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Ethyl phenyl ether

Ethyl phenyl ether, commonly known as phenetole or ethoxybenzene, is an organic compound with the molecular formula C₈H₁₀O and the structural formula C₆H₅OC₂H₅, consisting of an ethyl group linked via an oxygen atom to a phenyl ring, classifying it as an aryl alkyl ether.^[1]^[2] It appears as a clear, colorless to slightly yellow liquid with a pleasant, sweet odor, exhibiting typical ether properties such as volatility and the potential to form explosive peroxides upon exposure to air.^[3]^[2] Key physical properties include a boiling point of 169–170 °C at standard pressure, a melting point of -30 °C, a density of 0.966 g/mL at 25 °C, and a flash point of 57 °C (135 °F), rendering it flammable and suitable for applications requiring moderate thermal stability.^[2]^[4] The compound is insoluble in water but freely soluble in alcohols, oils, and other organic solvents, with a refractive index of 1.507 and low vapor pressure that supports its use in controlled environments.^[2]^[3] Phenetole is synthesized industrially via the Williamson ether synthesis, involving the etherification of phenol with ethyl chloride or diethyl sulfate in the presence of a base, a process that highlights its derivation from readily available aromatic precursors.^[2] It serves primarily as a versatile solvent and synthetic intermediate in the production of pharmaceuticals, agrochemicals, fragrances, coatings, adhesives, and polymers, owing to its non-polar nature and chemical stability.^[3] Additionally, it functions as an analyte in analytical assays for materials like porous graphitic carbon.^[5] Safety considerations include its classification as a flammable liquid (H226) that requires storage away from ignition sources and protection from peroxide formation, with precautionary measures emphasizing proper ventilation and handling.^[2]

Identity and nomenclature

Names and synonyms

Ethyl phenyl ether is systematically named ethoxybenzene according to IUPAC nomenclature.^[1] Its common names include phenetole, ethyl phenyl ether, phenyl ethyl ether, and phenetol.^[1] The CAS Registry Number is 103-73-1, and the PubChem CID is 7674; the molecular formula is C₈H₁₀O.^[1] The name phenetole originated in the 19th century, derived from "pheno-" (referring to the phenyl group) and "ethyl," as part of early systematic naming conventions for ethers.^[6] It serves as the ethyl analog of anisole, the corresponding methyl phenyl ether.

Molecular formula and structure

Ethyl phenyl ether has the molecular formula C₈H₁₀O.^[1] Its molar mass is 122.16 g/mol.^[1] The compound features a structural formula of C₆H₅OC₂H₅, consisting of a benzene ring directly bonded to an oxygen atom, which is further connected to an ethyl group (–CH₂CH₃).^[1] This arrangement is depicted in chemical diagrams as a six-membered phenyl ring attached via the oxygen to the two-carbon ethyl chain, emphasizing the asymmetric ether linkage. As an aryl alkyl ether, ethyl phenyl ether contains a characteristic C–O–C ether bond where one oxygen substituent is an sp²-hybridized aromatic phenyl group and the other is an sp³-hybridized alkyl ethyl chain; the phenyl ring's aromaticity imparts enhanced stability compared to simple dialkyl ethers. The molecular geometry includes a planar phenyl ring due to delocalized π-electrons, with the oxygen atom exhibiting sp³ hybridization resulting in a C–O–C bond angle of approximately 118° and tetrahedral-like coordination around the ethyl methylene carbon.

