(R)-()-1-Phenylethanol

2025年1月3日
产品资讯

(R)-()-1-Phenylethanol

(R)-(+)-1-Phenylethanol is a chiral secondary alcohol with the molecular formula C₈H₁₀O. It is characterized by a phenyl group attached to the first carbon of an ethanol chain, with the hydroxyl group (–OH) on the chiral center. The (R) designation indicates its absolute configuration, and the (+) sign denotes its optical activity, meaning it rotates plane-polarized light in a clockwise direction.

Key Features:

  • IUPAC Name: (R)-(+)-1-Phenylethanol
  • CAS Number: 1517-69-7
  • Molecular Weight: 122.16 g/mol
  • Optical Rotation: [α]D = +40° to +44° (neat or in solution)
  • Appearance: Colorless liquid or solid, depending on temperature
  • Odor: Mild, floral, or aromatic

Structure:

The structure consists of a phenyl ring (C₆H₅) attached to a chiral center (carbon 1) bonded to a hydroxyl group (–OH) and a methyl group (–CH₃).

      OH
       |
  Ph–C*–CH₃
       |
      H

(Ph = Phenyl group, C* = Chiral center)

Synthesis:

  1. Asymmetric Reduction: (R)-(+)-1-Phenylethanol can be synthesized via the asymmetric reduction of acetophenone using chiral catalysts or enzymes.
  2. Chiral Resolution: It can also be obtained by resolving racemic 1-phenylethanol using chiral resolving agents.

Applications:

  • Chiral Building Block: Used in organic synthesis to introduce chirality into more complex molecules.
  • Pharmaceuticals: Serves as an intermediate in the synthesis of chiral drugs.
  • Fragrances: Employed in the production of perfumes and flavoring agents due to its mild aromatic properties.
  • Asymmetric Catalysis: Acts as a ligand or precursor in asymmetric catalytic reactions.

Properties:

  • Solubility: Soluble in organic solvents like ethanol, ether, and chloroform; slightly soluble in water.
  • Boiling Point: ~203–205 °C
  • Melting Point: ~20–22 °C (can vary based on purity)

Safety:

  • Handling: Use in a well-ventilated area with appropriate personal protective equipment (PPE).
  • Storage: Store in a cool, dry place away from strong oxidizing agents.

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