357405-75-5 | 4-bromo-2,5-difluorobenzaldehyde

CAS:357405-75-5 | 4-bromo-2,5-difluorobenzaldehyde,Description

Synthesis Analysis

The synthesis of related compounds often involves the condensation of 4-bromobenzaldehyde with other aromatic compounds. For instance, Schiff base monomers were synthesized by condensing 4-bromobenzaldehyde with aromatic aminophenols, followed by oxidative polycondensation to form polyphenol derivatives. Another study reported the synthesis of methyl 4-bromo-2-methoxybenzoate starting from 4-bromo-2-fluorotoluene, which involved multiple steps including bromination, hydrolysis, cyanidation, methoxylation, hydrolysis again, and esterification. These methods could potentially be adapted for the synthesis of 4-Bromo-2,5-difluorobenzaldehyde by choosing appropriate starting materials and reaction conditions.

Molecular Structure Analysis

The molecular structure of compounds similar to 4-Bromo-2,5-difluorobenzaldehyde has been investigated using techniques such as X-ray diffraction and vibrational spectroscopy. For example, the crystal structure of 2-fluoro-4-bromobenzaldehyde was determined, revealing an orthorhombic space group and an O-trans conformation. This suggests that the molecular structure of 4-Bromo-2,5-difluorobenzaldehyde could also be characterized using similar techniques to understand its conformation and crystalline properties.

Chemical Reactions Analysis

4-Bromobenzaldehyde and its derivatives undergo various chemical reactions. For instance, it can participate in condensation reactions with urea and substituted acetophenones to form pyrimidin-2-ones or hexahydropyrimido[4,5-d]pyrimidin-2,7-diones. Additionally, selective ortho-bromination of benzaldoximes to synthesize substituted 2-bromobenzaldehydes has been achieved using palladium-catalyzed C-H activation. These reactions highlight the reactivity of the bromo and aldehyde functional groups, which would also be relevant for 4-Bromo-2,5-difluorobenzaldehyde in similar chemical transformations.

Physical and Chemical Properties Analysis

The physical and chemical properties of halogenated benzaldehydes are influenced by the presence of halogen substituents. For example, the introduction of bromine atoms has been shown to affect the thermal, optical, electrochemical, and fluorescent properties of poly(iminophenol)s derived from 4-bromobenzaldehyde. The presence of electron-donating or withdrawing groups can also modulate the electronic properties, as seen in the study of bromine substitution effects on the structure and reactivity of 2,3-dimethoxybenzaldehyde. These insights suggest that 4-Bromo-2,5-difluorobenzaldehyde would exhibit unique physical and chemical properties due to the combined effects of bromine and fluorine atoms on the benzene ring.

Scientific Research Applications

Synthetic Applications in Organic Chemistry

4-Bromo-2,5-difluorobenzaldehyde and its derivatives, such as 2-bromobenzaldehydes, are pivotal in organic synthesis, particularly under palladium-catalyzed conditions. These compounds serve as essential tools for constructing a wide array of compounds with potential biological and medicinal applications (Ghosh & Ray, 2017).

Analytical Chemistry and Detection Methods

In analytical chemistry, derivatives of 4-Bromo-2,5-difluorobenzaldehyde, like 3-bromo-4-hydroxybenzaldehyde, have been studied for their separation and determination using gas chromatography. This method is noted for its simplicity, accuracy, and precision, making it relevant in various analytical applications (Shi Jie, 2000).

Environmental Applications

Certain derivatives, such as bis(5-bromo-2-hydroxybenzaldehyde)-1,2-propanediimine, synthesized from 5-bromo-2-hydroxybenzaldehyde, are used for environmental purposes like the preconcentration of trace amounts of copper(II) ions in water samples. This application is significant for monitoring and managing environmental pollutants (Fathi & Yaftian, 2009).

Pharmaceutical and Biomedical Research

In the pharmaceutical sector, 4-bromo-2,5-difluorobenzaldehyde derivatives are explored for their potential in creating novel compounds with bioactive properties. For instance, the synthesis of N-Piperidine benzamides CCR5 antagonists from related compounds demonstrates the relevance of these derivatives in drug development and biological research (Cheng De-ju, 2015).

Material Science

In material science, derivatives of 4-Bromo-2,5-difluorobenzaldehyde have been used to synthesize various materials. For example, methyl 4-bromo-2-methoxybenzoate, synthesized from related compounds, demonstrates the utility of these aldehydes in creating high-purity materials for various industrial applications (Chen Bing-he, 2008).

Safety And Hazards

4-Bromo-2,5-difluorobenzaldehyde is considered hazardous. It may cause skin burns, eye damage, and respiratory irritation. Safety precautions include wearing suitable personal protective equipment, such as gloves, protective clothing, and eye protection.

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