Physical properties

Appearance and phase behavior

Ethyl phenyl ether, commonly known as phenetole, is a colorless oily liquid at room temperature. It exhibits an aromatic, sweet odor characteristic of many aromatic ethers.^[7]^[8] The compound has a melting point of -30 °C, remaining liquid under typical ambient conditions. Its boiling point is 169–170 °C at standard atmospheric pressure (760 mmHg). The density is 0.966 g/cm³ at 25 °C, indicating it is slightly less dense than water.^[9]^[9]^[10]^[4] Phenetole possesses moderate volatility, with a vapor pressure of approximately 1.7 mmHg at 25 °C. Its vapors are heavier than air and can form explosive mixtures with air when heated or in confined spaces.^[11]^[12]

Solubility and thermodynamic data

Ethyl phenyl ether, also known as phenetole, demonstrates limited solubility in water, with a measured value of 569 mg/L (or 0.0569 g/100 mL) at 25 °C, classifying it as practically insoluble under standard conditions. This low aqueous solubility arises from its nonpolar aromatic and alkyl structure, which hinders effective hydrogen bonding with water molecules. In contrast, it exhibits high solubility in a range of organic solvents, including ethanol, diethyl ether, and chloroform, where it readily dissolves due to favorable van der Waals interactions and similar polarity profiles.^[1]^[2] The octanol-water partition coefficient (logP) for ethyl phenyl ether is 2.78 (measured at 23 °C via shake-flask method with liquid scintillation counting), underscoring its lipophilic character and preference for non-aqueous environments over polar ones. This value positions it as moderately hydrophobic, influencing its distribution in biphasic systems relevant to extraction and partitioning studies.^[13] Thermodynamic parameters further characterize its behavior. The enthalpy of vaporization (ΔvapH) at the boiling point of approximately 443 K is 40.7 kJ/mol, reflecting the energy required to overcome intermolecular forces in the liquid phase during vaporization. The flash point, indicative of ignition risk, is 57 °C (closed cup method), highlighting its flammability under moderate heating. Additionally, the refractive index is 1.5076 at 20 °C, a property tied to its electronic structure and density, useful for purity assessment in analytical contexts.^[4]^[1]^[1]

Synthesis

Williamson ether synthesis

The Williamson ether synthesis serves as the primary laboratory method for preparing ethyl phenyl ether through an SN2 reaction between sodium phenoxide and ethyl bromide.^[14] The reaction proceeds as follows:

\mathrm{C_6H_5ONa + CH_3CH_2Br \rightarrow C_6H_5OCH_2CH_3 + NaBr}

^[15] This approach, developed by Alexander Williamson in 1850, was applied to aryl alkyl ethers during the 19th century.^[16] In the mechanism, the phenoxide ion functions as a strong nucleophile, attacking the electrophilic carbon atom of the ethyl bromide in a concerted SN2 displacement, with inversion of configuration and expulsion of the bromide leaving group. The reaction is generally carried out in anhydrous ethanol under reflux to promote efficient substitution while minimizing side reactions.^[17] Yields for this synthesis typically range from 80% to 90% when using primary alkyl halides like ethyl bromide, offering a significant advantage over other methods for constructing aryl alkyl ethers due to the clean SN2 pathway and compatibility with aromatic alkoxides.^[17]

Alternative preparation methods

Ethyl phenyl ether, also known as phenetole, can be prepared by reacting sodium phenoxide with diethyl sulfate in an aqueous alkaline medium, yielding the ether and sodium ethyl sulfate as a byproduct.^[1] The reaction proceeds as follows:

\mathrm{C_6H_5ONa + (CH_3CH_2)_2SO_4 \rightarrow C_6H_5OCH_2CH_3 + CH_3CH_2OSO_3Na}

This method is a classical alternative to alkyl halide-based approaches and is noted for its straightforward execution in basic conditions.^[2] Another route involves the acid-catalyzed condensation of phenol with ethanol under strong acidic conditions, such as with sulfuric acid, at elevated temperatures around 150–200°C, producing ethyl phenyl ether in approximately 61% yield alongside side products like diethyl ether from alcohol dehydration.^[18] This method suffers from low selectivity due to competing C-alkylation and dehydration reactions, limiting its efficiency for pure product isolation.^[19] A copper-catalyzed Ullmann-type coupling provides a variant for synthesizing alkyl aryl ethers, involving the reaction of aryl iodides or bromides with aliphatic alcohols like ethanol in the presence of a copper catalyst, base, and ligand such as N,N-dimethylglycine, typically at 110°C.^[20] While effective for hindered substrates, yields for simple ethyl phenyl ether are moderate (around 50–80% depending on conditions) due to challenges with primary alkyl groups.^[21] On an industrial scale, ethyl phenyl ether is primarily synthesized via the Williamson ether synthesis or the diethyl sulfate method, as its niche applications do not warrant dedicated large-scale production facilities.^[2]

