929022-76-4 | 2-CHLORO-4-FLUORONICOTINIC ACID

CAS:929022-76-4 | 2-CHLORO-4-FLUORONICOTINIC ACID,Description

2-Chloro-4-fluoronicotinic acid is a heterocyclic aromatic organic compound. It comprises a nicotinic acid ring with a chlorine and a fluorine atom at the 2- and 4- positions, respectively. The molecular formula is C6H3ClFNO2.

Synthesis Analysis

The synthesis of 2-Chloro-4-fluoronicotinic acid involves a solution of LDA and THF combined and cooled to -78°C. 2-Chloro-4-fluoropyridine is then dissolved in THF and added dropwise over 20 minutes. The solution is stirred for 1 hour.

Molecular Structure Analysis

The molecular weight of 2-Chloro-4-fluoronicotinic acid is 175.545 Da. The monoisotopic mass is 174.983627 Da. The InChI key is GXDFQGOVWALHAS-UHFFFAOYSA-N.

Physical And Chemical Properties Analysis

2-Chloro-4-fluoronicotinic acid has a density of 1.6±0.1 g/cm³. The boiling point is 302.1±37.0 °C at 760 mmHg. The vapor pressure is 0.0±0.7 mmHg at 25°C. The enthalpy of vaporization is 57.3±3.0 kJ/mol. The flash point is 136.5±26.5 °C. The index of refraction is 1.563. The molar refractivity is 36.2±0.3 cm³.

Scientific Research Applications

Synthesis of Pharmaceutical Intermediates

2-Chloro-4-fluoronicotinic acid is utilized in the synthesis of key pharmaceutical intermediates. For instance, it is involved in the practical synthesis of 2-[(1H-pyrrolo[2,3-b]pyridine-4-yl)methylamino]-5-fluoronicotinic acid, a compound with significant pharmaceutical applications. This process involves regioselective chlorination and a palladium-catalyzed cyanation/reduction sequence (Wang et al., 2006).

Preparation of Heterocyclic Scaffolds

4-Chloro-2-fluoro-5-nitrobenzoic acid, a closely related compound, serves as a multireactive building block for heterocyclic oriented synthesis (HOS). This facilitates the preparation of various nitrogenous heterocycles, vital in drug discovery (Křupková et al., 2013) .

Biotransformation Studies

Research on 2-Chloronicotinic acid, a derivative of 2-Chloro-4-fluoronicotinic acid, focuses on its transformation by Rhodococcus erythropolis ZJB-09149. This transformation is significant for the synthesis of pesticides and medicines. The study provides insights into the biotransformation pathway and the enzymes involved in this process (Jin et al., 2011).

Fluorometric and Spectroscopic Applications

The fluorescence quenching mechanism of related compounds like 5-chloro-2-methoxyphenylboronic acid and 4-fluoro-2-methoxyphenyl boronic acid has been studied. These investigations are crucial in understanding the photophysical properties of such compounds (Geethanjali et al., 2015).

Studies in Molecular Structure and Interactions

The study of 2-chloro-4-fluorotoluene, a related compound, involves molecular jet Fourier transform microwave spectroscopy and quantum chemistry. This research provides detailed insights into the molecular structure and internal rotation mechanisms, contributing to our understanding of molecular interactions in similar compounds (Nair et al., 2020).

Analytical Chemistry Applications

The use of 2-chloro-6,7-dimethoxy-3-quinolinecarboxaldehyde, a compound related to 2-Chloro-4-fluoronicotinic acid, in pre-column derivatization for HPLC separation of chlorophenols, highlights its role in analytical chemistry. This application is crucial for the determination of specific compounds in pharmaceutical formulations (Gatti et al., 1997).

Safety And Hazards

The safety information for 2-Chloro-4-fluoronicotinic acid includes a GHS07 pictogram. The signal word is "Warning". Hazard statements include H302-H315-H319-H335. Precautionary statements include P261-P305+P351+P338.

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