4-Tridecanone: Properties, Uses & Lab Guide

4-Tridecanone is a long-chain aliphatic methyl ketone with the molecular formula C13H26O, valued in organic synthesis and chemical research for its characteristic carbonyl reactivity and hydrophobic alkyl chain.

Molecular Formula

C13H26O

Molecular Weight

198.35 g/mol

Functional Group

Ketone (C=O) at position 4

Physical State

Liquid at room temperature (typical for C13 aliphatic ketones)

Aladdin SKU

T335186

Solubility

Miscible with common organic solvents (e.g., ethanol, diethyl ether, chloroform); poorly soluble in water

Chemical Identity and Structure

4-Tridecanone (systematic IUPAC name: tridecan-4-one) is a straight-chain aliphatic ketone in which the carbonyl group is located at the fourth carbon of a thirteen-carbon backbone. Its molecular formula is C₁₃H₂₆O with a molecular weight of approximately 198.35 g/mol. The compound belongs to the broader class of methyl-substituted ketones and shares structural features with other medium- to long-chain aliphatic ketones such as 2-tridecanone and undecan-2-one.

The internal placement of the carbonyl group at C-4 distinguishes 4-tridecanone from the more common terminal (methyl) ketone isomers, conferring subtly different reactivity profiles in nucleophilic addition reactions and enolization chemistry. The extended nonyl chain on one face of the carbonyl imparts significant hydrophobicity, influencing partitioning behavior and solubility.

Physical and Chemical Properties

As a C13 aliphatic ketone, 4-tridecanone is expected to be a colorless to pale yellow liquid at ambient temperature, with a faint waxy or ketonic odor characteristic of long-chain ketones. Key physicochemical parameters—including exact boiling point, melting point, density, refractive index, and flash point—should be confirmed from the certificate of analysis (CoA) supplied with each lot, as these values can vary with purity.

The compound exhibits low water solubility consistent with its high log P (estimated >4 for C13 ketones), making it readily partitioned into organic phases during liquid–liquid extraction. It is compatible with standard organic solvents including dichloromethane, tetrahydrofuran, ethyl acetate, and hexane, facilitating its use in typical synthetic workup procedures.

The ketone carbonyl is reactive toward common nucleophiles (Grignard reagents, organolithium compounds, hydride reducing agents such as NaBH₄ and LiAlH₄), and can participate in aldol-type condensations under basic or acidic conditions. Oxidative stability is generally good under normal laboratory storage conditions.

Research and Synthesis Applications

Long-chain aliphatic ketones such as 4-tridecanone serve multiple roles in chemical research. In organic synthesis, the compound functions as a building block for the preparation of secondary alcohols (via reduction), tertiary alcohols (via organometallic addition), alkenes (via Wittig or related olefination reactions), and amines (via reductive amination). The C4-ketone regiochemistry also provides a handle for selective enolate formation and subsequent alkylation.

In chemical ecology and flavor/fragrance research, medium- and long-chain methyl ketones are known semiochemicals and aroma compounds. Structural analogs of 4-tridecanone have been studied in the context of insect pheromone chemistry and plant volatile profiles, making this compound a useful reference standard or synthetic intermediate in such investigations.

Additionally, aliphatic ketones in this chain-length range are employed as model substrates for enzyme activity assays (e.g., cytochrome P450 hydroxylation studies, ketoreductase screening), providing a hydrophobic substrate with defined chain length and carbonyl position.

Safe Handling, Storage, and Regulatory Considerations

As with all organic carbonyl compounds, 4-tridecanone should be handled with standard laboratory precautions. Personal protective equipment (PPE) including chemical-resistant gloves, safety goggles, and a lab coat is recommended. Work should be performed in a well-ventilated area or fume hood to avoid inhalation of vapors.

Store 4-tridecanone in a tightly sealed container away from heat, open flames, and strong oxidizing agents, in a cool, dry, well-ventilated area consistent with flammable liquid storage guidelines. Consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for lot-specific hazard classification, GHS pictograms, first-aid measures, and disposal instructions prior to use.

Researchers should verify applicable local and institutional regulations regarding the transport, storage, and waste disposal of aliphatic ketones before ordering. No specific controlled-substance restrictions are anticipated for this compound class, but regulatory status should be confirmed independently.

Frequently asked questions

What is the CAS number for 4-Tridecanone?

The CAS registry number for 4-Tridecanone (tridecan-4-one) should be confirmed from the product's certificate of analysis or SDS. Aladdin Scientific's SKU T335186 corresponds to this compound; please contact Aladdin support or check the product page for the verified CAS number.

What solvents are compatible with 4-Tridecanone for solution preparation?

4-Tridecanone is miscible with common organic solvents including ethanol, dichloromethane, diethyl ether, ethyl acetate, tetrahydrofuran, and hexane. It has poor water solubility due to its long hydrophobic alkyl chain, so aqueous solutions should be prepared with co-solvents or surfactant-based systems if required.

How should 4-Tridecanone be stored to maintain stability?

Store 4-Tridecanone in a tightly closed container under cool, dry conditions away from direct light, heat sources, and strong oxidizing agents, following standard flammable organic liquid storage protocols. Always refer to the SDS provided with your Aladdin Scientific order for authoritative, lot-specific storage recommendations.

What are the typical synthetic uses of 4-Tridecanone in the laboratory?

4-Tridecanone serves as a versatile building block in organic synthesis, including nucleophilic additions with Grignard or organolithium reagents to yield tertiary alcohols, reduction to secondary alcohols, Wittig olefination to produce internal alkenes, and reductive amination to access amine derivatives. It is also used as a model hydrophobic substrate in enzyme assay development.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; Wiley-Interscience: New York, 1992. (General reference for ketone reactivity and synthetic transformations.)
2. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (Textbook-level reference for aliphatic ketone chemistry.)
3. Aladdin Scientific. Product page: 4-Tridecanone, SKU T335186. (Santa Cruz cross-reference: sc-267754.)

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