Chemical properties and reactions

Stability and general reactivity

Ethyl phenyl ether, also known as phenetole, demonstrates relative stability under ambient conditions, largely due to the conjugative effect of the aromatic ring, which strengthens the ether linkage and imparts resistance to hydrolysis in neutral or basic environments.^[22]^[23] Unlike dialkyl ethers, which are more susceptible to cleavage, the aryl-alkyl structure in ethyl phenyl ether maintains integrity without significant decomposition during typical storage or handling.^[24] The ether oxygen in ethyl phenyl ether exhibits weak basicity, with protonation being rare owing to the low pKa of its conjugate acid, approximately -2 to -3, which reflects the poor ability of the oxygen lone pairs to stabilize a positive charge.^[25] Regarding oxidative reactivity, ethyl phenyl ether does not form peroxides as readily as aliphatic dialkyl ethers but can develop them upon prolonged exposure to air and light, classifying it among compounds that may pose a peroxide hazard if stored improperly for extended periods.^[1]^[26] Spectroscopic characterization supports its structural stability and ether functionality. In infrared (IR) spectroscopy, ethyl phenyl ether displays a characteristic asymmetric C-O-C stretch at approximately 1250 cm⁻¹ and aromatic C-H stretches around 3000 cm⁻¹, confirming the presence of the aryl-alkyl ether motif.^[27] Proton nuclear magnetic resonance (¹H NMR) reveals the ethyl CH₂ protons as a quartet near 4.0 ppm and the phenyl protons as a multiplet between 6.8 and 7.3 ppm, indicative of the deshielded benzylic methylene and the aromatic ring, respectively.^[28]

Specific reactions and transformations

Ethyl phenyl ether, also known as phenetole, undergoes selective cleavage with strong acids such as HI or HBr, preferentially breaking the alkyl-oxygen bond due to the greater strength of the aryl C-O bond compared to the alkyl C-O bond. This reaction proceeds via protonation of the ether oxygen followed by an SN2 nucleophilic attack by the halide ion on the less hindered ethyl group, yielding phenol and the corresponding alkyl halide. For example, treatment with concentrated HI produces phenol and ethyl iodide, while HBr yields phenol and ethyl bromide.^[29] The ethoxy substituent (-OEt) in ethyl phenyl ether acts as a strong activating and ortho/para-directing group for electrophilic aromatic substitution on the phenyl ring, similar to the alkoxy groups in related ethers. Nitration of phenetole using pernitrous acid results in ortho- and para-nitro derivatives, with the para isomer predominating due to steric factors. Halogenation, such as bromination in aqueous acetic acid, also occurs preferentially at the ortho and para positions, enabling regioselective functionalization of the aromatic ring.^[30]^[31] Ethyl phenyl ether exhibits resistance to mild oxidizing agents, owing to the stabilizing ether linkage that moderates the reactivity of the aromatic ring compared to free phenols.

Applications

Industrial and synthetic uses

Ethyl phenyl ether, also known as phenetole, serves primarily as a chemical intermediate in the synthesis of various industrial compounds. It is utilized in the production of dyes, where it acts as a building block for aromatic derivatives.^[23] In the pharmaceutical sector, phenetole functions as an intermediate in the synthesis of pharmaceuticals.^[23] Additionally, it finds application in the agrochemical industry as an intermediate for agrochemicals.^[3] Due to its low polarity and thermal stability, phenetole is employed as a solvent in organic reactions, facilitating processes like extractions and formulations where non-polar media are required.^[3] Its solubility in common organic solvents such as ethanol and ether enhances its utility in laboratory and small-scale industrial syntheses.^[32] In the fragrance and flavor industries, phenetole contributes its mild aromatic odor as a component in perfume formulations and spice blends, often serving as a precursor for more complex scented compounds.^[1] Phenetole is produced on a small-volume scale, primarily for niche applications rather than as a high-volume commodity chemical.^[1] It also serves as an analyte in analytical assays for materials like porous graphitic carbon and as a model compound in pyrolysis studies simulating lignin degradation in biomass research.^[5]^[33]

