the Suzuki coupling reaction, which is a popular method for forming carbon-carbon bonds and has been used to synthesize a potent COX-2 inhibitor with a difluorophenyl moiety. Another synthesis method described involves cross-coupling of 2',4'-difluorophenylboronic acid with 4-bromoacetophenone, mediated by a Pd(II) complex, which resulted in high yields and is considered practical for industrial applications. Additionally, a Friedel-Crafts acylation has been employed to synthesize a liquid crystal intermediate with difluoroacetophenone structure, demonstrating the versatility of this compound in materials science.

Molecular Structure Analysis

The molecular structure of 2',4'-difluoroacetophenone has been characterized using various spectroscopic techniques. Single crystal X-ray diffractometry, along with IR and 1H NMR spectroscopy, has been used to confirm the structure of synthesized 4-(2',4'-difluorophenyl)acetophenone. Furthermore, a comprehensive analysis of the molecular structure, including spectroscopic (FTIR, FT-Raman, 13C and 1H NMR, UV), polarizability, and first-order hyperpolarizability, as well as HOMO-LUMO analysis, has been conducted for 2,4-difluoroacetophenone, providing detailed insights into the electronic properties of the molecule.

Chemical Reactions Analysis

The reactivity of difluoroacetophenone derivatives has been explored in various chemical reactions. For instance, the synthesis of α-bromo-4-(difluoromethylthio)acetophenone and its subsequent condensation with different azaheterocycles has been studied, leading to the formation of S- and N-substituted azaheterocycles containing the difluoromethylthio phenyl fragment. This highlights the potential of difluoroacetophenone derivatives to act as intermediates in the synthesis of complex organic molecules.

Physical and Chemical Properties Analysis

The physical and chemical properties of 2',4'-difluoroacetophenone derivatives are influenced by the presence of fluorine atoms. The fluorine substituents can affect the acidity, basicity, and overall reactivity of the molecule. The polarizability and first hyperpolarizability of 2,4-difluoroacetophenone have been calculated, indicating the molecule's potential applications in nonlinear optics. The molecular electrostatic potential map also provides information on the reactive sites of the molecule, which is useful for predicting its behavior in chemical reactions.

Scientific Research Applications

Application 1: Synthesis of Difluorinated Chalcones

• Summary of the Application: 2’,4’-Difluoroacetophenone is used as a starting reagent in the synthesis of difluorinated chalcones.

Application 2: Vibrational Spectral Analysis

• Summary of the Application: 2’,4’-Difluoroacetophenone is used in the field of physical chemistry for vibrational spectral analysis. This type of analysis is important for understanding the molecular structure and dynamics of a compound.
• Methods of Application or Experimental Procedures: The vibrational spectral analysis of 2’,4’-Difluoroacetophenone is carried out by Fourier Transform Infrared (FT-IR) and Fourier Transform Raman (FT-Raman) spectroscopy. These techniques involve passing a beam of light through a sample and measuring the intensity of light that is absorbed or scattered at different wavelengths.
• Results or Outcomes: The results of this analysis provide valuable information about the vibrational modes of the molecule, which can be used to infer details about its structure and dynamics.

Safety And Hazards

2’,4’-Difluoroacetophenone is classified as a combustible liquid. It causes skin irritation and serious eye irritation. It may also cause respiratory irritation.

Relevant Papers One relevant paper discusses the lithium triethylborohydride-promoted generation of α,α-difluoroenolates from 2-iodo-2,2-difluoroacetophenones. This represents an unprecedented utilization of lithium triethylborohydride.

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