213382-45-7 | 5-bromo-4-fluoro-2-nitrobenzaldehyde

CAS:213382-45-7 | 5-bromo-4-fluoro-2-nitrobenzaldehyde,Description

5-Bromo-4-fluoro-2-nitrobenzaldehyde is a compound that is not directly discussed in the provided papers. However, the papers do provide insights into related bromo-nitrobenzaldehyde compounds and their properties, which can be used to infer some aspects of the target compound's characteristics. For instance, the synthesis of similar compounds involves the use of bromination and nitration reactions, as well as the manipulation of functional groups to achieve the desired substitution pattern on the benzene ring.

Synthesis Analysis

The synthesis of bromo-nitrobenzaldehyde derivatives typically involves regioselective bromination and nitration reactions. For example, the synthesis of 4-bromo-2-nitrobenzaldehyde is achieved through a reaction of phenyllithium with 2,5-dibromo-1-nitrobenzene, followed by a reaction with dimethylformamide to yield the desired aldehyde with high regioselectivity and yield. Similarly, the synthesis of 5-bromo-2-methoxybenzaldehyde from 4-bromo-2-fluorotoluene involves a series of reactions including bromination, hydrolysis, cyanidation, methoxylation, and esterification. These methods could potentially be adapted for the synthesis of 5-Bromo-4-fluoro-2-nitrobenzaldehyde by choosing appropriate starting materials and reaction conditions.

Molecular Structure Analysis

The molecular structure of bromo-nitrobenzaldehyde derivatives is characterized by the presence of bromine and nitro groups on a benzene ring, which can significantly influence the electronic and steric properties of the molecule. For instance, the Br atom in 2-bromo-5-hydroxybenzaldehyde deviates from the plane of the benzene ring, and the aldehyde group is twisted, indicating that similar deviations and twists could be expected in the structure of 5-Bromo-4-fluoro-2-nitrobenzaldehyde. Additionally, the presence of substituents like fluorine and nitro groups would likely affect the electron density and reactivity of the compound.

Chemical Reactions Analysis

Bromo-nitrobenzaldehyde compounds can participate in various chemical reactions, including condensation to form Schiff bases, as demonstrated by the synthesis of a Schiff base compound from 5-bromo-2-hydroxybenzaldehyde. The nitro group can also be involved in further chemical transformations, such as reduction to an amine. The reactivity of these compounds is influenced by the electron-withdrawing effects of the nitro and bromo substituents, which can activate the benzene ring towards nucleophilic aromatic substitution reactions.

Physical and Chemical Properties Analysis

The physical and chemical properties of bromo-nitrobenzaldehyde derivatives are influenced by their functional groups. For example, the presence of a nitro group can increase the compound's polarity and impact its solubility in various solvents. The spectroscopic properties, such as FT-IR and FT-Raman, can be studied using density functional theory (DFT) to understand the vibrational modes of the molecule. Additionally, the electronic properties, including HOMO and LUMO energies, can be analyzed to predict the chemical reactivity and stability of the compound. The thermodynamic functions, such as heat capacity and Gibbs energy, can be obtained from spectroscopic data to understand the compound's behavior at different temperatures.

Scientific Research Applications

Synthesis of Derivatives

5-Bromo-4-fluoro-2-nitrobenzaldehyde plays a significant role in the synthesis of various chemical compounds. For instance, it is used in the stereoselective synthesis of 2-aminobenzylidene derivatives, which are formed from 5-nitro/cyano-activated 2-halobenzaldehydes through a novel parallel convergent Knoevenagel–nucleophilic aromatic substitution approach. This process is notable for its high stereoselectivity and yields ranging from 52% to 88% (Xu et al., 2014).

Crystallography and Molecular Structure Studies

The compound has been used in the study of molecular structures and crystallography. For example, the synthesis of (E)-4-Bromo-N′-(2-nitrobenzylidene)benzohydrazide involved the use of 2-nitrobenzaldehyde and 4-bromobenzohydrazide, providing insights into molecular configurations and intermolecular hydrogen bonding patterns (Zhang et al., 2009) .

Radiopharmaceutical Synthesis

In the field of radiopharmaceuticals, derivatives of 5-Bromo-4-fluoro-2-nitrobenzaldehyde are utilized as precursors. These precursors, like 4,5-Bis(butoxy)-2-nitrobenzaldehyde, have been synthesized for use in the creation of important radiopharmaceutical agents for positron emission tomography, offering advantages in terms of labile protective groups which can be removed without aggressive chemicals (Orlovskaja et al., 2016).

Safety And Hazards

The compound is classified under GHS07 and has the signal word 'Warning’. The hazard statements associated with it are H302, H315, H319, and H335. The precautionary statements are P261, P305+P351+P338.

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