251300-28-4 | 5-BROMO-3-FLUOROSALICYLALDEHYDE

CAS:251300-28-4 | 5-BROMO-3-FLUOROSALICYLALDEHYDE,Description

5-Bromo-3-fluoro-2-hydroxybenzaldehyde is a substituted benzaldehyde derivative that has been the subject of various studies due to its potential applications in organic synthesis and material science. The compound features a benzene ring with bromo, fluoro, and hydroxy substituents, as well as an aldehyde functional group, which makes it a versatile intermediate for chemical reactions and syntheses.

Synthesis Analysis

The synthesis of substituted benzaldehydes, including those with bromo and hydroxy substituents, has been explored through various methods. One approach involves a selective palladium-catalyzed ortho-bromination of benzaldehydes, using O-methyloxime as a directing group, followed by a rapid deprotection to yield substituted 2-bromobenzaldehydes with good overall yields. Another study reports the synthesis of 5-bromo-3-tert-butyl-2-hydroxy-benzaldehyde from 2-(tert-butyl)phenol, which could potentially be adapted for the synthesis of 5-bromo-3-fluoro-2-hydroxybenzaldehyde by introducing a fluoro substituent at the appropriate step.

Molecular Structure Analysis

The molecular structure of related compounds has been analyzed using various techniques. For instance, X-ray crystallographic analysis has been used to confirm the identity of 2-bromo-3-hydroxybenzaldehyde. A new polymorph of 2-bromo-5-hydroxybenzaldehyde has been reported, where the bromine atom deviates significantly from the plane of the benzene ring, and the aldehyde group is twisted around the Csp2–Caryl bond. These studies provide insights into the structural aspects of bromo- and hydroxy-substituted benzaldehydes, which are relevant for understanding the properties of 5-bromo-3-fluoro-2-hydroxybenzaldehyde.

Chemical Reactions Analysis

The reactivity of 5-bromo-2-hydroxybenzaldehyde has been studied in the context of its reaction with monomolecular layers of silanes immobilized on aluminum oxide surfaces, forming 5-bromo-2-hydroxybenzaldimine derivatives. This suggests that 5-bromo-3-fluoro-2-hydroxybenzaldehyde could similarly participate in condensation reactions due to the presence of the aldehyde group. Additionally, the synthesis of novel transition metal complexes with 5-bromo-2-fluorobenzaldehydeoxime indicates the potential for 5-bromo-3-fluoro-2-hydroxybenzaldehyde to form complexes with metals, which could be explored for antimicrobial applications.

Physical and Chemical Properties Analysis

While specific studies on the physical and chemical properties of 5-bromo-3-fluoro-2-hydroxybenzaldehyde are not provided, the properties of similar compounds can offer some insights. For example, the synthesis of 3-bromo-4-hydroxybenzaldehyde demonstrates the use of bromination agents and provides information on the reaction conditions that could affect the yield and purity of bromo-substituted benzaldehydes. The solubility, melting points, and spectral data of these compounds are crucial for their identification and application in further chemical syntheses.

Scientific Research Applications

Chemical Analysis and Separation Techniques

5-Bromo-3-fluoro-2-hydroxybenzaldehyde, a variant of bromo-hydroxybenzaldehyde, has been studied for its utility in chemical analysis. A method for the determination of similar compounds, like 3-bromo-4-hydroxybenzaldehyde, by gas chromatography has been developed, providing a fast, accurate, and precise means of analysis with a high recovery rate (Shi Jie, 2000).

Environmental and Material Sciences

In environmental science, these compounds are utilized in the preconcentration of trace elements. A study demonstrated the use of a Schiff base ionophore, derived from a similar compound (5-bromo-2-hydroxybenzaldehyde), for enriching trace amounts of copper(II) ions in water samples. This method involves using modified octadecyl silica disks for extraction, showcasing an innovative approach to trace element analysis (S. Fathi & M. Yaftian, 2009).

Surface Science and Material Modification

In the field of surface science, 5-bromo-2-hydroxybenzaldehyde has been used to study reactions with monomolecular layers of silanes immobilized on aluminum oxide surfaces. This research aids in understanding the surface chemistry relevant to material sciences and nanotechnology (P. V. Velzen, 1984).

Synthetic Chemistry

5-Bromo-3-fluoro-2-hydroxybenzaldehyde and its derivatives find significant use in synthetic chemistry. For example, a study detailed the synthesis of 5-bromo-3-tert-butyl-2-hydroxy-benzaldehyde, exploring various reaction conditions and confirming structures through 1H-NMR characterization. This showcases its role in creating complex organic compounds (Du Longchao, 2013).

Biochemical Applications

In biochemical research, compounds like 5-bromo-2-hydroxybenzaldehyde have been used in the synthesis of thiosemicarbazone compounds, which have shown potential in DNA interaction studies and antiproliferative activity against cancer cell lines. This underlines its potential in drug discovery and molecular biology (M. A. Hussein & T. S. Guan, 2015).

Safety And Hazards

When handling 5-Bromo-3-fluoro-2-hydroxybenzaldehyde, it is recommended to wear personal protective equipment/face protection. Ensure adequate ventilation. Do not get in eyes, on skin, or on clothing. Avoid ingestion and inhalation. Avoid dust formation.

Future Directions

The compound has potential applications in the synthesis of Schiff base, a sub-class of imine (ketimines or aldimines). It can also be used in the formation of Dy–HOFs.

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