2-Ethyl-6-methylphenol: Properties, Uses & Safety Guide

2-Ethyl-6-methylphenol is a disubstituted phenolic compound widely used as a chemical intermediate and reference standard in organic synthesis, analytical chemistry, and flavor-fragrance research.

CAS Number

1687-61-2

Molecular Formula

C₉H₁₂O

Molecular Weight

136.19 g/mol

Appearance

Colorless to pale yellow liquid

Aladdin SKU

E156227B

Functional Class

Alkylphenol / Phenolic intermediate

Chemical Identity and Physical Properties

2-Ethyl-6-methylphenol (CAS 1687-61-2) belongs to the family of ortho-disubstituted phenols. Its molecular formula is C₉H₁₂O and molecular weight is 136.19 g/mol. The compound features an ethyl substituent at the 2-position and a methyl substituent at the 6-position of the phenol ring, making both substituents flanking the hydroxyl group in ortho positions.

The compound is typically observed as a colorless to pale yellow liquid at room temperature. The steric bulk introduced by the two ortho substituents influences its reactivity compared to unsubstituted phenol, reducing the nucleophilicity of the oxygen and affecting hydrogen-bonding capacity. These structural features are relevant when selecting it as a building block or analytical reference standard.

Note: Specific boiling point, melting point, density, and refractive index values should be verified against the current Aladdin product specification sheet for lot-specific data.

Synthesis and Preparation Routes

Ortho-alkylated phenols such as 2-ethyl-6-methylphenol are generally accessible via several established routes in organic chemistry:

• Friedel-Crafts alkylation: Alkylation of cresols or phenol with appropriate alkyl halides or olefins in the presence of a Lewis acid catalyst can introduce alkyl groups at ortho positions, though regioselectivity must be carefully controlled.
• Catalytic alkylation: Vapor-phase alkylation of phenols over acidic heterogeneous catalysts (e.g., alumina or zeolites) using alcohols as alkylating agents is an industrially relevant approach that can favor ortho-selectivity.
• Starting from o-cresol or 2-ethylphenol: Further functionalization of mono-substituted phenols provides a more directed route to the disubstituted product.

The specific synthetic route used for Aladdin's E156227B product should be confirmed with the supplier's technical documentation. Researchers synthesizing analogues should consult primary literature for optimized conditions and selectivity data.

Laboratory Applications and Research Uses

2-Ethyl-6-methylphenol serves multiple roles in research and industrial chemistry contexts:

• Organic synthesis intermediate: The phenolic hydroxyl group can participate in etherification, esterification, and coupling reactions, making 2-ethyl-6-methylphenol a versatile building block for more complex molecules including pharmaceuticals, agrochemicals, and specialty polymers.
• Analytical reference standard: The compound may be employed as a certified or in-house reference standard in gas chromatography (GC) and GC-MS analyses, particularly when characterizing phenolic profiles in environmental samples, food matrices, or combustion products.
• Flavor and fragrance research: Certain alkylphenols are associated with characteristic woody, smoky, or spicy odor notes. 2-Ethyl-6-methylphenol may be used in sensory or analytical studies investigating phenolic volatile compounds.
• Physicochemical studies: As a structurally defined phenol derivative, it serves as a model compound for studying steric effects on hydrogen bonding, pKa determination, and reaction kinetics of hindered phenols.

Researchers should confirm suitability of purity grade (available from Aladdin as SKU E156227B) for their specific application prior to use.

Safety, Handling, and Storage

As a phenolic compound, 2-ethyl-6-methylphenol requires standard laboratory precautions associated with handling alkylphenols:

• Personal protective equipment (PPE): Wear appropriate chemical-resistant gloves, safety glasses or goggles, and a laboratory coat. Where vapors may be generated, use in a well-ventilated fume hood.
• Skin and eye contact: Phenolic compounds can cause skin irritation and are potentially corrosive to mucous membranes. Rinse affected areas thoroughly with water if contact occurs and seek medical attention as appropriate.
• Inhalation: Avoid breathing vapors or mists. The compound should be handled in ventilated areas.
• Storage: Store in a tightly sealed container in a cool, dry, well-ventilated location away from strong oxidizing agents and sources of ignition. Refrigerated storage may be appropriate to maintain stability.
• Disposal: Dispose of waste material according to local environmental regulations governing phenolic compounds.

Important: Always consult the current Safety Data Sheet (SDS) provided by Aladdin Scientific for lot-specific hazard information, GHS classification, first-aid measures, and regulatory compliance data before working with this compound.

Purity, Grades, and Quality Considerations

Aladdin Scientific offers 2-ethyl-6-methylphenol under SKU E156227B. When selecting a reagent grade for research, consider the following:

• Purity specification: Confirm the stated purity percentage from the current Aladdin certificate of analysis (CoA) for your specific lot. Higher purity grades are recommended for quantitative analytical work and reference standard applications.
• Analytical methods: Purity is typically assessed by GC or HPLC. Verify that the analytical method reported on the CoA is appropriate for your application requirements.
• Lot-to-lot consistency: For long-term studies or method validation work, document the lot number used to ensure reproducibility across experimental runs.
• Supplier documentation: Request the SDS, CoA, and any available spectral data (NMR, IR, MS) from Aladdin Scientific to support characterization and regulatory compliance needs.

Researchers uncertain about grade suitability should contact Aladdin Scientific's technical support team for guidance specific to their application.

Frequently asked questions

What is the CAS number for 2-Ethyl-6-methylphenol?

The CAS registry number for 2-Ethyl-6-methylphenol is 1687-61-2. This number uniquely identifies the compound and can be used when searching supplier databases, safety data sheets, and chemical literature.

What purity grade of 2-Ethyl-6-methylphenol (E156227B) does Aladdin Scientific offer?

Aladdin Scientific offers 2-Ethyl-6-methylphenol under SKU E156227B. For the exact purity specification and lot-specific data, please refer to the current certificate of analysis (CoA) available on the Aladdin Scientific website or contact the technical support team directly.

What are the main laboratory uses of 2-Ethyl-6-methylphenol?

2-Ethyl-6-methylphenol is primarily used as an organic synthesis intermediate, an analytical reference standard in GC and GC-MS analysis, and a model compound for studying steric effects in hindered phenols. It may also appear in flavor and fragrance research as a representative alkylphenol volatile.

How should 2-Ethyl-6-methylphenol be stored to maintain stability?

Store 2-Ethyl-6-methylphenol in a tightly sealed container in a cool, dry, and well-ventilated area, away from strong oxidizing agents and ignition sources. Refrigerated storage conditions may help maintain long-term stability. Always refer to the current SDS for storage requirements specific to your lot.

Is 2-Ethyl-6-methylphenol hazardous, and what precautions should I take?

As a phenolic compound, 2-Ethyl-6-methylphenol may cause skin and eye irritation and should be handled with appropriate PPE including chemical-resistant gloves and safety goggles. Work in a well-ventilated fume hood to avoid inhalation of vapors. Consult the Aladdin Scientific SDS for complete GHS hazard classification and first-aid procedures before use.

References

1. Aladdin Scientific product page for 2-Ethyl-6-methylphenol, SKU E156227B. Certificate of Analysis and Safety Data Sheet available from Aladdin Scientific upon request.
2. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. (General reference for Friedel-Crafts alkylation and phenol chemistry.)
3. NIST WebBook: 2-Ethyl-6-methylphenol (CAS 1687-61-2). National Institute of Standards and Technology. https://webbook.nist.gov

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.