399-00-8 | 5-BROMO-4-FLUORO-2-HYDROXY-BENZALDEHYDE

CAS:399-00-8 | 5-BROMO-4-FLUORO-2-HYDROXY-BENZALDEHYDE,Description

Synthesis Analysis

The synthesis of related bromobenzaldehydes has been explored through various methods. For instance, a general method for converting bromobenzaldehydes to hydroxybenzaldehydes involves in situ protection of the aldehyde function, followed by lithium-bromine exchange and reaction with nitrobenzene. Additionally, the synthesis of methyl 4-bromo-2-methoxybenzoate from 4-bromo-2-fluorotoluene, which shares a similar substitution pattern to the title compound, involves bromination and hydrolysis steps. These methods could potentially be adapted for the synthesis of 5-Bromo-4-fluoro-2-hydroxybenzaldehyde.

Molecular Structure Analysis

The molecular structure of bromo-substituted benzaldehydes has been characterized using various spectroscopic techniques and theoretical calculations. For example, the structural and electronic properties of dimethoxybenzaldehydes with bromine substituents have been discussed, with emphasis on the effects of bromine on the molecular structure. A new polymorph of 2-bromo-5-hydroxybenzaldehyde has been reported, showing significant deviation of the Br atom from the benzene ring plane. These studies suggest that the bromo and hydroxy substituents significantly influence the molecular geometry and electronic distribution in the benzaldehyde core.

Chemical Reactions Analysis

The reactivity of bromobenzaldehydes has been investigated in various chemical reactions. For instance, the reaction of 4-bromobenzaldehyde with substituted acetophenones and urea leads to the formation of substituted pyrimidinones or hexahydropyrimidopyrimidinediones. The bromination of hydroxybenzaldehydes has been shown to yield different bromohydroxybenzaldehydes, depending on the reaction conditions. These studies indicate that bromobenzaldehydes are versatile intermediates in organic synthesis, capable of undergoing a range of chemical transformations.

Physical and Chemical Properties Analysis

The physical and chemical properties of bromo-substituted benzaldehydes have been extensively studied. Spectroscopic (FT-IR and FT-Raman) studies, along with NMR analyses, provide insights into the vibrational and electronic properties of these compounds. The effect of bromine substitution on the linear and nonlinear optical properties has also been investigated, showing that bromine atoms can enhance the nonlinear optical susceptibility. The thermodynamic functions of these compounds have been obtained from spectroscopic data, indicating their energetic behavior in different solvent media. These findings are crucial for understanding the stability and reactivity of 5-Bromo-4-fluoro-2-hydroxybenzaldehyde.

Scientific Research Applications

Application 1: Chemosensor Development

• Specific Scientific Field : Coordination Chemistry and Pharmacology.
• Summary of the Application : 5-Bromo-4-fluoro-2-hydroxybenzaldehyde has been used to synthesize a new Schiff base N,N’-Bis(5-Bromosalicylidine)-1,8-diaminonaphthalene (BBSDN) and its Co(II), Ni(II), Cu(II), and Zn(II) complexes. These compounds have been characterized and studied for their potential as chemosensors.
• Methods of Application or Experimental Procedures : The Schiff base was synthesized from 5-bromo-2-hydroxybenzaldehyde and naphthalene-1,8-diamine and then complexed with Co(II), Ni(II), Cu(II), and Zn(II) ions. The compounds were characterized by various spectral studies (IR, UV, 1H NMR, 13C NMR, and EI-Mass) and DFT calculations. Conductance measurements, magnetic study, and metal estimation studies were performed for the complexes to establish the structure. Thermal studies were done to account for the coordination of water molecules.
• Results or Outcomes : The synthesized compounds were screened against fungal and bacterial pathogens and in most cases, the complexes were found to be more active than the Schiff base. The MIC value for copper and zinc complexes against the fungal pathogen Candida albicans are determined as 25 ppm and 10 ppm respectively. The Schiff base was found to be highly selective and sensitive for the detection of Cu(II) ion.

Application 2: Dysprosium Hydrogen-Bonded Organic Frameworks

• Specific Scientific Field : Materials Chemistry.
• Summary of the Application : 5-Bromo-4-fluoro-2-hydroxybenzaldehyde has been used in the synthesis of a series of dysprosium hydrogen-bonded organic frameworks (Dy–HOFs) with high stability and acid stimulus–response luminescence properties.
• Methods of Application or Experimental Procedures : The reaction of 5-bromo-2-hydroxybenzaldehyde with 2,2-dimethylpropane-1,3-diamine and DyCl3·6H2O under room temperature conditions was used to obtain the Dy–HOFs. The Dy–HOFs were immersed in solutions with different pH values (1–13) for 20 days to test their stability.
• Results or Outcomes : The Dy–HOFs maintained a high degree of stability when immersed in solutions with different pH values for 20 days. The solid-state fluorescence of Dy–HOF samples immersed under acidic conditions had a “turn-on” response, and the solid-state fluorescence increased with increased acidity.

Application 3: Antioxidant and Antimicrobial Activity

• Specific Scientific Field : Pharmacology.
• Summary of the Application : 5-Bromo-4-fluoro-2-hydroxybenzaldehyde has been used in the synthesis of Schiff base ligands of 4-(benzyloxy)-2-hydroxybenzaldehyde. These ligands have been studied for their in vitro antioxidant and antimicrobial activity.
• Methods of Application or Experimental Procedures : The details of the experimental procedures are not provided in the search results.
• Results or Outcomes : The results of the antioxidant and antimicrobial activity studies are not provided in the search results.

Safety And Hazards

The compound is associated with several hazard statements, including H302 (Harmful if swallowed), H315 (Causes skin irritation), H319 (Causes serious eye irritation), and H335 (May cause respiratory irritation). The precautionary statements include P261 (Avoid breathing dust/fume/gas/mist/vapors/spray), P305 (IF IN EYES), P338 (Remove contact lenses if present and easy to do – continue rinsing), and P351 (Rinse cautiously with water for several minutes).

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