1305322-97-7 | 5-Bromo-3-chloro-2-fluorophenol

CAS:1305322-97-7 | 5-Bromo-3-chloro-2-fluorophenol,Description

5-Bromo-3-chloro-2-fluorophenol is a chemical compound with the molecular formula C6H3BrClFO. It is a solid substance and its molecular weight is 225.44.

Synthesis Analysis

The synthesis of 5-Bromo-3-chloro-2-fluorophenol involves multiple steps. The process includes the use of potassium carbonate in N,N-dimethyl-formamide at 90°C for 5 hours, followed by the use of tris-(dibenzylideneacetone)dipalladium(0), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, and sodium t-butanolate in tetrahydrofuran at 60°C under an inert atmosphere.

Molecular Structure Analysis

The linear formula of 5-Bromo-3-chloro-2-fluorophenol is C6H3BrClFO. The InChI code is 1S/C6H3BrClFO/c7-3-1-4(8)6(9)5(10)2-3/h1-2,10H.

Physical And Chemical Properties Analysis

5-Bromo-3-chloro-2-fluorophenol has a boiling point of 241.5±35.0°C at 760 mmHg. It has a flash point of 99.8°C. The compound is stored in a sealed, dry environment at 2-8°C.

Scientific Research Applications

Chemoselective Functionalization

5-Bromo-3-chloro-2-fluorophenol has been studied for its chemoselective functionalization properties. A study describes the chemoselective functionalization of a similar compound, 5-bromo-2-chloro-3-fluoropyridine, highlighting the potential for selective substitution reactions in compounds with similar structures (Stroup, Szklennik, Forster, & Serrano-Wu, 2007).

Synthesis of Derivatives for Pharmacological Research

The compound plays a role in synthesizing various derivatives for pharmacological research. An example includes the synthesis of new derivatives based on thiophene, with 5-aryl-2-bromo-3-hexylthiophene, demonstrating potential in pharmacological applications due to their haemolytic, biofilm inhibition, and anti-thrombolytic activities (Ikram et al., 2015).

Studies in Molecular Crystals and Liquid Crystals

Research in molecular crystals and liquid crystals has incorporated halogenated bisbenzyl phenols, similar in structure to 5-Bromo-3-chloro-2-fluorophenol, to explore their electrooptical properties and potential applications in creating esters with large nematic ranges (Gray & Kelly, 1981).

Role in Photoreaction Mechanisms

This compound has been investigated for its role in photoreaction mechanisms. A study on a related compound, 4-bromo-2-chloro-6-fluorophenol, examined its behavior under UV-induced photoreaction pathways, shedding light on the photoreaction mechanisms of halogenated phenols (Nanbu, Sekine, & Nakata, 2012).

Use in Chromatography and Enantioseparation

Compounds similar to 5-Bromo-3-chloro-2-fluorophenol are used in chromatography and enantioseparation. Studies on cellulose and amylose derivatives substituted with halogens have shown their effectiveness as chiral stationary phases in high-performance liquid chromatography (HPLC), useful for resolving racemates (Chankvetadze et al., 1997).

Biodegradation Studies

Biodegradation studies have investigated the metabolism of halophenols by fungi, offering insights into the environmental impact and potential bioremediation strategies for compounds like 5-Bromo-3-chloro-2-fluorophenol (Marr, Kremer, Sterner, & Anke, 1996).

Safety And Hazards

The compound is considered hazardous according to the 2012 OSHA Hazard Communication Standard. It can cause skin corrosion or irritation and serious eye damage or eye irritation. Specific target organ toxicity can occur after a single exposure, with the respiratory system being the target organ.

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