1250921-20-0 | 3-Fluoro-2-(methylamino)benzoic acid

CAS:1250921-20-0 | 3-Fluoro-2-(methylamino)benzoic acid,Description

3-Fluoro-2-(methylamino)benzoic acid is a fluorinated benzoic acid building block used as a synthesis intermediate for APIs and liquid crystals. It is an aryl fluorinated building block. It is also an important compound during the synthesis of Dabrafenib, a type of kinase inhibitor commonly prescribed to individuals suffering from certain forms of melanoma, non-small cell lung cancer, and thyroid cancer.

Synthesis Analysis

The synthesis of 3-Fluoro-2-(methylamino)benzoic acid involves several steps. The process starts from o-methylphenol, carrying out nitration reaction to selectively generate a key intermediate 2-methyl-6-nitrophenol. This is followed by hydroxyl chlorination to generate 2-chloro-3-nitrotoluene, then carrying out fluorination reaction to generate 2-fluoro-3-nitrotoluene, and finally oxidizing methyl under the action of an oxidant to generate 2-fluoro-3-nitrobenzoic acid.

Molecular Structure Analysis

The molecular formula of 3-Fluoro-2-(methylamino)benzoic acid is C8H8FNO2. It has a molecular weight of 169.153.

Physical And Chemical Properties Analysis

3-Fluoro-2-(methylamino)benzoic acid has a density of 1.3±0.1 g/cm3. It has a boiling point of 301.8±32.0 °C at 760 mmHg. The flash point is 136.3±25.1 °C. The exact mass is 169.053909. The LogP value is 2.65. The vapour pressure is 0.0±0.7 mmHg at 25°C. The index of refraction is 1.597.

Scientific Research Applications

Sensor Technology

3-Fluoro-2-(methylamino)benzoic acid has been utilized in sensor technology. A study by (Peng et al., 2020) introduced a hybrid xanthene fluorophore-based sensor for cysteine detection, demonstrating its application in rapid and convenient cysteine detection in living tissues.

Pharmaceutical Synthesis

It plays a crucial role in pharmaceutical synthesis. (Lall et al., 2012) described the stereoselective synthesis of a compound that is a key intermediate in preparing a fluoroquinolone antibiotic used against respiratory tract infections.

Thermodynamic Properties

In the field of thermochemistry, the thermodynamic properties of halogen-substituted benzoic acids, including derivatives of 3-Fluoro-2-(methylamino)benzoic acid, have been studied. (Zherikova & Verevkin, 2019) evaluated these properties using high-level quantum-chemical methods.

Radiopharmaceutical Synthesis

This compound is significant in the synthesis of radiopharmaceuticals. (Ohkubo et al., 2021) discussed its use in automated radiosynthesis of radiotracers for clinical applications in imaging hypoxia and tau pathology.

Liquid Crystal Research

In liquid crystal research, derivatives of 3-Fluoro-2-(methylamino)benzoic acid have been synthesized and characterized for their thermal behavior and phase characterization. (Begum et al., 2013) synthesized bent-core liquid crystals with a polar fluoro end substituent from a related compound.

Chemical Synthesis and Modification

The compound's derivatives have been used in regioselective nitration studies, as described by (Hurth et al., 2015), demonstrating its versatility in chemical synthesis and modification.

Tumor Imaging

In medical imaging, particularly tumor imaging, derivatives of this compound have been synthesized and evaluated for their potential as PET radioligands for imaging brain tumors. (Yu et al., 2010) and (McConathy et al., 2002) explored this application.

Herbicide Development

The compound has been studied for its role in herbicide development. (Hamprecht et al., 2004) investigated the introduction of fluorine atoms into benzoic acid derivatives to improve herbicidal properties.

Gas Phase Spectroscopy

In spectroscopy, the microwave spectrum of mono-fluoro-benzoic acids, including derivatives of 3-Fluoro-2-(methylamino)benzoic acid, has been measured. (Daly et al., 2015) investigated this for understanding molecular interactions in the gas phase.

Chemical Synthesis Variants

In another chemical synthesis application, (Tagat et al., 2002) detailed the synthesis of mono- and difluoronaphthoic acids, showcasing the compound's versatility in synthesizing structurally diverse compounds.

Medicinal Chemistry

In medicinal chemistry, the compound has been used to create fluoro-containing amino acids as potent HCV NS3 protease inhibitors, as demonstrated by (Hu & Han, 2008).

Cascade Synthesis

A study by (Qureshi & Njardarson, 2022) utilized the compound in an anionic cascade synthesis of benzoate esters, showing its application in complex organic synthesis.

Bacterial Growth Inhibition

The compound has been synthesized and investigated for its effects on bacterial growth inhibition, particularly targeting enzymes involved in bacterial cell wall biosynthesis. (Wang et al., 2016) conducted research in this area.

Ortho-Fluorination in Medicinal Chemistry

In a study by (Wang et al., 2009), the compound was used in ortho-fluorination catalyzed by Pd(OTf)2, highlighting its importance in medicinal chemistry and synthesis.

Metal Complex Synthesis

The compound was employed in the synthesis of metal complexes and coordination polymers, as investigated by (Rad et al., 2016), demonstrating its utility in inorganic chemistry.

Antimycobacterial Agents

It has been modified to synthesize novel ofloxacin derivatives with antimycobacterial properties, as shown in the study by (Dinakaran et al., 2008).

Fluorescent Sensing

The compound's derivative has been used in the selective detection of picric acid, illustrating its application in fluorescent sensing technology. (Nagendran et al., 2017) explored this aspect.

Safety And Hazards

3-Fluoro-2-(methylamino)benzoic acid is classified as a hazardous substance. It is recommended to wear personal protective equipment/face protection, ensure adequate ventilation, avoid getting in eyes, on skin, or on clothing, avoid ingestion and inhalation, and avoid dust formation.

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