1644-82-2 | 2-FLUORO-6-NITROBENZALDEHYDE

CAS:1644-82-2 | 2-FLUORO-6-NITROBENZALDEHYDE,Description

2-Fluoro-6-nitrobenzaldehyde is an organic compound with the molecular formula C7H4FNO3 and a molecular weight of 169.11. It is used as a building block in organic chemistry.

Synthesis Analysis

The synthesis of 2-Fluoro-6-nitrobenzaldehyde involves heating a mixture of l-fluoro-2-methyl-3-nitrobenzene and Λ/,Λ/-dimethylformamide dimethyl acetal at 135°C for 12 hours. The reaction mixture is then cooled to room temperature and added dropwise to a solution of sodium periodate in water/DMF. After stirring at room temperature for 3 hours, the mixture is filtered, and the solid is washed with toluene.

Molecular Structure Analysis

The molecular structure of 2-Fluoro-6-nitrobenzaldehyde consists of a benzene ring substituted with a fluoro group at the 2-position and a nitro group at the 6-position.

Chemical Reactions Analysis

While specific chemical reactions involving 2-Fluoro-6-nitrobenzaldehyde are not mentioned in the search results, it is known to be used as an intermediate in organic synthesis.

Physical And Chemical Properties Analysis

2-Fluoro-6-nitrobenzaldehyde is a solid at room temperature. It has a high GI absorption and is BBB permeant. It is soluble in water.

Scientific Research Applications

Radiopharmaceutical Synthesis

2-Fluoro-6-nitrobenzaldehyde has been utilized in the synthesis of radiopharmaceuticals. It serves as a precursor in the preparation of fluorine-18 labeled catecholamines and 6-[18F]fluoro-L-DOPA, which are significant in positron emission tomography (PET) imaging. The fluorination process is carried out under specific conditions to achieve high radiofluorination yields, making these compounds vital in PET scan studies for various medical applications (Orlovskaja et al., 2016).

Molecular Structure and Rotational Barrier Studies

The compound has also been a subject in theoretical studies, particularly in analyzing the molecular geometries and internal rotational barriers of the nitro group. These studies provide insights into the molecular behavior of 2-Fluoro-6-nitrobenzaldehyde and similar compounds, which is crucial in understanding their chemical properties and potential applications (Chen & Chieh, 2002).

Synthesis of Organic Compounds

In organic chemistry, this compound is used in the synthesis of various organic structures. For example, it reacts with arylamines to produce mixtures of 2-arylamino-5-nitrobenzaldehydes, which are further processed to create 2-nitro-acridines, highlighting its role in complex organic synthesis processes (Rosewear & Wilshire, 1981).

Actinometry in Photochemistry

2-Fluoro-6-nitrobenzaldehyde has been explored as a chemical actinometer, useful in measuring the quantum yields of photoreactions. Its stable photochemical properties make it an excellent candidate for actinometric studies in both solution and ice photochemistry, aiding in the understanding of photoreaction mechanisms (Galbavy et al., 2010).

Cyclocondensation Reactions

It has also been investigated in cyclocondensation reactions with amidines. This research has led to a new route for synthesizing 3-aminoisoquinolines, demonstrating the compound's versatility in facilitating diverse chemical reactions (Dar'in et al., 2004).

Synthesis of 2-Aminobenzylidene Derivatives

The compound is involved in the synthesis of 2-aminobenzylidene derivatives, showcasing its utility in creating complex molecules under mild conditions. This synthesis is crucial for the development of new chemical entities with potential applications in various fields (Xu et al., 2014).

Safety And Hazards

2-Fluoro-6-nitrobenzaldehyde is classified as a warning hazard. It may cause harm if swallowed or inhaled, and may cause eye, skin, and respiratory irritation. Precautionary measures include avoiding dust formation, avoiding contact with skin and eyes, and ensuring adequate ventilation.

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