2-Methyl-6-[(E)-2-phenylethenyl]pyridine: Properties & Lab Guide

2-Methyl-6-[(E)-2-phenylethenyl]pyridine is a trans-configured styrylpyridine heterocyclic compound valued in organic synthesis and photochemical research for its conjugated aromatic framework and geometric stability.

Chemical Name

2-Methyl-6-[(E)-2-phenylethenyl]pyridine

SKU

S613579

Molecular Formula

C14H13N

Molecular Weight

195.26 g/mol

Stereochemistry

E (trans) configuration at the vinyl double bond

Core Scaffold

Pyridine ring substituted at positions 2 and 6 with methyl and (E)-styryl groups

Supplier

Aladdin Scientific

Chemical Structure and Physicochemical Properties

2-Methyl-6-[(E)-2-phenylethenyl]pyridine (SKU: S613579) belongs to the styrylpyridine family of heterocyclic compounds. Its molecular formula is C₁₄H₁₃N with a molecular weight of approximately 195.26 g/mol. The molecule features a pyridine ring bearing a methyl group at position 2 and a trans (E)-configured styryl substituent at position 6, creating an extended π-conjugated system across the pyridine and phenyl rings.

The E-configuration of the vinyl bridge confers geometric stability relative to the Z-isomer and is responsible for the characteristic photophysical behavior observed in styrylpyridine compounds, including UV–visible absorption in the near-UV region. The compound is expected to be a solid or low-melting solid at room temperature; exact melting point and solubility data should be confirmed from the Certificate of Analysis supplied with each lot.

Handling, Storage, and Safety

As with all fine chemical reagents, appropriate laboratory safety practices must be followed when working with 2-Methyl-6-[(E)-2-phenylethenyl]pyridine. Personnel should wear appropriate personal protective equipment (PPE) including nitrile gloves, safety glasses, and a laboratory coat. Operations producing dust or aerosols should be performed in a fume hood.

The compound should be stored in a tightly sealed container, protected from light, heat, and moisture to prevent photoisomerization of the E-configured double bond and to maintain chemical integrity over time. Storage at cool, dry conditions (typically 2–8 °C or per lot-specific CoA recommendations) is advised. Consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for complete hazard classification, first-aid measures, and disposal guidance before use.

Research Applications

Styrylpyridine derivatives, including 2-Methyl-6-[(E)-2-phenylethenyl]pyridine, are of interest across several research disciplines. Their extended conjugated frameworks make them useful building blocks or intermediates in:

• Organic and medicinal chemistry: The compound serves as a versatile scaffold for constructing more complex nitrogen-containing heterocycles via cross-coupling, cycloaddition, or condensation reactions.
• Photochemistry and photophysics: The E-configured styrylpyridine chromophore undergoes reversible E/Z photoisomerization under UV irradiation, a property explored in photoresponsive materials and molecular switches.
• Coordination chemistry: The pyridine nitrogen acts as a Lewis-basic coordination site, enabling the formation of metal complexes for catalysis or sensing applications.
• Fluorescence and optical materials research: Conjugated styrylpyridine frameworks are investigated as fluorescent probes or components of organic electronic devices.

Researchers should verify suitability for specific applications through their own experimental validation.

Quality, Purity, and Ordering Information

Aladdin Scientific supplies 2-Methyl-6-[(E)-2-phenylethenyl]pyridine under SKU S613579. Each lot is accompanied by a Certificate of Analysis (CoA) specifying purity, appearance, and analytical data including spectroscopic confirmation of the E-stereochemistry. Researchers and procurement teams are advised to request the CoA prior to use and to verify that the stated purity meets the requirements of the intended application.

For pricing, available pack sizes, current stock status, and volume discount inquiries, please contact Aladdin Scientific sales or visit the product page for SKU S613579 on the Aladdin Scientific website. Custom quantities or special purity grades may be available upon request.

Frequently asked questions

What is the stereochemistry of 2-Methyl-6-[(E)-2-phenylethenyl]pyridine and why does it matter?

The compound has an E (trans) configuration at the vinyl double bond connecting the pyridine and phenyl rings. This geometry determines the extent of π-conjugation and the compound's photophysical properties, including UV absorption wavelength and susceptibility to photoisomerization. Reaction outcomes in downstream synthesis may also differ between E and Z isomers, so confirming stereochemistry via the lot CoA is recommended.

How should I store 2-Methyl-6-[(E)-2-phenylethenyl]pyridine to prevent degradation?

Store the compound in a tightly sealed, light-resistant container under cool, dry conditions. Prolonged exposure to UV or visible light can drive E-to-Z photoisomerization, reducing the proportion of the desired isomer. Refer to the lot-specific CoA and SDS from Aladdin Scientific for precise temperature and storage recommendations.

What solvents are suitable for dissolving 2-Methyl-6-[(E)-2-phenylethenyl]pyridine?

Based on the compound's conjugated aromatic structure and relatively nonpolar character, common organic solvents such as dichloromethane, chloroform, ethyl acetate, acetonitrile, or DMSO are likely to provide good solubility. Solubility in water is expected to be very low. Actual solubility should be confirmed experimentally, and solvent selection should be guided by the intended application.

Is 2-Methyl-6-[(E)-2-phenylethenyl]pyridine suitable for coordination chemistry applications?

Yes, the pyridine nitrogen in this compound is a classical Lewis-basic coordination site capable of binding transition metals. The 2,6-disubstituted pyridine pattern, with a methyl group and a styryl arm, may influence the steric and electronic environment around the metal center, making it a potentially interesting ligand candidate. Coordination chemistry applications should be verified through experimental work.

References

1. Aladdin Scientific product page for 2-Methyl-6-[(E)-2-phenylethenyl]pyridine, SKU S613579.
2. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; Wiley-Interscience: New York, 1992. (General reference for styryl and heterocyclic chemistry.)
3. Saltiel, J.; Charlton, J. L. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic Press, 1980; Vol. 3. (Reference for E/Z photoisomerization of stilbene-type compounds.)

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