2-Butyl-2-octenal: Properties, Uses & Handling FAQ

2-Butyl-2-octenal is a branched-chain α,β-unsaturated aldehyde valued in organic synthesis and flavour-fragrance research as a versatile electrophilic building block bearing both a reactive enal functionality and extended alkyl substituents.

Chemical Name

2-Butyl-2-octenal

Compound Class

α,β-Unsaturated aldehyde (enal)

Aladdin SKU

B485358

Molecular Formula

C12H22O

Molecular Weight

182.30 g/mol

Key Functional Group

α,β-Unsaturated aldehyde (conjugated C=C–C=O)

Typical Applications

Organic synthesis intermediate; flavour & fragrance research

What Is 2-Butyl-2-octenal and How Is It Prepared?

2-Butyl-2-octenal (molecular formula C₁₂H₂₂O, MW ≈ 182.30 g/mol) is a twelve-carbon α,β-unsaturated aldehyde in which the double bond is conjugated with the carbonyl group at the 2-position, and a butyl chain is attached at the same carbon. This arrangement creates a fully substituted α-carbon and imparts significant steric and electronic character to the molecule.

The compound is most commonly accessed via aldol condensation chemistry. A base- or acid-catalysed self-condensation or crossed aldol reaction between appropriate aliphatic aldehydes (e.g., hexanal and valeraldehyde or related homologues) followed by dehydration gives the α,β-unsaturated aldehyde skeleton. The extended branched structure makes it resistant to further self-condensation under mild conditions, which simplifies isolation.

At Aladdin Scientific, 2-Butyl-2-octenal is supplied as a neat liquid reagent under SKU B485358, ready for direct use in synthetic workflows.

Chemical Properties and Reactivity

As an α,β-unsaturated aldehyde, 2-Butyl-2-octenal participates in both 1,2-addition (at the carbonyl carbon) and 1,4-conjugate addition (Michael addition) reactions. Soft nucleophiles such as organocuprates, stabilised carbanions, and thiols preferentially attack the β-carbon (C-3), while hard nucleophiles such as organolithium reagents tend to give 1,2-addition products at the carbonyl.

The aldehyde group can also be selectively reduced to the allylic alcohol using reagents such as DIBAL-H or NaBH₄ under controlled conditions, or oxidised to the corresponding carboxylic acid. The conjugated system makes the compound a reactive Michael acceptor, which is relevant both in synthetic applications and in its biological reactivity profile.

The lipophilic C₁₂ skeleton confers low water solubility and miscibility with common organic solvents (dichloromethane, ethyl acetate, hexane, THF). The compound should be treated as a reactive electrophile and handled accordingly.

Storage, Stability, and Safe Handling

Storage: Store 2-Butyl-2-octenal in a tightly sealed container away from light, heat, and oxidising agents. A cool, dry environment (2–8 °C or as indicated on the product label) under an inert atmosphere (nitrogen or argon) is recommended to minimise oxidation and polymerisation of the conjugated enal system.

Stability: α,β-Unsaturated aldehydes can undergo slow autoxidation on prolonged exposure to air and may oligomerise under acidic or basic conditions. Freshly opened reagent should be used promptly; residual material should be stored under inert gas with a desiccant.

Safe Handling: As an unsaturated aldehyde, 2-Butyl-2-octenal is a potential skin, eye, and respiratory irritant and a reactive Michael acceptor capable of forming adducts with biological nucleophiles (e.g., cysteine residues in proteins). Use appropriate personal protective equipment (nitrile gloves, safety glasses, lab coat) and work in a well-ventilated fume hood. Consult the Safety Data Sheet (SDS) provided by Aladdin Scientific before use for jurisdiction-specific hazard classifications and first-aid procedures.

Applications in Research and Industry

Organic Synthesis: 2-Butyl-2-octenal serves as a versatile C₁₂ building block for the construction of complex molecules. Its enal functionality enables Wittig, Horner–Wadsworth–Emmons, and Knoevenagel reactions at the aldehyde end, while the activated double bond allows conjugate additions to introduce nucleophilic fragments at the β-position. It can be incorporated into natural product synthesis, pharmaceutical intermediates, and specialty chemical pathways.

