703-67-3 | 6-Fluoro-1-tetralone

CAS:703-67-3 | 6-Fluoro-1-tetralone,Description

6-Fluoro-1-tetralone, also known by its IUPAC name 6-fluoro-3,4-dihydro-1(2H)-naphthalenone, is a chemical compound with the molecular formula C₁₀H₉FO. It is a colorless or white to pale-brown solid or liquid . This compound belongs to the class of naphthalenone derivatives.

Molecular Structure Analysis

The molecular structure of 6-Fluoro-1-tetralone consists of a naphthalene ring system with a fluorine atom attached at the 6-position. The compound exists as a bicyclic structure with a carbonyl group (C=O) in the ring .

Physical And Chemical Properties Analysis

• Appearance : Colorless or white to pale-brown solid or liquid 

Scientific Research Applications

Inhibitory Effects on Reactive Oxygen Species Production

• Research Context: A study by Katila et al. (2019) explored the inhibitory effects of halogenated 1-tetralone derivatives, including 6-amino-1-tetralone, on reactive oxygen species (ROS) production in macrophages. The introduction of an amino moiety into the 1-tetralone structure significantly increased inhibitory potency.

Biotransformation in Electrochemical Bioreactors

• Research Context: Shin et al. (2001) evaluated the biotransformation of 6-bromo-2-tetralone to 6-bromo-2-tetralol in an electrochemical bioreactor using yeast cells. The study, as detailed in Applied Microbiology and Biotechnology, found that substrate concentration, biomass, and electric potential significantly affected the biotransformation rates and product formation.

Anti-Proliferative Effects on Cancer Cell Lines

• Research Context: Research by de Souza et al. (2021) synthesized α-aryl-α-tetralones and α-fluoro-α-aryl-α-tetralones, evaluating their in vitro anti-proliferative effects against human breast cancer and leukemia cell lines. Some compounds showed promising results, particularly against drug-resistant cancer cells.

Enzyme Engineering for Chiral Synthesis

• Research Context: Li et al. (2021) conducted a study, published in ChemCatChem, on engineering a carbonyl reductase enzyme for improved catalytic performance towards α-tetralone, including halogenated α-tetralones. This research is significant for chiral synthesis applications.

Regiospecific Fluorofunctionalization of Ketones

• Research Context: Stavber et al. (2002) presented a method for direct regiospecific fluorofunctionalization of the u-carbonyl position in ketones, including 1-tetralone derivatives. This process, as reported in Synthesis , enables the transformation of these derivatives into corresponding α-fluoro derivatives.

Intermediate Synthesis for Receptor Antagonists

• Research Context: A study by Teng Da-wei (2013) in "Chemistry & Bioengineering" discussed the synthesis of 6-Iodo-1-tetralone as an important intermediate for the synthesis of 5-HT6 receptor antagonists.

Electrophilic Fluorination Agents

• Research Context: Cahard et al. (2000) developed enantiopure N-fluoro quaternary ammonium salts of cinchona alkaloids as electrophilic fluorinating agents, which exhibited asymmetric induction on fluorination of enolates and silyl enol ethers of 2-methyl-1-tetralone. This research is described in Organic letters.

Antimicrobial Activity

• Research Context: Abdel-Wahab et al. (2014) synthesized a series of 3-(4-fluorophenyl)-benzo[ g ]indazoles derivatives, including reactions with α-tetralone, and evaluated their antimicrobial activity. The details of this research can be found in European Chemical Bulletin.

Antipsychotic Potential

• Research Context: Carro et al. (2014) synthesized α-tetralone and α-tetralol derivatives and evaluated their binding affinities for dopamine and serotonin receptors. These derivatives, including 6-fluorobenzo[d]isoxazol, showed potential as antipsychotic agents, as reported in European journal of medicinal chemistry.

Safety And Hazards

• Precautionary Statements : P261 (Avoid breathing dust/fume/gas/mist/vapors/spray), P273 (Avoid release to the environment), P305+P351+P338 (IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing) .

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