Natural occurrence and biological roles

Ethyl phenyl ether, also known as phenetole, has been reported as a natural constituent in the medicinal herb Scutellaria barbata (barbated skullcap), a perennial plant used in traditional Chinese medicine.^[1] It occurs as a minor component in the essential oil of this plant, extracted via hydrodistillation from aerial parts. In S. barbata, ethyl phenyl ether contributes to the overall profile of volatile organic compounds in the essential oil, which exhibits broad-spectrum antimicrobial activity. The oil demonstrated inhibitory effects against Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus, outperforming activity against Gram-negative bacteria and yeasts.^[34]

Safety and environmental considerations

Health and toxicity hazards

Ethyl phenyl ether, also known as phenetole, exhibits low acute toxicity via oral administration, with an LD50 value of 2,200 mg/kg in mice, indicating minimal risk from ingestion in typical exposure scenarios.^[7] Inhalation represents the primary exposure hazard due to its volatile nature, where vapors can cause respiratory irritation; the LC50 for rats is 8,949 mg/m³ in air, suggesting moderate irritant potential rather than severe systemic toxicity.^[7] Dermal exposure shows low acute toxicity, with an LD50 greater than 2,000 mg/kg in rabbits, though direct contact may lead to mild skin and eye irritation.^[7] Chronic effects from prolonged exposure are not well-documented, and phenetole is not classified as a carcinogen by the International Agency for Research on Cancer (IARC).^[35] Regulatory assessments do not list ethyl phenyl ether as a controlled substance, but it is managed as a hazardous material primarily due to its flammability, requiring appropriate labeling and transport protocols under chemical safety standards.^[36]

Handling and storage precautions

Ethyl phenyl ether, a highly flammable liquid with a flash point of 57 °C, requires careful handling to minimize fire risks; operations should be conducted in well-ventilated areas using non-sparking tools and explosion-proof equipment to prevent ignition from static discharge or open flames.^[36] Personnel must wear appropriate personal protective equipment (PPE), including chemical-resistant gloves (such as Viton), safety goggles, flame-retardant clothing, and a vapor respirator if airborne concentrations exceed safe limits, to protect against skin contact, eye exposure, and inhalation.^[37] For storage, containers should be kept tightly sealed in a cool, dry, well-ventilated location away from heat sources, ignition points, and incompatible materials like strong oxidizers; glass or metal containers are suitable due to the compound's compatibility with these materials.^[36] As an ether, it has the potential to form explosive peroxides upon prolonged exposure to air, particularly if distilled or concentrated; to mitigate this, stabilizers may be added, or the material should be tested periodically for peroxide content before use. In the event of a spill, all ignition sources must be eliminated immediately, and the liquid should be absorbed using an inert material such as vermiculite or sand, avoiding dilution with water to prevent spreading the flammable hazard; contaminated absorbents should then be collected in sealed containers for proper disposal.^[36]

Environmental impact

Ethyl phenyl ether is considered to have moderate ecotoxicity. Reported values include an LC50 of 120 mg/L for fish (Leuciscus idus, 48 h), an EC50 of 117 mg/L for Daphnia magna (48 h), and an EC50 of 162 mg/L for the alga Pseudokirchneriella subcapitata (96 h).^[7] It shows biodegradability, with a theoretical biochemical oxygen demand (BOD) of 63% over 2 weeks, and is not classified as persistent, bioaccumulative, and toxic (PBT) or very persistent and very bioaccumulative (vPvB).^[7]^[35] Environmental release should be minimized, and spills prevented from entering drains or waterways.^[36]

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