Overview
(R)-1-Phenylethanol is a chiral secondary alcohol with a phenyl group attached to the chiral center. It is the (R)-enantiomer of 1-phenylethanol, distinguished by its specific optical rotation and stereochemistry. This compound is commercially significant due to its role as a building block in asymmetric synthesis and as a chiral auxiliary in pharmaceutical manufacturing. The compound is synthesized via asymmetric reduction of acetophenone or kinetic resolution of racemic 1-phenylethanol. Its high enantiomeric purity (typically ≥98% ee) makes it valuable for applications requiring strict stereochemical control, such as drug development and fine chemical production.
Physical and Chemical Properties
(R)-1-Phenylethanol is a colorless to pale yellow liquid with a mild, floral odor. It has a density of 1.013 g/cm³ at 20°C and boils at 204-205°C. The compound is soluble in organic solvents like ethanol and ether but has limited solubility in water (approximately 1.6 g/100 mL at 20°C). Its optical rotation ([α]D) is approximately -45° (neat), a key identifier for enantiomeric purity. The compound is stable under normal storage conditions but may oxidize to acetophenone upon prolonged exposure to air. It exhibits typical alcohol reactivity, participating in esterification, etherification, and nucleophilic substitution reactions.
Main Applications
In pharmaceuticals, (R)-1-Phenylethanol serves as an intermediate for chiral drugs, including β-blockers and antihistamines. Its ability to induce stereoselectivity makes it useful in asymmetric catalysis and resolution of racemic mixtures. The compound is also employed as a chiral derivatizing agent for HPLC analysis. In the fragrance industry, it contributes to floral and fruity notes in perfumes and cosmetics. Additionally, it acts as a solvent for resins and cellulose esters in specialty coatings. Recent research explores its potential in green chemistry as a bio-based platform molecule for sustainable synthesis.
Safety and Storage
(R)-1-Phenylethanol is classified as flammable (Flash point: 90°C) and may cause eye/skin irritation upon contact. Use nitrile gloves, safety goggles, and fume hoods when handling. In case of spills, absorb with inert material and dispose of as hazardous waste. Store in tightly sealed amber bottles under nitrogen or argon to prevent oxidation. Ideal storage temperature is 2-8°C for long-term preservation. Compatibility testing is recommended before mixing with strong acids, bases, or oxidizers due to potential exothermic reactions.
B2B Procurement Guide
When sourcing (R)-1-Phenylethanol, prioritize suppliers with ISO 9001 certification and batch-specific Certificates of Analysis (CoA). Key specifications to verify include enantiomeric excess (≥98% ee), chemical purity (≥99%), and residual solvent levels (e.g., <0.1% acetone). Bulk purchases (25kg drums) typically offer 10-15% cost savings compared to small-scale packaging. Request stability data and SDS documentation for regulatory compliance. For international shipments, ensure proper hazardous material labeling (UN 1987, Class 3) and temperature-controlled transport if required.
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