96789-80-9 | (S)-1-[3-(TRIFLUOROMETHYL)PHENYL]ETHANOL

CAS:96789-80-9 | (S)-1-[3-(TRIFLUOROMETHYL)PHENYL]ETHANOL,Description

“(S)-1-(3-(Trifluoromethyl)phenyl)ethanol” is a chemical compound with the molecular formula C9H9F3O. It is an optically active isomer of 3,5-bis(trifluoromethyl)phenyl ethanol (3,5-BTPE), which has been shown to be versatile in pharmaceutical synthesis.

Synthesis Analysis

A high-efficiency production of (S)-1-(3,5-bis(trifluoromethyl)phenyl)ethanol ((S)-3,5-BTPE) was achieved using Candida tropicalis 104 as a whole-cell catalyst in a natural deep-eutectic solvent (NADES) containing reaction system under microaerobic conditions. The bioreduction of 3,5-bis(trifluoromethyl)acetophenone (BTAP) was performed in PBS buffer (0.2 M, pH 8.0) at 200 rpm and 30 °C.

Molecular Structure Analysis

The molecular structure of “(S)-1-(3-(Trifluoromethyl)phenyl)ethanol” is represented by the formula C9H9F3O.

Chemical Reactions Analysis

The chemical reaction involved in the production of (S)-1-(3,5-bis(trifluoromethyl)phenyl)ethanol is the bioreduction of 3,5-bis(trifluoromethyl)acetophenone (BTAP) under an oxygen-deficient environment.

Scientific Research Applications

Biocatalytic Synthesis

(S)-1-(3-(Trifluoromethyl)phenyl)ethanol has been a focus in biocatalytic synthesis research. The use of recombinant Escherichia coli cells and other microorganisms like Leifsonia xyli and Trichoderma asperellum has been explored for the efficient asymmetric reduction of related ketones to produce (S)-1-(3-(Trifluoromethyl)phenyl)ethanol with high enantiomeric excess. This process has shown potential for scalable production, indicating its significance in the pharmaceutical industry (Chen et al., 2019), (Ouyang et al., 2013), (Li et al., 2013).

Enzymatic Catalysis

Studies have also delved into the enzymatic catalysis involving Burkholderia cenocepacia for the production of (S)-1-(3-(Trifluoromethyl)phenyl)ethanol. This method has been highlighted for its application in the synthesis of aromatic chiral alcohols, useful in pharmaceutical applications (Yu et al., 2018).

Kinetic Resolution

Kinetic resolution of racemic mixtures to isolate (S)-1-(3-(Trifluoromethyl)phenyl)ethanol has been explored using various catalysts. This process is critical for the preparation of enantiomerically pure forms of the compound, which are often required in the synthesis of specific pharmaceutical agents(Xu et al., 2009), (Wang Lian, 2013).

Medium Engineering in Biocatalysis

Innovative approaches in medium engineering, such as using deep eutectic solvents and cyclodextrins, have been studied to enhance the biocatalytic production of (S)-1-(3-(Trifluoromethyl)phenyl)ethanol. These methods aim to increase substrate solubility and yield, demonstrating the versatility of biocatalysis in producing chiral alcohols (Xiong et al., 2021).

Pharmaceutical Intermediate Synthesis

The compound is a key chiral intermediate in synthesizing various pharmaceuticals, such as NK-1 receptor antagonists like aprepitant and fosaprepitant. Its role as a building block in these syntheses emphasizes its importance in drug development and manufacture (Vankawala et al., 2007) , (Asymmetric Bioreduction, 2011).

Safety And Hazards

The safety data sheet for a similar compound, 1-[3-(Trifluoromethyl)phenyl]ethanol, indicates that it is considered hazardous by the 2012 OSHA Hazard Communication Standard (29 CFR 1910.1200). It may cause skin irritation, serious eye irritation, and respiratory irritation.

Future Directions

The high-efficiency production of (S)-1-(3,5-bis(trifluoromethyl)phenyl)ethanol via a whole-cell catalyst in a deep-eutectic solvent-containing micro-aerobic medium system exhibits potential for enhancing the catalytic efficiency of whole-cell-mediated reduction. This strategy provides valuable insight for the development of whole-cell catalysis.

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