Flavour and Fragrance Research: Branched long-chain enals are well-recognised in flavour chemistry for their organoleptic contributions — typically fatty, green, or citrus-like descriptors depending on chain length and branching. 2-Butyl-2-octenal may be evaluated as a reference standard, an aroma descriptor, or a synthetic precursor to fragrance molecules in academic and industrial flavour research programmes.

Biochemical and Toxicological Studies: α,β-Unsaturated aldehydes are important substrates in studies of electrophile–nucleophile interactions, protein adduct formation, and cellular stress responses. 2-Butyl-2-octenal may be used as a model enal compound in such mechanistic investigations.

Ordering and Specification Information

2-Butyl-2-octenal is available from Aladdin Scientific under SKU B485358. To place an order, visit the Aladdin Scientific website, search by product name or SKU, and add the desired quantity to your cart. Bulk quantities and custom packaging may be available upon request — contact our sales team for a quotation.

When evaluating the reagent for your application, please request the current Certificate of Analysis (CoA) for the specific lot you are purchasing. The CoA will detail purity (typically assessed by GC), appearance, and any additional quality parameters relevant to your workflow.

For technical questions regarding this product, our scientific support team is available via the contact channels listed on the Aladdin Scientific website. Returns and refunds are handled in accordance with our standard reagent return policy; please review the terms on our website or contact customer service prior to initiating a return.

Frequently asked questions

What is the molecular formula and molecular weight of 2-Butyl-2-octenal?

2-Butyl-2-octenal has the molecular formula C₁₂H₂₂O and a molecular weight of approximately 182.30 g/mol. It is a twelve-carbon branched α,β-unsaturated aldehyde.

How should 2-Butyl-2-octenal be stored to maintain its stability?

Store 2-Butyl-2-octenal in a tightly sealed, light-resistant container under an inert atmosphere (nitrogen or argon) at cool temperatures (2–8 °C or as specified on the product label). These conditions minimise oxidation and polymerisation of the reactive conjugated enal system. Always consult the product label and SDS for the most current storage recommendations.

What types of chemical reactions can 2-Butyl-2-octenal undergo?

As an α,β-unsaturated aldehyde, 2-Butyl-2-octenal undergoes 1,2-addition at the carbonyl (favoured by hard nucleophiles such as organolithiums) and 1,4-conjugate Michael addition at the β-carbon (favoured by soft nucleophiles such as organocuprates and thiols). The aldehyde can also be selectively reduced to the allylic alcohol or oxidised to the carboxylic acid, and the aldehyde terminus is amenable to Wittig and related olefination reactions.

What safety precautions should I take when handling 2-Butyl-2-octenal?

Wear nitrile gloves, safety glasses, and a lab coat, and handle the compound in a well-ventilated fume hood. As an α,β-unsaturated aldehyde, it is a potential skin, eye, and respiratory irritant and a reactive electrophile. Review the Safety Data Sheet (SDS) available from Aladdin Scientific before first use for complete hazard information.

What is the Aladdin Scientific SKU for 2-Butyl-2-octenal and how can I order it?

2-Butyl-2-octenal is available under SKU B485358 at Aladdin Scientific. You can order online through the Aladdin Scientific website by searching for the product name or SKU number and adding your required quantity to the cart. For bulk orders or technical enquiries, contact the Aladdin Scientific sales or support team directly.

What purity and quality documentation is available for 2-Butyl-2-octenal (B485358)?

A lot-specific Certificate of Analysis (CoA) is available for each batch of 2-Butyl-2-octenal (SKU B485358). The CoA typically includes purity data (assessed by GC), appearance, and other quality parameters. Request the CoA for your specific lot through the Aladdin Scientific website or by contacting customer service.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; Wiley-Interscience: New York, 1992. (General reference for aldol condensation and α,β-unsaturated carbonyl reactivity.)
2. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (Textbook-level reference for conjugate addition and enal chemistry.)
3. Aladdin Scientific. Product Page: 2-Butyl-2-octenal, SKU B485358. Aladdin Scientific website (accessed 2024).

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