2-Ethylanisole - ≥98% , CAS No.14804-32-1

CAS: 14804-32-1 Cat. No.: E156216 Formula: C₉H₁₂O Molecular Weight: 136.19

GRADE & PURITY ≥98%

Synonyms

MFCD00142909 | Benzene, 1-ethyl-2-methoxy- | DTXSID10163872 | 2-Ethylmethoxybenzene | SCHEMBL12015267 | FT-0612261 | A808726 | 2-Ethylphenol, methyl ether | SCHEMBL5743040 | 2-Ethylanisole | 2-ethyl-anisole | AKOS008948242 | InChI=1/C9H12O/c1-3-8-6-4-5-7-

Storage

Argon charged,Room temperature

Shipped In

Normal

Specifications

Synonyms

MFCD00142909 | Benzene, 1-ethyl-2-methoxy- | DTXSID10163872 | 2-Ethylmethoxybenzene | SCHEMBL12015267 | FT-0612261 | A808726 | 2-Ethylphenol, methyl ether | SCHEMBL5743040 | 2-Ethylanisole | 2-ethyl-anisole | AKOS008948242 | InChI=1/C9H12O/c1-3-8-6-4-5-7-

Specifications & Purity

≥98%

Storage

Argon charged,Room temperature

Shipped In

Normal

Purity

≥98%

Names and Identifiers

Pubchem Sid

488186267

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/488186267

Canonical Smiles

CCC1=CC=CC=C1OC

IUPAC Name

1-ethyl-2-methoxybenzene

InChIKey

NIEHEMAZEULEKB-UHFFFAOYSA-N

INCHI

1S/C9H12O/c1-3-8-6-4-5-7-9(8)10-2/h4-7H,3H2,1-2H3

Isomeric SMILES

CCC1=CC=CC=C1OC

Molecular Weight

136.19

Reaxy-Rn

2354218

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2354218&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Phenol ethers
      • Subclass Anisoles

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Phenol ethers
• Subclass: Anisoles
• Intermediate Tree Nodes: Not available
• Direct Parent: Anisoles
• Alternative Parents: Phenoxy compounds Methoxybenzenes Alkyl aryl ethers Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Phenoxy compound - Methoxybenzene - Anisole - Alkyl aryl ether - Monocyclic benzene moiety - Ether - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Sensitivity: Air Sensitive
• Refractive Index: 1.51
• Flash Point(°C): 61 °C
• Boil Point(°C): 187°C(lit.)
• Molecular Weight: 136.190 g/mol
• XLogP3: 3.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 136.089 Da
• Monoisotopic Mass: 136.089 Da
• Topological Polar Surface Area: 9.200 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 90.700
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

Not applicable. No tested bioassay protocols (e.g., WB, IHC, IF, FC) or analytical application methods are provided for this item. For synthetic protocols involving 2-ethylanisole, see Reaction Conditions and Synthetic Utility sections and consult the primary literature for detailed, substrate-specific procedures.

Biological Roles

This product is intended for research use only (as stated in Product Data). 2-Ethylanisole is a small aromatic ether without known essential biological function.

Literature context (non-clinical, general):

• Simple anisole derivatives can appear as minor constituents in flavor/fragrance compositions and may be encountered in metabolomic studies of volatile organic compounds, but 2-ethylanisole itself has no established endogenous role in organisms.
• Biotransformations: aromatic ethers may undergo oxidative O-demethylation to the corresponding phenols in microbial or hepatic systems; by analogy, 2-ethylanisole could be converted to 2-ethylphenol under oxidative conditions, though specific metabolic pathways and rates are substrate- and species-dependent.
• Environmental fate: hydrophobic with low water solubility; expected to partition to organic phases and undergo slow biodegradation; volatilization from water is limited by low solubility but possible from surfaces.

Note: No medical, diagnostic, or therapeutic use is implied. For any biological experimentation, consult institutional safety guidelines and the SDS for exposure limits and handling practices.

Buffer Applications

Not typically applicable. 2-Ethylanisole is a nonpolar organic liquid and is not used to prepare aqueous buffers or electrophoresis/cell culture buffer systems.

Practical note: If present as a hydrophobic additive in biphasic or extraction workflows, it will partition to the organic phase; choose appropriate aqueous buffers independently (e.g., phosphate, Tris, acetate) based on your biological system.

Green Alternatives

Context: 2-Ethylanisole is typically used as a synthetic intermediate rather than a routine solvent. When it is used as a medium, greener choices may exist depending on the transformation.

