2-Benzylidene-1-tetralone: Properties, Uses & FAQs
2-Benzylidene-1-tetralone: Properties, Uses & FAQs
2-Benzylidene-1-tetralone is an organic compound featuring a benzylidene substituent at the 2-position of the 3,4-dihydronaphthalenone (tetralone) scaffold, making it a valuable synthetic intermediate and research reagent in medicinal and synthetic organic chemistry.
- Chemical Name
- 2-Benzylidene-1-tetralone (2-benzylidene-3,4-dihydronaphthalen-1(2H)-one)
- Molecular Formula
- C17H14O
- Molecular Weight
- 234.29 g/mol
- Core Scaffold
- Tetralone (3,4-dihydronaphthalen-1(2H)-one) with an exocyclic benzylidene group at C-2
- Functional Class
- Enone / chalcone analogue; synthetic intermediate
- Aladdin SKU
- B709730
What Is 2-Benzylidene-1-tetralone?
2-Benzylidene-1-tetralone is an α,β-unsaturated ketone (enone) in which a benzylidene (PhCH=) group is conjugated with the carbonyl of a tetralone ring system. The compound belongs to the broader class of chalcone analogues and constrained enones, where the cyclohexanone ring of tetralone restricts the conformational flexibility of the enone moiety. This rigidity can confer selectivity advantages in downstream reactions and biological interactions.
The molecular formula is C17H14O, with a molecular weight of approximately 234.29 g/mol. The compound is typically a pale yellow to yellow crystalline solid at room temperature.
Synthesis and Chemical Reactivity
2-Benzylidene-1-tetralone is most commonly prepared via an aldol condensation (Knoevenagel-type reaction) between 1-tetralone and benzaldehyde under basic or acidic catalysis, with loss of water to yield the α,β-unsaturated product. This reaction is straightforward and typically affords the (E)-isomer preferentially due to steric factors.
As a Michael acceptor, the compound participates in 1,4-conjugate addition reactions with nucleophiles including amines, thiols, and carbon nucleophiles, providing access to a range of 2-substituted tetralone derivatives. It can also undergo Diels-Alder cycloadditions when used as a dienophile, and it serves as a versatile building block for the synthesis of polycyclic natural product analogues and pharmaceutical scaffolds.
Storage, Handling, and Safety
Store 2-Benzylidene-1-tetralone in a tightly sealed container in a cool, dry, and well-ventilated location away from direct light and heat sources. As with most organic enones, the compound should be handled with appropriate personal protective equipment (PPE) including gloves, safety glasses, and a lab coat. Avoid inhalation of dust or vapors.
Consult the current Safety Data Sheet (SDS) before use. Specific hazard classifications, GHS pictograms, and first-aid measures are detailed in the SDS provided by Aladdin Scientific for SKU B709730. Waste disposal must comply with local and institutional regulations for organic chemical waste.
Ordering and Specifications
2-Benzylidene-1-tetralone is available from Aladdin Scientific under SKU B709730. Customers should confirm available pack sizes, purity grade, and current stock status through the Aladdin product page or by contacting our technical support team.
For bulk or custom quantities, please submit an inquiry via the Aladdin website or contact your regional sales representative. Certificates of Analysis (CoA) are available upon request and can be downloaded from the product page using the lot number printed on the label.
Research Applications
Because of its constrained enone architecture, 2-Benzylidene-1-tetralone finds application as an intermediate in the synthesis of biologically active tetralone-based compounds, including potential anti-inflammatory, anticancer, and antimicrobial agents investigated in the literature. The scaffold mimics chalcones while imposing conformational restriction, which researchers exploit to study structure-activity relationships (SAR).
The compound is also used in methodology studies exploring asymmetric conjugate addition, organocatalysis, and transition-metal-catalyzed transformations. Its well-defined geometry and commercially available status make it a practical reference substrate for synthetic method development.
Frequently asked questions
What is the CAS number of 2-Benzylidene-1-tetralone?
The CAS number for 2-Benzylidene-1-tetralone should be confirmed directly from the Aladdin product page or the Certificate of Analysis for SKU B709730, as this information was not specified in the current source material. Please contact Aladdin Scientific technical support for verification.
What purity grade is 2-Benzylidene-1-tetralone available in from Aladdin Scientific?
Purity specifications for SKU B709730 are listed on the Aladdin Scientific product page and in the accompanying Certificate of Analysis. Customers requiring a specific purity grade for sensitive applications should download the CoA using their lot number or contact our support team before purchase.
How should 2-Benzylidene-1-tetralone be stored to maintain stability?
Store the compound in a tightly closed container in a cool, dry, dark place away from oxidizing agents and strong acids or bases. Refrigerated storage (2–8 °C) may be recommended for long-term stability; refer to the SDS and CoA for lot-specific guidance.
Is 2-Benzylidene-1-tetralone soluble in common organic solvents?
As a non-polar to moderately polar organic solid, 2-Benzylidene-1-tetralone is expected to dissolve readily in common organic solvents such as dichloromethane, chloroform, ethyl acetate, and DMSO, with limited solubility in water. Exact solubility data should be verified experimentally or sourced from the SDS.
Can 2-Benzylidene-1-tetralone be used as a Michael acceptor in organic synthesis?
Yes, the conjugated enone system of 2-Benzylidene-1-tetralone makes it an effective Michael acceptor, capable of reacting with a variety of soft nucleophiles including amines, thiols, and stabilized carbanions at the beta-carbon of the enone. This property makes it a useful building block for diversifying the tetralone scaffold.
References
- Aladdin Scientific product page for 2-Benzylidene-1-tetralone, SKU B709730. Aladdin Scientific Corp.
- March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. 4th ed. Wiley-Interscience, 1992. (General reference for aldol condensation and Michael addition reactions.)
- Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry. 2nd ed. Oxford University Press, 2012. (Textbook reference for enone reactivity and conjugate addition.)
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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