213382-40-2 | 4-Bromo-5-fluoro-2-nitro-benzaldehyde

CAS:213382-40-2 | 4-Bromo-5-fluoro-2-nitro-benzaldehyde,Description

4-Bromo-5-fluoro-2-nitrobenzaldehyde is a compound that has not been directly studied in the provided papers. However, related compounds and methodologies that could be relevant to its synthesis and properties have been investigated. For instance, the synthesis of similar brominated and fluorinated benzaldehydes has been reported, which could provide insights into the synthesis of 4-Bromo-5-fluoro-2-nitrobenzaldehyde.

Synthesis Analysis

The synthesis of related compounds involves various methods, including regioselective bromination and lithiation reactions. For example, 4-Bromo-2-nitrobenzaldehyde was synthesized with high regioselectivity by reacting phenyllithium with 2,5-dibromo-1-nitrobenzene in tetrahydrofuran at -105°C, followed by treatment with dimethylformamide. This method could potentially be adapted for the synthesis of 4-Bromo-5-fluoro-2-nitrobenzaldehyde by starting with an appropriately substituted dibromo-nitrobenzene.

Molecular Structure Analysis

The molecular structure of related compounds has been characterized using techniques such as X-ray diffraction and vibrational spectroscopy. For instance, the crystal structure and vibrational spectra of 2-fluoro-4-bromobenzaldehyde were investigated, and the results were supported by computational studies using density functional theory. These studies provide a foundation for understanding the molecular structure of 4-Bromo-5-fluoro-2-nitrobenzaldehyde, which is likely to exhibit similar characteristics due to the presence of bromo and fluoro substituents.

Chemical Reactions Analysis

The chemical reactivity of bromobenzaldehydes has been explored in the context of aromatic hydroxylation, where bromobenzaldehydes were converted to hydroxybenzaldehydes. This indicates that brominated benzaldehydes can undergo further functionalization, which could be relevant for the chemical reactions of 4-Bromo-5-fluoro-2-nitrobenzaldehyde.

Physical and Chemical Properties Analysis

The physical and chemical properties of brominated and fluorinated benzaldehydes, such as solubility, melting point, and reactivity, can be inferred from the studies on similar compounds. For example, the synthesis of methyl 4-bromo-2-methoxybenzoate from 4-bromo-2-fluorotoluene involved several steps, including bromination and hydrolysis, indicating the reactivity of the bromo and fluoro groups under different conditions. These properties are crucial for the practical application of 4-Bromo-5-fluoro-2-nitrobenzaldehyde in various fields, such as medicinal chemistry and agriculture, as suggested by the urease inhibitory activity of a related Schiff base compound.

Scientific Research Applications

Highly Stereoselective Synthesis of 2-Aminobenzylidene Derivatives 4-Bromo-5-fluoro-2-nitrobenzaldehyde is involved in the stereoselective synthesis of 2-aminobenzylidene derivatives. This process uses a one-pot, three-component approach combining 2-halobenzaldehydes with active methylidene compounds and secondary cycloamines. The method results in high stereoselectivity and yields ranging from 52–88% (Xu et al., 2014).

Structure and Bonding Characteristics The molecule (E)-4-Bromo-N′-(2-nitrobenzylidene)benzohydrazide, derived from 4-Bromo-5-fluoro-2-nitrobenzaldehyde, exhibits a distinct structure where the dihedral angle between the two benzene rings is minimal, indicating a nearly planar arrangement. This structure is stabilized through intermolecular N—H⋯O hydrogen bonds forming a chain in the crystal (Zhang et al., 2009) .

Bromination Specificity and Product Diversity The bromination of 2-nitrobenzaldehyde, a related compound, was studied, revealing a complex product profile with various mono- and dibrominated products, including 4-bromo-2-nitrobenzaldehyde. This showcases the chemical's reactivity and the specificity required in bromination reactions (Cummings & Söderberg, 2014).

Potential in Radiofluorination for PET Imaging Fluorine-18 labeled derivatives of 4,5-Bis(butoxy)-2-nitrobenzaldehyde, a similar compound, are synthesized for use as precursors in synthesizing radiopharmaceutical agents for PET imaging. These derivatives highlight the potential of halogenated benzaldehydes in medical imaging technologies (Orlovskaja et al., 2016).

Crystallography and Vibrational Spectroscopy Studies involving 2-fluoro-4-bromobenzaldehyde (a related compound) highlight the precision in molecular structure analysis, integrating X-ray diffraction and vibrational spectroscopy. This analysis is crucial for understanding the structural and electronic properties of such halogenated compounds (Tursun et al., 2015).

Safety And Hazards

The compound is classified under GHS07 for safety. It has hazard statements H315, H319, and H335, indicating that it can cause skin irritation, serious eye irritation, and may cause respiratory irritation. Precautionary measures include avoiding breathing dust/fume/gas/mist/vapors/spray (P261) and wearing protective gloves/protective clothing/eye protection/face protection (P280).

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