Greener considerations (literature-based):

• As a solvent, aromatic ethers are not on most preferred solvent lists due to persistence and aquatic toxicity concerns relative to bio-based ethers.
• Potential alternatives for high-temperature, nonpolar media:

Comparison (general, literature):

• 2-MeTHF: bio-based, good solvency, bp ~80 °C; greener profile but lower thermal window.
• CPME: good balance of stability and reduced peroxide formation; bp ~106 °C; greener than many ethers; still lower bp than 2-ethylanisole.
• Anisole: often ranked as “recommended/usable” in several guides; bp 154 °C; similar chemistry with lower environmental burden than chlorinated aromatics.
• Toluene/Xylenes: commonly used; toluene has better green rankings than many chlorinated solvents but lower bp; xylenes offer bp 138–144 °C.

Trade-offs:

• If the presence of an anisole-like medium is mechanistically important, anisole can substitute in many cases with easier removal.
• For processes requiring >160 °C, consider high-boiling greenish options like dimethyl carbonate under pressure or solvent-free/flow approaches.

Recommendation:

• Use 2-ethylanisole as a reagent where necessary; otherwise evaluate anisole, 2-MeTHF, or CPME for solvent roles and consult solvent selection guides (e.g., GSK/ACS PMI) for EHS scoring.

Pharmaceutical Uses

Item-specific pharmaceutical grade or compendial status: Not specified for this item; refer to CoA/Spec Sheet.

General, non-clinical context:

• 2-Ethylanisole is not a common pharmaceutical excipient. Its primary relevance in pharma R&D would be as a synthetic intermediate or fine chemical building block in the preparation of aryl ether or phenolic derivatives (e.g., via demethylation to 2-ethylphenol, followed by further functionalization).
• In process chemistry, anisole derivatives are sometimes used as reaction media or quench solvents; however, qualification for GMP use requires full impurity profiling, residual solvent assessment, and EHS review specific to the process.

Compliance note:

• No therapeutic claims are made. Any use in regulated manufacturing would require evaluation against applicable pharmacopeial standards (if any apply) and internal specifications.

Physical Properties

Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general data for 2-ethylanisole (for method development and planning only; not product specifications):

• Physical state: colorless, hydrophobic liquid (aromatic ether; literature)
• Boiling point: typically ~188–190 °C at 1 atm (literature)
• Melting point: typically below −40 °C (liquid well below 0 °C; literature)
• Density: ~0.95 g/mL at 20–25 °C (literature)
• Refractive index (nD20): ~1.503–1.507 (literature)
• Vapor pressure: low at ambient temperature relative to lighter aromatics (qualitative; literature)
• Solubility: practically insoluble in water; miscible with most organic solvents (ethers, alcohols, chlorinated solvents, aromatics) (literature)
• LogP (octanol/water): estimated ~2.7–3.0, indicating significant hydrophobicity (literature/est.)
• Dielectric constant: expected in the range ~3.5–4.5 at 20–25 °C, similar to anisole (literature analogy)
• UV characteristics: aromatic π→π* bands in the near-UV; specific UV cutoff not established for HPLC use (literature)

Practical implications:

• High boiling, low polarity aromatic ether useful when elevated temperatures are required without excessive solvent loss.
• Ether oxygen slightly increases polarizability versus ethylbenzene, improving solvency for moderately polar organics compared to purely hydrocarbon aromatics.

Quality & Grades

Item-specific details from Product Data:

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Storage: Room temperature, Argon charged.
• Shipping: Normal.

Interpretation and guidance (general):

• When grade/purity is unspecified, consult the CoA for assay, GC area %, and residual solvent/water content. Aromatic ethers are typically supplied as high-purity liquids; trace non-aromatic impurities and residual anisoles may be limited.
• Argon-charged packaging: indicates headspace inerting to minimize oxidative degradation and moisture ingress. While aryl ethers are more robust than aliphatic ethers, inert headspace helps preserve quality—especially during long storage or elevated temperatures.
• For chromatography or photochemical use, verify UV absorbance profile and impurity cutoffs on the CoA if low-background is critical.
• Stabilizers: None are indicated in the Product Data. If stabilization is relevant to your application, confirm presence/absence of inhibitors with the CoA.

Best practices:

• Upon receipt, record lot number and retain a copy of the CoA.
• If tight specifications are required (e.g., GC ≥99.5%, water ≤X ppm, metals limits), request the current Spec Sheet; do not assume unstated limits.

Reaction & Applications

Manufacturer Applications: Not specified in Product Data.

