391211-97-5 | 2-(2-Fluoro-4-iodoanilino)-3,4-difluorobenzoic Acid

CAS:391211-97-5 | 2-(2-Fluoro-4-iodoanilino)-3,4-difluorobenzoic Acid,Description

The compound 3,4-Difluoro-2-((2-fluoro-4-iodophenyl)amino)benzoic acid is a multifluorinated aromatic compound that is likely to possess unique chemical and physical properties due to the presence of fluorine and iodine atoms. Fluorinated aromatic compounds are known for their applications in pharmaceuticals, agrochemicals, and advanced materials due to their enhanced stability, lipophilicity, and ability to modulate biological activity.

Synthesis Analysis

The synthesis of fluorinated aromatic compounds can be complex due to the challenges associated with selective fluorination. However, methods such as the Jacobsen cyclization have been used to synthesize related fluorinated benzothiazoles, which suggests that similar cyclization methods could potentially be applied to synthesize the compound . Additionally, the use of aqueous hydrofluoric acid in the presence of iodosylbenzene has been reported as a practical method for the fluorination of 1,3-dicarbonyl compounds, which could be relevant for introducing fluorine atoms into the benzoic acid moiety.

Molecular Structure Analysis

The molecular structure of fluorinated aromatic compounds can be significantly influenced by the presence of fluorine atoms. For instance, the structure of flufenamic acid, a related compound, shows that the carboxyl group and the phenyl ring are nearly coplanar, and the presence of fluorine atoms can affect the overall geometry of the molecule. This suggests that the molecular structure of 3,4-Difluoro-2-((2-fluoro-4-iodophenyl)amino)benzoic acid would also be influenced by its fluorine substituents, potentially affecting its reactivity and interactions.

Chemical Reactions Analysis

Fluorinated compounds often exhibit unique reactivity due to the electron-withdrawing nature of fluorine. The presence of multiple fluorine atoms can enhance the acidity of adjacent functional groups, as seen in the high acidity of the fluorophenol moiety in related benzoxazole and benzothiazole compounds. This property could influence the chemical behavior of the carboxylic acid group in 3,4-Difluoro-2-((2-fluoro-4-iodophenyl)amino)benzoic acid, potentially affecting its reactivity in condensation reactions or its ability to form salts and esters.

Physical and Chemical Properties Analysis

The physical and chemical properties of fluorinated aromatic compounds are often characterized by high thermal stability, low moisture absorption, and unique optical properties. For example, soluble fluoro-polyimides derived from related fluorinated aromatic diamines exhibit excellent thermal stability and hygrothermal stability. Additionally, fluorinated compounds can serve as fluorogenic reagents for high-sensitivity chromatographic analysis due to their fluorescent properties. The presence of a cubic phase in a related mesogen suggests that 3,4-Difluoro-2-((2-fluoro-4-iodophenyl)amino)benzoic acid could also exhibit interesting phase behavior and self-assembly properties, which could be explored for material science applications.

Scientific Research Applications

Vasodilator Activity

3,4-Difluoro-2-((2-fluoro-4-iodophenyl)amino)benzoic acid has been studied for its vasodilator activity. It is an activator of soluble guanylyl cyclase (sGC), which is involved in promoting vasodilation in the pulmonary and systemic vascular beds. This activity is enhanced by specific conditions, indicating the potential for therapeutic applications in managing conditions like pulmonary hypertension (Pankey et al., 2011).

Radiotracer Development

The compound has been part of research exploring new radiofluorinated m-tyrosine analogs for imaging central dopaminergic mechanisms. These analogs, including 6-[18F]fluoro-L-m-trosine (6-FMT), have shown promising results in detecting abnormalities in dopaminergic pathways and could be significant for studying neurological conditions like Parkinson's disease (Barrio et al., 1996).

Radiopharmaceutical Development

The compound has also been involved in the development of novel radiopharmaceuticals for tumor imaging. Derivatives like 2-amino-3-[18F]fluoro-2-methylpropanoic acid (FAMP) and 3-[18F]fluoro-2-methyl-2-(methylamino)propanoic acid (N-MeFAMP) have been studied for their potential in detecting intracranial neoplasms using positron emission tomography (PET) (McConathy et al., 2002).

Metabolism Research

Research on the metabolism of related compounds provides insights into the biotransformation and excretion patterns of these chemicals in organisms. Studies have revealed various pathways and metabolites, contributing to a better understanding of the compound's pharmacokinetics and potential toxicities (Schweinsberg et al., 1979).

Environmental Impact and Degradation

Studies on polyfluoroalkyl chemicals, which share structural similarities with 3,4-Difluoro-2-((2-fluoro-4-iodophenyl)amino)benzoic acid, shed light on the environmental impact and degradation pathways of these chemicals. Understanding the environmental fate, biodegradability, and toxic profiles of these chemicals is crucial for assessing risks and developing strategies for mitigation (Liu & Mejia Avendaño, 2013).

Safety And Hazards

The compound is classified as Acute Tox. 4 Oral according to the Globally Harmonized System of Classification and Labelling of Chemicals (GHS), indicating that it may be harmful if swallowed. It should be stored in a dark place, sealed in dry, at room temperature.

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