34036-07-2 | 3,4-Difluorobenzaldehyde

CAS:34036-07-2 | 3,4-Difluorobenzaldehyde,Description

Synthesis Analysis

The synthesis of difluorobenzaldehydes, including 3,4-difluorobenzaldehyde, can involve direct fluorination of benzaldehydes or through more complex synthetic routes involving precursor compounds. For instance, difluorobenzaldehyde was synthesized from 1,3-difluorobenzene and carbon monoxide with AlCl3 and HCl as catalysts under CO atmosphere, demonstrating the role of catalysts in directing the fluorination process and affecting yield and selectivity (Zhou Fengjun, 2005).

Molecular Structure Analysis

The molecular structure of benzene derivatives, including fluorinated compounds, has been extensively studied. Gas electron diffraction, microwave spectroscopy, and ab initio molecular orbital calculations have provided insights into their structure. For example, the molecular structure of gaseous 4-fluorobenzaldehyde has been determined, highlighting the importance of such analyses in understanding the geometric parameters and electronic structure of these compounds (S. Samdal et al., 1997).

Chemical Reactions and Properties

Fluorinated benzaldehydes undergo various chemical reactions due to the electron-withdrawing nature of the fluorine atoms, which significantly influences their reactivity. These compounds participate in nucleophilic addition reactions, condensation reactions, and can act as intermediates in the synthesis of more complex organic molecules. For example, the synthesis of 4-aryloxy-2,3,5,6-tetrafluorobenzaldehydes from pentafluorobenzaldehyde through nucleophilic substitution showcases the chemical versatility of fluorinated aldehydes (D. Gryko et al., 2008).

Physical Properties Analysis

The physical properties of 3,4-difluorobenzaldehyde, such as melting point, boiling point, and solubility, are influenced by the presence of fluorine atoms. These properties are crucial for determining the conditions under which these compounds can be handled and applied in various chemical processes. Studies on closely related compounds, utilizing techniques like matrix-isolation infrared spectroscopy, provide insights into the effects of fluorination on the physical properties of benzaldehydes (T. Itoh et al., 2011).

Scientific Research Applications

3,4-Difluorobenzaldehyde is a chemical compound with the molecular formula C7H4F2O. It is a colorless to light yellow to light orange clear liquid. It has a boiling point of 180 °C and a specific gravity of 1.31.

• Drug Discovery : 3,4-Difluorobenzaldehyde can be used as a building block in the synthesis of various pharmaceutical compounds.
• Organic Synthesis : It can be used in the synthesis of various organic compounds due to its reactivity.
• Material Science : It can also be used in the development of new materials.
• Synthesis of Fluorine-Substituted Analogs of Curcumin : 3,4-Difluorobenzaldehyde is used in the synthesis of fluorine-substituted analogs of Curcumin. Curcumin is a compound found in turmeric that has been studied for its potential chemopreventive and therapeutic effects against cancer.
• Synthesis of 3-Benzylidene 20,29-Dihydrobetulinic Acid Derivatives : 3,4-Difluorobenzaldehyde has been used in the synthesis of 3-benzylidene 20,29-dihydrobetulinic acid derivatives. These derivatives could have potential applications in medicinal chemistry.
• Preparation of 3,4-Difluorobenzaldehyde : A patentdiscloses a method for preparing 3,4-Difluorobenzaldehyde. The method includes carrying out a Grignard exchange reaction on 3,4-difluoro bromobenzene, tetrahydrofuran, and a Grignard reagent to obtain first reaction products. Then, a reaction is carried out on the first reaction products and N,N-dimethylformamide to obtain second reaction products, which are then treated to obtain the 3,4-Difluorobenzaldehyde.
• Synthesis of Novel Platelet-Aggregation-Resisting Medicament Ticagrelor : 3,4-Difluorobenzaldehydes are used as raw materials in the synthesis of Ticagrelor. Ticagrelor is a novel platelet-aggregation-resisting medicament developed by the U.S. AstraZeneca company.

Safety And Hazards

3,4-Difluorobenzaldehyde 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.

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