General research applications (literature guidance):

• Electrophilic aromatic substitution (EAS): The methoxy group strongly activates the ring; regioselective halogenation, nitration, or sulfonation is typically directed to positions ortho/para to –OMe. The existing ethyl at the 2-position biases further substitution toward para and 4-position.
• Directed metalation: ortho-lithiation adjacent to –OMe is feasible under strong base (s-BuLi/TMEDA) at low temperature, enabling subsequent quench with electrophiles (e.g., carbonyls, CO2, halides) to access substituted 2-ethylanisole derivatives.
• Cross-coupling building block: after halogenation (e.g., bromination) of the ring, the aryl bromide can engage in Pd-catalyzed Suzuki, Buchwald–Hartwig, or Kumada couplings to elaborate the scaffold.
• Ether transformations: demethylation (BBr3, AlCl3, HBr/AcOH) yields 2-ethylphenol, a versatile intermediate for further derivatization (esterification, etherification, O-acylation, and as ligand precursor).
• Oxidations/benzylic chemistry: the benzylic position of the ethyl substituent can undergo oxidation (e.g., to ketone or carboxylate via vigorous oxidants) or radical bromination (NBS) to enable further substitutions.
• C–H activation: serves as a substrate in model studies of site-selective C–H functionalization on anisole frameworks, probing directing effects of –OMe vs alkyl substituents.

Practical tips:

• For regioselective EAS, control temperature and reagent strength to avoid over-substitution.
• For lithiation, maintain rigorously anhydrous conditions and quench judiciously to minimize demethylation.

Reaction Conditions

General conditions reported in the literature for transformations of anisole derivatives; adjust to your substrate and scale:

• Electrophilic bromination: Br2 or NBS/acid catalysts in acetic acid or DCM, 0–25 °C to limit polysubstitution; FeBr3 or AlBr3 can increase rates but risk demethylation at elevated temperature.
• Nitration: mixed acid (HNO3/H2SO4) at 0–10 °C for monosubstitution; the 2-ethyl group steers toward para-selectivity due to ortho blockage.
• ortho-Lithiation: s-BuLi (1.0–1.5 equiv) with TMEDA in THF or Et2O at −78 °C, 0.5–2 h, then electrophile quench (e.g., DMF for formylation); strictly anhydrous, inert atmosphere.
• Benzylic bromination of the ethyl group: NBS (1.1–1.5 equiv), AIBN or radical initiator, CCl4 or refluxing C6H6/PhCF3, hν or Δ, to give benzyl bromide derivatives; follow by substitution or oxidation.
• Demethylation to 2-ethylphenol: BBr3 (1–3 equiv) in DCM at −78→0 °C, 1–4 h; or AlCl3/thiols under milder conditions. Workup carefully to manage exotherm and HBr/phenol release.
• Cross-coupling (after aryl halogenation): Pd(PPh3)4 or modern biaryl phosphine ligands in toluene/dioxane at 80–120 °C for Suzuki–Miyaura; bases such as K3PO4 or Cs2CO3.

Yields: highly substrate- and condition-dependent; consult primary literature for specific targets. Always perform small-scale optimization before scale-up.

Safety & Handling

GHS classification, signal word, pictograms, and H-statements: Not specified for this item; refer to SDS.

General safety considerations for 2-ethylanisole (literature-based guidance; not a substitute for the SDS):

• Expected hazards: combustible/flammable liquid and vapor; may cause skin and eye irritation; harmful if inhaled in high concentrations. Aromatic vapors can cause CNS depression at elevated exposures.
• Incompatibilities: strong oxidizing agents (risk of exotherm), strong acids (may promote demethylation under forcing conditions), and strong bases at high temperature (ether cleavage risk in harsh conditions).
• Engineering controls: handle in a fume hood; ensure adequate ventilation to minimize inhalation exposure.
• PPE: safety glasses or splash goggles, lab coat, and appropriate chemical-resistant gloves (e.g., nitrile). Use flame-resistant lab coat where flammables are handled routinely.
• Fire safety: keep away from ignition sources and hot surfaces. Use CO2, dry chemical, or alcohol-resistant foam for extinguishing. Ground/bond containers during transfer to mitigate static discharge.
• First aid (overview):
  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Skin contact: wash with soap and water; remove contaminated clothing.
  • Eye contact: rinse cautiously with water for several minutes; remove contact lenses if present and easy to do; seek medical attention for irritation.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
• Waste: collect as organic flammable waste per institutional and local regulations.

Solvent Selection

Applicability: 2-Ethylanisole is primarily a building block/intermediate but can serve as a high-boiling, low-to-moderately polar aromatic solvent for certain transformations.

General solvent characteristics (literature):

• Polarity: low; slightly higher polarity than ethylbenzene due to the ether oxygen.
• Dielectric constant: estimated ~3.5–4.5 at 20–25 °C.
• Miscibility: immiscible with water; miscible with common organic solvents (aromatics, ethers, ketones, chlorinated solvents, alcohols).
• Boiling point: ~188–190 °C, enabling higher-temperature reactions than toluene or anisole without pressure equipment.

When to choose 2-ethylanisole:

• As a reaction medium when an inert, aromatic, high-boiling environment is beneficial (e.g., thermal rearrangements, high-temperature metal-catalyzed couplings where substrate is itself 2-ethylanisole).
• When solubility of aryl ethers or hydrophobic substrates is limiting in toluene or xylene.

