1-Phenylethanol
Overview
1-Phenylethanol is an organic compound classified as a secondary alcohol with a phenyl group attached to the chiral carbon center. First synthesized in the late 19th century, it gained industrial importance with the development of asymmetric synthesis techniques. The compound's significance stems from its dual functionality as both a fragrance ingredient and a versatile building block in pharmaceutical manufacturing. Commercial production occurs through two primary routes: catalytic hydrogenation of acetophenone (yielding racemic mixtures) or enzymatic resolution processes that produce single enantiomers. The global market for 1-phenylethanol is estimated at several thousand metric tons annually, with major producers located in China, Europe, and North America.
Physical and Chemical Properties
As a viscous liquid at room temperature, 1-phenylethanol exhibits characteristic physical constants including a density of 1.012 g/cm³ and boiling point of 203-205°C. Its refractive index (1.527-1.531) serves as a key quality control parameter. The compound demonstrates moderate volatility with a vapor pressure of 0.03 mmHg at 20°C. Chemically, it undergoes typical alcohol reactions including esterification, oxidation to acetophenone, and participation in Williamson ether synthesis. The hydroxyl group's reactivity is slightly reduced compared to primary alcohols due to steric hindrance from the phenyl group. Enantiomers show identical physical properties but differ in optical rotation: (R)-(+)-form rotates plane-polarized light +40.5°, while (S)-(−)-form shows −40.5° (neat).
Main Applications
In the fragrance industry, 1-phenylethanol contributes floral (hyacinth-like) notes to perfumes and cosmetic formulations, often used at 1-5% concentrations. Its stability in alkaline conditions makes it preferable to some terpene alcohols. The pharmaceutical sector utilizes enantiomerically pure forms as chiral auxiliaries in asymmetric synthesis, particularly for β-blockers and other cardiovascular drugs. About 60% of commercial production is consumed by pharma applications. Additional uses include serving as a solvent for specialty polymers, a precursor for styrene derivatives, and an intermediate in agrochemical production.
Safety and Storage
Classified as a Category 4 acute toxicity substance (oral LD50 in rats: 400-800 mg/kg), 1-phenylethanol requires standard laboratory precautions including gloves and eye protection. Its flammability necessitates storage away from ignition sources, ideally in flame-proof cabinets with proper grounding. Long-term stability is maintained under inert gas (argon/nitrogen) with added stabilizers like BHT (0.1%) to prevent oxidation. Bulk shipments typically use 200L steel drums or isotanks with UN number 1987 (Alcohols, flammable, toxic). Shelf life exceeds 24 months when stored properly, though periodic purity checks are recommended for sensitive applications.
B2B Procurement Guide
Industrial buyers should specify: 1) Enantiomeric purity requirements (racemic, R, or S form), 2) Minimum chemical purity (typically 98% or 99%), 3) Packaging preferences (drums, totes, or bulk), and 4) Required certifications (GMP, ISO, or USP). Leading manufacturers include BASF, Symrise, and Jiangsu Hengxing Chemical. Sample quantities (100g-1kg) are often available for qualification testing. MOQs for bulk orders typically start at 500kg with lead times of 2-6 weeks depending on specifications. Consider requesting stability data and residual solvent analysis for pharmaceutical-grade material.
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