99329-85-8 | 2-Chloro-4-fluoro-5-nitrobenzaldehyde

CAS:99329-85-8 | 2-Chloro-4-fluoro-5-nitrobenzaldehyde,Description

2-Chloro-4-fluoro-5-nitrobenzaldehyde is an important organic intermediate used for synthesizing medicines and pesticides. It is a white or light yellow crystalline solid.

Synthesis Analysis

The synthesis of 2-Chloro-4-fluoro-5-nitrobenzaldehyde involves several steps. The process starts with a nitration reaction on 2-chloro-4-fluorotoluene, followed by a bromination reaction in the presence of benzoyl peroxide. The final step involves a hydrolysis and oxidation reaction to obtain the product.

Molecular Structure Analysis

The molecular formula of 2-Chloro-4-fluoro-5-nitrobenzaldehyde is C7H3ClFNO3. It has a molecular weight of 203.56.

Chemical Reactions Analysis

The compound can undergo various reactions. For instance, it can react with an aldehyde, isonitrile, and a primary amine tethered to a Boc-protected internal amino or hydroxyl nucleophile.

Physical And Chemical Properties Analysis

2-Chloro-4-fluoro-5-nitrobenzaldehyde is a solid at room temperature. It has a density of 1.6±0.1 g/cm3 and a boiling point of 303.6±42.0 °C at 760 mmHg. It is soluble in common organic solvents such as ethanol, methanol, and dimethylformamide.

Scientific Research Applications

Synthesis of 2-Aminobenzylidene Derivatives

2-Chloro-4-fluoro-5-nitrobenzaldehyde is utilized in the stereoselective synthesis of 2-aminobenzylidene derivatives. This process involves a one-pot, three-component approach combining 2-chloro-4-fluoro-5-nitrobenzaldehyde with active methylidene compounds and secondary cycloamines. The method is notable for its high stereoselectivity and yields ranging from 52–88% (Xu et al., 2014).

Theoretical Studies in Organic Chemistry

This compound has been the subject of theoretical studies, such as those involving density functional theory. These studies focus on the internal rotational barriers of nitro groups in molecules like 2-Chloro-4-fluoro-5-nitrobenzaldehyde, offering insights into molecular geometries and electronic properties (Chen & Chieh, 2002).

Heterocyclic Oriented Synthesis

4-Chloro-2-fluoro-5-nitrobenzoic acid, closely related to 2-Chloro-4-fluoro-5-nitrobenzaldehyde, serves as a multireactive building block in heterocyclic oriented synthesis (HOS). This process leads to the preparation of various nitrogenous heterocycles, important in current drug discovery (Křupková et al., 2013) .

Synthesis of Radiopharmaceuticals

Another application is in the synthesis of radiopharmaceuticals for positron emission tomography. Derivatives of 2-Chloro-4-fluoro-5-nitrobenzaldehyde are used as precursors in creating radiopharmaceutical agents, highlighting its significance in medical imaging technologies (Orlovskaja et al., 2016).

Antibacterial Activities

Hydrazone compounds derived from 2-Chloro-4-fluoro-5-nitrobenzaldehyde have been studied for their antibacterial activities. These studies are crucial in exploring new antibacterial materials and understanding their efficacy against various bacterial strains (He & Xue, 2021).

Bioconversion in Fungal Strains

This compound has also been investigated in the context of bioconversion using fungal strains. The bioconversion of aromatic methyl groups to aldehyde groups using laccase from fungal strains is an important application in organic synthesis (Chaurasia et al., 2014).

Safety And Hazards

The compound is classified as a warning hazard. It may cause skin irritation, serious eye irritation, and may cause respiratory irritation.

Future Directions

As an important organic intermediate, 2-Chloro-4-fluoro-5-nitrobenzaldehyde has potential applications in the synthesis of medicines and pesticides. Its future directions will likely be influenced by the demand for these products and advancements in synthetic methods.

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