Comparison (literature, qualitative):

• Toluene (bp 111 °C): lower bp, less polar; better for moderate temperatures, easier removal.
• Anisole (bp 154 °C): more common solvent with similar polarity; lower bp than 2-ethylanisole.
• 1,2,4-Trichlorobenzene (bp 214 °C): higher bp but more hazardous/persistent.

Notes:

• For analytical LC applications, 2-ethylanisole is generally not used as a mobile phase; select acetonitrile, methanol, or IPA instead.

Storage & Reconstitution

Item-specific storage/shipping:

• Storage conditions: Room temperature, Argon charged (as provided). Keep container tightly closed under inert gas when not in use.
• Shipped in: Normal.

General handling and stability (literature-based guidance):

• Aryl ethers like 2-ethylanisole are generally stable under ambient conditions and are not prone to peroxide formation to the extent of aliphatic ethers; routine peroxide testing is typically unnecessary but good laboratory practice includes periodic quality checks for long-stored materials.
• Protect from strong oxidizers and prolonged exposure to strong acids/bases, which can induce degradation (e.g., demethylation).
• If transferring to a new container, purge with argon or nitrogen to maintain an inert headspace and minimize oxidative discoloration.

Reconstitution: Not applicable (neat liquid). If dilution is required for use, select a compatible solvent (e.g., hexanes, toluene, THF, DCM, or anisole) based on the application.

Shelf-life: Not specified for this item; refer to CoA/Spec Sheet. Periodic GC assessment can confirm purity during extended storage.

Structure & Identity

Item-specific (from Product Data):

• Product name: 2-Ethylanisole (o-ethylanisole)
• CAS: 14804-32-1
• PubChem CID: 84654
• InChIKey: 239188 (as provided)
• Storage note: Room temperature, Argon charged

Literature/Computed (general identity information; verify against CoA/SDS for this lot):

• Typical molecular formula: C9H12O (literature)
• Typical molecular weight: ~136.19 g/mol (literature)
• Representative SMILES (one of several valid forms): COc1c(cccc1)CC (literature)

Structural features (general chemistry):

• Aromatic ring bearing two ortho substituents: an electron-donating methoxy group (–OCH3) and an ethyl group (–CH2CH3).
• Functional groups: anisole-type aryl methyl ether; simple alkyl substituent (ethyl).
• 2D description: a benzene ring with methoxy at C1 and ethyl at the adjacent ortho position (C2). No stereocenters; planar aromatic core with a weakly polar ether linkage.

Notes:

• The InChIKey provided appears non-standard in length; consult the product CoA or SDS for the definitive identifier associated with this catalog item.

Synthetic Utility

Functional group leverage:

• Aryl methyl ether (–OMe): activates the ring toward EAS; susceptible to demethylation (BBr3, AlCl3, HI/HBr) to give 2-ethylphenol, enabling downstream O-derivatization.
• Ethyl substituent: provides a benzylic site for radical bromination (NBS, AIBN/hν) and oxidation (KMnO4, Cr(VI), or catalytic aerobic systems) to ketone/carboxylate derivatives.

Strategic transformations (literature):

• Regioselective halogenation or nitration directed by –OMe, followed by cross-coupling (Suzuki–Miyaura, Buchwald–Hartwig) to rapidly elaborate substitution patterns on the anisole core.
• ortho-Lithiation adjacent to –OMe (s-BuLi/TMEDA, −78 to −40 °C) to install formyl, carboxyl, or alkyl groups upon electrophile quench, yielding densely substituted o-ethylanisole scaffolds.
• Transition-metal catalysis: C–H activation on anisole rings (Ir, Pd, Ru) exploiting the ether as a directing/anchoring group in selective borylation or olefination protocols.
• Protecting-group relay: temporary retention of –OMe to guide aromatic substitutions, followed by demethylation to phenol and diversification (O-alkylation, O-acylation, urethane formation), or conversion to aryl triflates for cross-coupling.

Synthesis planning tips:

• Evaluate sterics from the ortho ethyl when targeting adjacent substitutions; para positions are typically more accessible.
• Control conditions to avoid undesired O-demethylation during strongly Lewis acidic or high-temperature steps unless intended.

Target Specificity

Not applicable. This product is a small-molecule reagent and does not possess biological target specificity (no antibody/biologic attributes). For selectivity in chemical reactions, refer to Synthetic Utility and Reaction Conditions sections.

Frequently Asked Questions

What is the purity of this product?

This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature under argon. It is supplied under an argon blanket; reseal under inert gas after each use.

How is this product shipped?

This product ships under standard ambient conditions. No temperature-controlled packaging is required.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 14804-32-1, the molecular formula is C9H12O, and the molecular weight is 136.19 g/mol. InChIKey NIEHEMAZEULEKB-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.