What Is 3-Phenylcyclobutanone?

3-Phenylcyclobutanone is an organic compound consisting of a cyclobutanone scaffold — a four-membered carbocyclic ring containing a ketone carbonyl — substituted with a phenyl group at the 3-position. The combination of a reactive ketone and significant ring strain (arising from the compressed C–C–C bond angles of the four-membered ring) makes this molecule highly reactive toward a variety of synthetic transformations.

The compound belongs to the broader class of strained-ring ketones. Cyclobutanone derivatives, including 3-Phenylcyclobutanone, have attracted considerable attention as synthetic intermediates due to their ability to undergo strain-releasing ring-expansion and ring-opening reactions, as well as conventional carbonyl chemistry including nucleophilic addition, enolization, and condensation reactions.

Aladdin Scientific supplies 3-Phenylcyclobutanone under SKU P589371B, offering researchers reliable access to this specialized building block.

Physicochemical Properties and Structure

The molecular structure of 3-Phenylcyclobutanone features an sp2 carbonyl carbon within a four-membered ring, which imposes approximately 90° internal bond angles — significantly compressed relative to the ideal tetrahedral angle of 109.5°. This angle strain contributes to elevated ring strain energy and enhanced electrophilicity of the carbonyl group compared to unstrained cyclic or acyclic ketones.

The phenyl group at the 3-position (the carbon directly opposite the carbonyl) exerts both steric and electronic effects on the ring system. Through-space and hyperconjugative interactions between the aromatic ring and the cyclobutanone system can influence conformational preferences and reaction selectivity.

Note: Specific numerical values for molecular weight, melting point, boiling point, and purity are not reproduced here without verified source data. Please refer to the Aladdin Scientific product specification sheet for P589371B for confirmed physicochemical data.

Synthetic Applications and Research Uses

3-Phenylcyclobutanone serves as a versatile synthetic intermediate, primarily valued for its dual reactivity: conventional ketone chemistry at the carbonyl center and strain-driven transformations of the cyclobutane ring.

• Ring-expansion reactions: Cyclobutanones are classical substrates for Baeyer–Villiger oxidation, which inserts an oxygen atom adjacent to the carbonyl to yield the corresponding lactone (in this case, a five-membered δ-lactone). This provides a route to medium-ring or functionalized lactone frameworks.
• Nucleophilic addition: Grignard reagents, organolithiums, and hydride reducing agents can add to the carbonyl of 3-Phenylcyclobutanone to afford cyclobutanol derivatives, which are themselves useful building blocks.
• Ring-opening chemistry: Under certain conditions, the strained ring can participate in retro-[2+2] or metal-catalyzed C–C bond activation processes, enabling ring-opening to access functionalized acyclic or larger-ring products.
• Enolate chemistry: Deprotonation alpha to the carbonyl generates cyclobutanone enolates capable of alkylation, aldol, and Michael reactions.

These attributes make 3-Phenylcyclobutanone useful in the synthesis of pharmaceutically relevant scaffolds, natural product analogs, and strained-ring building blocks for medicinal chemistry programs.

Handling, Storage, and Safety Considerations

As with most strained-ring ketone intermediates, appropriate precautions should be observed when handling 3-Phenylcyclobutanone in the laboratory:

• Storage: Store in a cool, dry, well-ventilated location away from heat sources, oxidizing agents, and strong bases or acids. Consult the Aladdin Scientific Safety Data Sheet (SDS) for P589371B for specific storage temperature recommendations.
• Personal Protective Equipment (PPE): Use appropriate PPE including chemical-resistant gloves, laboratory coat, and eye protection. Work in a fume hood when handling in bulk or when volatility is a concern.
• Incompatibilities: Avoid contact with strong oxidizing agents, strong reducing agents, and reactive metals. The ketone functionality may react with nucleophilic reagents under ambient conditions.
• Disposal: Dispose of in accordance with local, regional, and national regulations for organic chemical waste.

For full hazard classification, GHS pictograms, first-aid measures, and regulatory information, always refer to the current SDS provided by Aladdin Scientific for SKU P589371B.

Ordering and Product Information

3-Phenylcyclobutanone is available from Aladdin Scientific under the following details:

• Product Name: 3-Phenylcyclobutanone
• SKU: P589371B
• Supplier: Aladdin Scientific

To place an order or to request a quotation, visit the Aladdin Scientific website and search by SKU P589371B, or contact your regional Aladdin Scientific sales representative. Bulk quantities and custom packaging may be available upon request.

For technical questions regarding purity specifications, certificate of analysis (CoA), or application suitability, please contact Aladdin Scientific technical support. Ensure you request the current SDS and CoA at the time of ordering to confirm that the material meets your experimental requirements.