104451-70-9 | 2,3,6-Trifluorobenzaldehyde

CAS:104451-70-9 | 2,3,6-Trifluorobenzaldehyde,Description

Synthesis Analysis

The synthesis of fluorinated benzaldehydes like 2,3,6-Trifluorobenzaldehyde often involves direct fluorination strategies or the substitution of other functional groups with fluorine. A related synthesis approach involves the preparation of 2,6-difluorobenzaldehyde from 2,6-dichlorobenzaldehyde using KF in tetramethylene sulfoxide, followed by purification through fractionation. The process parameters such as the mole ratio of KF to dichlorobenzaldehyde, reaction volume, and temperature are optimized to achieve high yields and purity (Wang Ya-lou, 2004)[https://consensus.app/papers/synthesis-26difluorobenzaldehyde-yalou/c649590ebd6e56c6af371b02cefb2e4a/?utm_source=chatgpt].

Molecular Structure Analysis

Fluorinated benzaldehydes exhibit unique molecular structures due to the electron-withdrawing nature of fluorine atoms. These structures can be analyzed using techniques such as X-ray crystallography, nuclear magnetic resonance (NMR), and infrared (IR) spectroscopy. The presence of fluorine atoms influences the electronic distribution within the molecule, affecting its reactivity and interactions with other molecules.

Chemical Reactions and Properties

2,3,6-Trifluorobenzaldehyde participates in various chemical reactions, leveraging the reactivity of the aldehyde group and the influence of the fluorine substituents. For instance, hydroxybenzaldehydes can undergo reactions with alkynes, alkenes, or allenes in the presence of a rhodium catalyst, leading to the formation of alkenoylphenols (Ken Kokubo et al., 1999)[https://consensus.app/papers/reaction-2hydroxybenzaldehydes-alkynes-alkenes-allenes-kokubo/62f2bf8d3c895049a1879d4cbbe2cc2c/?utm_source=chatgpt]. These reactions demonstrate the utility of fluorinated benzaldehydes in synthesizing complex organic compounds.

Scientific Research Applications

• Antioxidant, Enzyme Inhibition, and Antibacterial/Antifungal Activities : When coordinated with metal ions, 2,3,6-Trifluorobenzaldehyde shows antioxidant, enzyme inhibition, and antibacterial/antifungal activities. This was discussed in the paper "Metal based triazole compounds: Their synthesis, computational, antioxidant, enzyme inhibition and antimicrobial properties" by Sumrra et al. (2018) in the Journal of Molecular Structure (Sumrra et al., 2018).
• Spectroscopy Research : The vapors of 2,3,6-Trifluorobenzaldehyde are used in measuring emission and absorption spectra. This application is detailed in the study "Emission and absorption spectra of 2,3,4-, 2,3,5- and 2,4,5-trifluorobenzaldehyde vapors" by T. Itoh (2010) in the Journal of Molecular Spectroscopy (Itoh, 2010).
• Linker in Solid Phase Organic Synthesis : It is used as a linker in solid phase organic synthesis, as explored in the paper "Secondary amide-based linkers for solid phase organic synthesis" by E. Swayze (1997) in Tetrahedron Letters (Swayze, 1997).
• Nutraceutical Potential : 2,4,6-Trihydroxybenzaldehyde, a related compound, has shown potential as a nutraceutical to help prevent or treat obesity and its associated metabolic disorders. This was studied in "2,4,6-Trihydroxybenzaldehyde, a potential anti-obesity treatment, suppressed adipocyte differentiation in 3T3-L1 cells and fat accumulation induced by high-fat diet in C57BL/6 mice" by Kim et al. (2015) in Environmental Toxicology and Pharmacology (Kim et al., 2015).

Safety And Hazards

Safety data indicates that 2,3,6-Trifluorobenzaldehyde may cause skin irritation, serious eye irritation, and may cause respiratory irritation. It is recommended to avoid breathing dust/fume/gas/mist/vapors/spray and to use only outdoors or in a well-ventilated area. Protective gloves, protective clothing, eye protection, and face protection should be worn when handling this compound.

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