149947-15-9 | 2-BROMO-3-FLUOROBENZALDEHYDE

CAS:149947-15-9 | 2-BROMO-3-FLUOROBENZALDEHYDE,Description

Synthesis Analysis

The synthesis of halogenated aromatic compounds, such as 3-Bromo-2-fluorobenzaldehyde, can be achieved through various methods. For instance, the synthesis of 2-bromo-3-fluorobenzonitrile was accomplished via bromodeboronation of aryl boronic acids, demonstrating the generality of halodeboronation in producing aryl bromides and chlorides. Similarly, substituted 2-bromobenzaldehydes were synthesized from benzaldehydes using a palladium-catalyzed ortho-bromination, indicating that such a strategy could potentially be applied to the synthesis of 3-Bromo-2-fluorobenzaldehyde.

Molecular Structure Analysis

The molecular structure of 3-Bromo-2-fluorobenzaldehyde would consist of a benzene ring substituted with a bromine atom at the 3-position, a fluorine atom at the 2-position, and an aldehyde group. The presence of halogens can significantly influence the electronic properties of the molecule due to their electronegativity, which could affect reactivity and interaction with other chemical species.

Chemical Reactions Analysis

The reactivity of halogenated benzaldehydes can be diverse. For example, 2-bromobenzaldehydes have been used in a one-pot allylboration-Heck reaction to synthesize 3-methyleneindan-1-ols, and in a cascade reaction to form 2H-3-nitrothiochromenes. These reactions highlight the potential of 3-Bromo-2-fluorobenzaldehyde to undergo similar transformations, leveraging the reactivity of the aldehyde group and the ortho-bromine substituent.

Physical and Chemical Properties Analysis

While the specific physical and chemical properties of 3-Bromo-2-fluorobenzaldehyde are not detailed in the provided papers, we can infer that the molecule would likely be a solid at room temperature, with a melting point and boiling point that could be determined experimentally. The presence of halogens would affect its polarity, solubility, and density. The reactivity of the aldehyde group would also be an important chemical property, as it could participate in various organic reactions, such as nucleophilic addition or condensation.

Scientific Research Applications

Synthesis and Antimicrobial Applications

3-Bromo-2-fluorobenzaldehyde is used in the synthesis of various chemical compounds with potential antimicrobial activities. For instance, when it is treated with substituted hydroxyacetophenones, it yields chalcones, which can be further processed into compounds like 2-(4-Bromo-2-fluorophenyl)-4H-chromen-4-one and 2-(4-bromo-2-fluorophenyl)-3-chloro-4H-chromen-4-one. These compounds have been tested and shown to possess antimicrobial properties (Jagadhani, Kundalikar, & Karale, 2014).

Analysis in Drug Substance Production

3-Bromo-2-fluorobenzaldehyde has been analyzed in the context of active drug substance production, specifically AMG 369. Its regioisomer impurities significantly impact the purity of both the starting material and the final drug substance, necessitating the development of high-resolution gas chromatography methods for quality control purposes (Shen, Semin, Fang, & Guo, 2016).

Development of Fluorinated Compounds

In another application, 3-Bromo-2-fluorobenzaldehyde has been used in the synthesis of fluorinated 1,5-benzothiazepines and pyrazolines. These compounds were synthesized through a process involving chalcones and were characterized based on their spectral data (Jagadhani, Kundlikar, & Karale, 2015).

Use in Synthesis of Methyl 4-Bromo-2-methoxybenzoate

A process involving 3-Bromo-2-fluorobenzaldehyde led to the synthesis of Methyl 4-Bromo-2-methoxybenzoate, a compound achieved through a series of chemical reactions including bromination and hydrolysis, followed by cyanidation, methoxylation, and esterification (Chen, 2008).

Safety And Hazards

3-Bromo-2-fluorobenzaldehyde is harmful if swallowed and causes skin and serious eye irritation. It may also cause respiratory irritation. Safety measures include avoiding ingestion and inhalation, not getting it in eyes, on skin, or on clothing, and wearing personal protective equipment/face protection.

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