5-Methyl-2-phenyl-2-hexenal: Properties, Uses & FAQs

5-Methyl-2-phenyl-2-hexenal is an alpha,beta-unsaturated aldehyde (enal) featuring a phenyl substituent at the 2-position and an isoamyl branch at the 5-position, making it a versatile building block in organic synthesis and fragrance research.

Chemical Name

5-Methyl-2-phenyl-2-hexenal

SKU / Catalog Number

M107640

Functional Class

Alpha,beta-unsaturated aldehyde (enal)

Key Structural Features

Phenyl group at C-2, isoamyl branch at C-5, conjugated C=C–C=O system

Primary Research Applications

Organic synthesis intermediate, fragrance chemistry research, Michael acceptor in reaction methodology

Supplier

Aladdin Scientific

Chemical Identity and Structure

5-Methyl-2-phenyl-2-hexenal belongs to the class of alpha,beta-unsaturated aldehydes (enals). Its backbone is a six-carbon chain bearing a phenyl substituent at the 2-position and a methyl branch at the 5-position, which together create an isoamyl-type terminus. The conjugated system formed by the carbon–carbon double bond and the carbonyl group is central to the compound's reactivity, enabling participation in 1,2- and 1,4-addition reactions (Michael additions) with a wide range of nucleophiles.

The structural combination of an aromatic ring and an aliphatic branched chain confers both lipophilic character and a characteristic floral-green odor profile, which accounts for interest in this compound within the flavor and fragrance industry as well as in academic synthetic chemistry.

Physicochemical Properties and Storage

As an alpha,beta-unsaturated aldehyde, 5-Methyl-2-phenyl-2-hexenal is an electrophilically activated compound. Key physicochemical considerations include its sensitivity to air oxidation and light, which can lead to discoloration or formation of peroxide impurities over time. Researchers should verify the current specification sheet available from Aladdin Scientific (SKU M107640) for confirmed values of molecular weight, purity, boiling point, refractive index, and density, as these parameters may vary by lot.

Recommended storage conditions for alpha,beta-unsaturated aldehydes of this type generally include storage under inert atmosphere (nitrogen or argon), in a cool, dark location, and with use of amber glassware where feasible. Always consult the product Safety Data Sheet (SDS) before handling.

Research Applications

Organic Synthesis: The activated double bond of 5-Methyl-2-phenyl-2-hexenal makes it a useful Michael acceptor in asymmetric organocatalysis and metal-catalyzed conjugate addition methodologies. Enals of this structural type have been employed in Diels-Alder reactions (as dienophiles), Morita-Baylis-Hillman reactions, and as precursors to chiral building blocks via organocatalytic cascade reactions.

Fragrance Research: Alpha,beta-unsaturated aldehydes with aryl substitution are well-established fragrance materials. 5-Methyl-2-phenyl-2-hexenal may serve as a reference standard, synthetic target, or intermediate in studies aimed at structure-odor relationship research.

Reaction Methodology Studies: Its defined conjugated electrophilic framework makes it suitable as a model substrate for benchmarking new catalytic systems, including NHC (N-heterocyclic carbene) catalysis and secondary amine organocatalysis involving enamine or iminium ion intermediates.

Safe Handling and Regulatory Considerations

Alpha,beta-unsaturated aldehydes are generally considered reactive electrophiles and potential skin and respiratory sensitizers. Researchers should treat 5-Methyl-2-phenyl-2-hexenal with appropriate caution: use in a well-ventilated fume hood, wear nitrile gloves, safety glasses, and a lab coat. Avoid inhalation of vapors.

Before use, download and review the current Safety Data Sheet (SDS) for M107640 from the Aladdin Scientific website. Disposal must comply with applicable local, national, and institutional regulations for chemical waste. Note that regulatory classifications (GHS hazard categories, transport classification) should be verified from the SDS, as these are lot- and jurisdiction-specific.

Ordering and Technical Support

5-Methyl-2-phenyl-2-hexenal is available from Aladdin Scientific under catalog number M107640. To place an order, visit the Aladdin Scientific website, search by SKU or product name, and select the appropriate pack size and quantity. Bulk or custom quantities may be available upon request — contact Aladdin Scientific's sales team for a quotation.

For technical questions regarding purity certificates (CoA), Safety Data Sheets (SDS), or specific analytical data, contact Aladdin Scientific technical support. Lot-specific documentation can typically be requested via the product page or customer service portal.

Frequently asked questions

What is 5-Methyl-2-phenyl-2-hexenal used for in research?

5-Methyl-2-phenyl-2-hexenal is primarily used as an organic synthesis intermediate and as a Michael acceptor in organocatalytic and metal-catalyzed reactions. It also serves as a reference or synthetic target in fragrance structure-odor relationship studies, and as a model substrate for evaluating new catalytic methodologies such as NHC catalysis and secondary amine organocatalysis.

How should 5-Methyl-2-phenyl-2-hexenal be stored to maintain stability?

This compound should be stored under an inert atmosphere (nitrogen or argon) in a cool, dark location to minimize oxidation and photodegradation. Use of amber glass containers is advisable. Always refer to the current Aladdin Scientific product SDS and Certificate of Analysis for lot-specific storage recommendations.

Is 5-Methyl-2-phenyl-2-hexenal hazardous, and what safety precautions are required?

As an alpha,beta-unsaturated aldehyde, this compound may act as a reactive electrophile and potential sensitizer. Handle in a well-ventilated fume hood, wearing nitrile gloves, safety glasses, and a lab coat. Avoid inhalation of vapors and skin contact. Download the current SDS for M107640 from Aladdin Scientific before first use.

What catalog number should I use to order 5-Methyl-2-phenyl-2-hexenal from Aladdin Scientific?

The catalog number for 5-Methyl-2-phenyl-2-hexenal at Aladdin Scientific is M107640. You can search this SKU directly on the Aladdin Scientific website to view available pack sizes, current pricing, and to request a Certificate of Analysis or SDS.

Can 5-Methyl-2-phenyl-2-hexenal be used as a Michael acceptor in organocatalytic reactions?

Yes. The conjugated C=C–C=O system in 5-Methyl-2-phenyl-2-hexenal activates the beta-carbon toward nucleophilic 1,4-addition. This property makes it a suitable substrate for organocatalytic Michael additions, including those mediated by secondary amines (via iminium ion activation) or NHC catalysts. Researchers should optimize reaction conditions for their specific nucleophile and catalyst system.

References

1. Aladdin Scientific product page: 5-Methyl-2-phenyl-2-hexenal, SKU M107640. Aladdin Scientific (accessed 2024).
2. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. General reference for alpha,beta-unsaturated carbonyl reactivity.
3. MacMillan, D. W. C. The advent and development of organocatalysis. Nature 2008, 455, 304–308. Background on organocatalytic activation modes relevant to enal substrates. doi:10.1038/nature07367

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