2252-51-9 | 2-Chloro-4-fluorobenzoic acid

CAS:2252-51-9 | 2-Chloro-4-fluorobenzoic acid,Description

Synthesis Analysis

2-Chloro-4-fluorobenzoic acid can be synthesized from m-chloroaniline. The method comprises the following steps: realizing amino protection through 2-(trimethylsilyl)ethoxymethyl chloride; realizing formylation through a Vilsmeier-Haack reaction; oxidizing to obtain carboxylic acid; performing hydrogenation reduction of nitro; and performing a fluorination reaction to obtain 2-chloro-4-fluorobenzoic acid.

Molecular Structure Analysis

The molecular formula of 2-Chloro-4-fluorobenzoic acid is C7H4ClFO2. Its average mass is 174.557 Da and its monoisotopic mass is 173.988388 Da.

Chemical Reactions Analysis

2-Chloro-4-fluorobenzoic acid has been used in the preparation of 2-(2-chloro-4-fluorophenyl)-benzothiazole. It has also been reported to form hydrogen bonded complexes with benzoylhydrazine-based azobenzene compound.

Physical And Chemical Properties Analysis

2-Chloro-4-fluorobenzoic acid is a solid substance. It has a melting point of 181-183 °C. It is soluble in 95% ethanol at a concentration of 50 mg/mL.

Scientific Research Applications

1. Charge Density Analysis in Molecular Crystals

2-Chloro-4-fluorobenzoic acid has been utilized in experimental charge density distribution studies. High-resolution X-ray diffraction data collected at 100 K revealed short Cl···F interactions in 2-chloro-4-fluorobenzoic acid. This study enhances understanding of intermolecular interactions in molecular crystals, particularly the nature of Cl···F interactions (Hathwar & Row, 2011) .

2. Synthesis of Fluazolate

The synthesis of fluazolate, an organic compound, involves 2-chloro-4-fluorobenzoic acid as a starting material. This compound is key in regioselective [3+2] cyclocondensation and nucleophilic substitution-cyclization strategies, demonstrating its utility in complex organic synthesis processes (Hsieh, Lin, & Kuo, 2016).

3. Building Block for Solid-Phase Synthesis

4-Chloro-2-fluoro-5-nitrobenzoic acid, a closely related compound, serves as a multireactive building block for the preparation of substituted nitrogenous heterocycles, highlighting the potential of halogenated benzoic acids in heterocyclic oriented synthesis (Křupková, Funk, Soural, & Hlaváč, 2013) .

4. Vibrational Spectra and NLO Analysis

Studies involving 2-chloro-6-fluorobenzoic acid, a variant of 2-chloro-4-fluorobenzoic acid, have been conducted to understand its vibrational spectra, non-linear optical (NLO) properties, and HOMO-LUMO analyses. This research offers insights into the electronic properties and potential applications of such compounds in materials science (Kumar, Arivazhagan, & Thangaraju, 2015).

5. Photochemistry in a Xenon Matrix

2-Chloro-6-fluorobenzoic acid has been analyzed using FTIR spectroscopy in a xenon matrix at low temperatures. This study helps in understanding the photochemical behavior of halogenated benzoic acids under specific conditions (Kuş, 2017) .

6. Degradation by Bacteria

The degradation of compounds related to 2-chloro-4-fluorobenzoic acid, like fluorobiphenyl, by specific bacteria has been studied. This research is significant for understanding biodegradation processes and the environmental impact of such compounds (Murphy, Quirke, & Balogun, 2008).

Safety And Hazards

2-Chloro-4-fluorobenzoic acid is considered hazardous according to the 2012 OSHA Hazard Communication Standard (29 CFR 1910.1200). It is harmful if swallowed, causes skin irritation, causes serious eye irritation, and may cause respiratory irritation. It is recommended to avoid contact with skin and eyes, avoid breathing dust, and not to ingest.

Future Directions

2-Chloro-4-fluorobenzoic acid may be used in the synthesis of furosemide, 4′-chloro-2′-fluoroacetophenone, novel herbicidal isoxazolecarboxamides, and the preparation of potential liquid crystals.

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