456-04-2 | 2-Chloro-4'-fluoroacetophenone

CAS:456-04-2 | 2-Chloro-4'-fluoroacetophenone,Description

2-Chloro-4'-fluoroacetophenone is a chemical compound that has been the focus of various scientific studies due to its relevance in chemical synthesis and potential applications in materials science and pharmaceutical chemistry. The compound is known for its unique properties, which arise from the presence of both chloro and fluoro substituents on the acetophenone structure.

Synthesis Analysis

The synthesis of related compounds often involves reacting halogenated acetophenones with other organic compounds in the presence of catalysts. For example, (E)-3-(4-Chlorophenyl)-1-(4-fluorophenyl)prop-2-en-1-one is synthesized by reacting 4-fluoroacetophenone and 4-chlorobenzaldehyde in ethanol with sodium hydroxide as a catalyst. This method highlights a common approach to synthesizing chloro and fluoro-substituted acetophenones, which may be adapted for 2-Chloro-4'-fluoroacetophenone (Najiya et al., 2014).

Molecular Structure Analysis

The molecular structure of chloro- and fluoro-substituted acetophenones has been extensively studied using various analytical methods, including FT-IR, NMR, and X-ray crystallography. These studies provide insights into the geometric parameters, vibrational frequencies, and electronic properties of the molecules. For instance, the molecular structure and vibrational wavenumbers of (E)-3-(4-Chlorophenyl)-1-(4-fluorophenyl)prop-2-en-1-one were determined through XRD and DFT methods, illustrating the compound's stability and electronic characteristics (Najiya et al., 2014).

Chemical Reactions and Properties

Chloro- and fluoro-substituted acetophenones participate in various chemical reactions, reflecting their electrophilic and nucleophilic properties. For instance, electrophilic fluorination and nucleophilic fluorination techniques have been applied to para-substituted acetophenones, highlighting the reactivity of these compounds under different conditions (Fuglseth et al., 2008).

Scientific Research Applications

Application 1: Synthesis of Imidazole Derivatives 

• Summary of the Application: 2-Chloro-4’-fluoroacetophenone is used in the synthesis of 1-methyl-2-(4-methylthio)phenyl-4-(4-fluoro)phenylimidazole. Imidazole derivatives have a wide range of applications in medicinal chemistry due to their diverse biological activities.
• Methods of Application: The compound is synthesized by condensing N-methyl-4-(methylthio)benzamidine with 2-Chloro-4’-fluoroacetophenone.

Application 2: Synthesis of S-(phenacyl)glutathiones

• Summary of the Application: 2-Chloro-4’-fluoroacetophenone is used in the synthesis of S-(phenacyl)glutathiones. Glutathione conjugates are involved in the detoxification of xenobiotics in the body.

Application 3: Synthesis of Fluvastatin

• Summary of the Application: 2-Chloro-4’-fluoroacetophenone is used in the synthesis of Fluvastatin, a medication used to treat high cholesterol.

Application 4: Synthesis of 2-[3-(4-chlorophenyl)-3-hydroxy-8-azabicyclo[3.2.1]oct-8-yl]-1-(4-fluorophenyl)ethanone 

• Summary of the Application: 2-Chloro-4’-fluoroacetophenone is used in the synthesis of 2-[3-(4-chlorophenyl)-3-hydroxy-8-azabicyclo[3.2.1]oct-8-yl]-1-(4-fluorophenyl)ethanone.

Application 5: Synthesis of Fluorine Ring Azoles

• Summary of the Application: 2-Chloro-4’-fluoroacetophenone is used in the synthesis of Fluorine Ring Azoles. These compounds are important in the field of agriculture.

Application 6: Synthesis of Agricultural Chemicals

• Summary of the Application: 2-Chloro-4’-fluoroacetophenone is used in the synthesis of various agricultural chemicals.

Safety And Hazards

2-Chloro-4’-fluoroacetophenone is considered hazardous. It is toxic if swallowed and may cause severe skin burns and eye damage. It may also cause an allergic skin reaction and is fatal if inhaled.

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