552331-15-4 | 1-(5-Bromo-2-fluorophenyl)ethanol

CAS:552331-15-4 | 1-(5-Bromo-2-fluorophenyl)ethanol,Description

“1-(5-Bromo-2-fluorophenyl)ethanol” is a chemical compound with the molecular formula C₈H₈BrFO. It has a molecular weight of 219.05 g/mol. The compound is used for research purposes.

Synthesis Analysis

The synthesis of “1-(5-Bromo-2-fluorophenyl)ethanol” involves heating a solution of 1-(5-bromo-2-fluoro phenyl)ethan-1-ol in 1,4-dioxane under a nitrogen atmosphere for 16 hours. The reaction involves the use of MnO2.

Molecular Structure Analysis

The InChI code for “1-(5-Bromo-2-fluorophenyl)ethanol” is 1S/C8H8BrFO/c1-5(11)7-4-6(9)2-3-8(7)10/h2-5,11H,1H3. The structure of the compound has been confirmed by various methods including 1H NMR, 13C NMR, MS, FT-IR, and single crystal X-ray diffraction.

Physical And Chemical Properties Analysis

“1-(5-Bromo-2-fluorophenyl)ethanol” is a liquid at room temperature. It has a boiling point of 254°C at 760 mmHg. The compound is sealed in dry and stored at room temperature.

Scientific Research Applications

Enantioselective Microbial Reduction

1-(5-Bromo-2-fluorophenyl)ethanol serves as a chiral intermediate in the synthesis of various compounds. A significant application is its preparation through enantioselective microbial reduction of acetophenones. This process involves organisms from the genus Candida, Hansenula, Pichia, Rhodotorula, Saccharomyces, Sphingomonas, and Baker's yeast. These organisms reduce acetophenone to 1-(5-Bromo-2-fluorophenyl)ethanol with high yield and enantiomeric excess. This method is notable for its high efficiency and selectivity, making it valuable in pharmaceutical and chemical synthesis (Patel et al., 2004).

X-Ray Crystal Structures Analysis

X-Ray crystallography has been used to analyze the structure of derivatives of 1-(5-Bromo-2-fluorophenyl)ethanol. This technique provides insights into the molecular structure and bonding, which is critical for understanding the compound's physical and chemical properties. The analysis of these crystal structures aids in the development of new compounds with specific desired properties (Percino et al., 2008).

Enantioselective Synthesis Applications

The enantioselective synthesis of 1-(5-Bromo-2-fluorophenyl)ethanol and its analogs is crucial for studying the role of substituents in the chiral recognition of molecular complexes. This has applications in the development of antimalarial drugs and treatments for Alzheimer's disease. The synthesis process often involves bioreduction and optimization techniques to achieve high yield and enantiomeric purity (2022).

Conformational Landscape Study

The conformational landscape of 1-(5-Bromo-2-fluorophenyl)ethanol and its hydrated clusters has been studied using spectroscopic techniques. These studies are important for understanding the compound's behavior under different conditions, which can influence its reactivity and stability. Such information is valuable for applications in material science and pharmaceutical development (Speranza et al., 2009).

Safety And Hazards

The compound is labeled with the signal word “Warning” and has hazard statements H302, H315, H319, H332, and H335. These statements indicate that the compound can cause skin irritation, serious eye irritation, and may cause respiratory irritation. Precautionary measures include avoiding breathing dust/fume/gas/mist/vapors/spray and using only outdoors or in a well-ventilated area.

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