60611-24-7 | 2-FLUORO-6-(TRIFLUOROMETHYL)BENZALDEHYDE

CAS:60611-24-7 | 2-FLUORO-6-(TRIFLUOROMETHYL)BENZALDEHYDE,Description

2-Fluoro-6-(trifluoromethyl)benzaldehyde is a fluorinated aromatic compound that is of interest in various chemical research areas. The presence of fluorine atoms in the molecule is known to significantly affect its physical and chemical properties, as well as its reactivity. The trifluoromethyl group, in particular, can influence the molecule's conformation and intermolecular interactions, which can be crucial for understanding its behavior in different chemical contexts.

Synthesis Analysis

The synthesis of fluorinated aromatic compounds, such as 2-Fluoro-6-(trifluoromethyl)benzaldehyde, often involves the introduction of fluorine atoms or fluorine-containing groups into the aromatic ring. One approach to synthesizing fluorinated polyimides includes the use of a fluorine-containing aromatic diamine, which is reacted with aromatic dianhydrides. This process involves the reduction of a dinitro-compound synthesized by coupling a chloro-nitro-trifluoromethylbenzene with a diol in the presence of a strong base. Although not directly related to the synthesis of 2-Fluoro-6-(trifluoromethyl)benzaldehyde, this method provides insight into the general strategies used to incorporate fluorine into aromatic compounds.

Molecular Structure Analysis

The molecular structure of fluorinated compounds is often characterized by the presence of strong and weak intermolecular interactions. In the case of trifluoromethylated benzanilides, which share some structural similarities with 2-Fluoro-6-(trifluoromethyl)benzaldehyde, the presence of a trifluoromethyl group can lead to a variety of supramolecular arrangements. These arrangements are influenced by intermolecular interactions such as hydrogen bonds and the "fluorous effect," which involves C-F...F-C contacts. The trifluoromethyl group can also induce conformational flexibility and rotational disorder in crystalline solids.

Chemical Reactions Analysis

The reactivity of benzaldehydes, including those that are fluorinated, can be explored through various chemical reactions. For instance, deoxyfluorination of benzaldehydes can be achieved at room temperature using sulfuryl fluoride and tetramethylammonium fluoride. This method demonstrates the potential for selective fluorination of aromatic aldehydes, which could be applicable to 2-Fluoro-6-(trifluoromethyl)benzaldehyde. Additionally, benzaldehydes can undergo C-H functionalization reactions, as shown in the synthesis of fluorenones from benzaldehydes and aryl iodides using a palladium-catalyzed process.

Physical and Chemical Properties Analysis

The physical and chemical properties of fluorinated aromatic compounds are significantly influenced by the fluorine atoms. For example, the synthesis of fluoro-polyimides from fluorinated diamines results in materials with excellent thermal stability, low moisture absorption, and high hygrothermal stability. The conformational analysis of fluorinated benzaldehydes reveals that the presence of fluorine can lead to planar structures with the trans conformer being more stable. This stability is influenced by the solvent's polarity, and the overall molecular geometry can affect the compound's physical properties.

Scientific Research Applications

• Synthesis of 2-amino-5-trifluoromethylquinazoline 
  • Application : 2-Fluoro-6-(trifluoromethyl)benzaldehyde is used in the synthesis of 2-amino-5-trifluoromethylquinazoline. Quinazolines are a class of organic compounds with a wide range of biological activities and are used in the development of pharmaceuticals.
• Synthesis of diaryl ether and 2-(3,5-dimethoxyphenoxy)-6-(trifluoromethyl)benzonitrile 
  • Application : 2-Fluoro-6-(trifluoromethyl)benzaldehyde can be used in the synthesis of diaryl ether and 2-(3,5-dimethoxyphenoxy)-6-(trifluoromethyl)benzonitrile. Diaryl ethers are used in a variety of applications, including as intermediates in organic synthesis.
• Synthesis of substituted benzo[b]thiophene-2-carboxylates 
  • Application : 2-Fluoro-6-(trifluoromethyl)benzaldehyde is used in the synthesis of substituted benzo[b]thiophene-2-carboxylates. Benzo[b]thiophene derivatives have been studied for their potential biological activities.

Safety And Hazards

This chemical is considered hazardous by the 2012 OSHA Hazard Communication Standard (29 CFR 1910.1200). It is classified as a flammable liquid, can cause skin irritation and serious eye irritation, and may cause respiratory irritation.

Future Directions

The future directions of 2-Fluoro-6-(trifluoromethyl)benzaldehyde could involve its use in the synthesis of various compounds, as it has been employed for the synthesis of diaryl ether, 2-(3,5-dimethoxyphenoxy)-6-(trifluoromethyl)-benzonitrile, and substituted benzo[b]thiophene-2-carboxylates.

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