(1S)-1-(4-fluorophenyl)ethanol
The compound (1S)-1-(4-fluorophenyl)ethanol is a chiral alcohol with a fluorine atom attached to the phenyl ring. Here’s a breakdown of its structure and properties:
Structure:
- Core structure: It consists of a phenyl ring (benzene) substituted with a fluorine atom at the para position (4-position) and an ethanol group (–CH(OH)CH₃) at the 1-position.
- Chirality: The compound is chiral due to the presence of a stereocenter at the carbon bearing the hydroxyl group (–OH). The (1S) configuration indicates that the compound is the S-enantiomer (based on the Cahn-Ingold-Prelog priority rules).
Chemical Formula:
- Molecular formula: C₈H₉FO
Key Features:
- Fluorine substituent: The fluorine atom at the 4-position of the phenyl ring is an electron-withdrawing group, which can influence the reactivity and electronic properties of the molecule.
- Hydroxyl group: The –OH group makes the molecule an alcohol, capable of hydrogen bonding and participating in reactions typical of alcohols (e.g., oxidation, esterification).
- Chirality: The (1S) configuration is important in biological systems and synthetic chemistry, as enantiomers can have different activities or reactivities.
Applications:
- This compound could be an intermediate in organic synthesis, particularly in the preparation of pharmaceuticals or fine chemicals.
- The presence of fluorine and the chiral center may make it useful in medicinal chemistry, as fluorine is often used to modulate the properties of drug molecules.
Synthesis:
- It can be synthesized by reducing 4-fluoroacetophenone (a ketone) using a chiral reducing agent or catalyst to achieve the desired (1S) enantiomer.
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