3-(5-Methylisoxazol-3-yl)-3-oxopropanenitrile: Properties & Lab Guide
3-(5-Methylisoxazol-3-yl)-3-oxopropanenitrile: Properties & Lab Guide
3-(5-Methylisoxazol-3-yl)-3-oxopropanenitrile is a bifunctional heterocyclic building block combining a reactive beta-ketonitrile moiety with a 5-methylisoxazole ring, making it a versatile intermediate for medicinal chemistry and organic synthesis applications.
- Chemical Name
- 3-(5-Methylisoxazol-3-yl)-3-oxopropanenitrile
- Core Functional Groups
- Beta-ketonitrile and methylisoxazole ring
- Compound Class
- Heterocyclic beta-ketonitrile
- Primary Application
- Organic synthesis intermediate and medicinal chemistry building block
- SKU
- O692070
- Supplier
- Aladdin Scientific
Chemical Identity and Structure
3-(5-Methylisoxazol-3-yl)-3-oxopropanenitrile is a heterocyclic organic compound featuring two distinct reactive sites: a nitrile (–CN) group and a ketone carbonyl (C=O) connected through a methylene bridge, together constituting a beta-ketonitrile motif. This motif is appended directly to the C-3 position of a 5-methylisoxazole ring.
The isoxazole ring is a five-membered aromatic heterocycle containing one oxygen and one nitrogen atom. The methyl substituent at the C-5 position modulates the electron density of the ring and influences the reactivity of the adjacent carbonyl. The combination of a nitrogen-containing heterocycle and the highly activated methylene group between the nitrile and ketone renders this molecule particularly suitable as a synthetic building block.
The beta-ketonitrile segment is well known for its high acidity at the active methylene position, facilitating condensation reactions, cyclizations, and chelation with metal ions—properties that are exploited in diverse synthetic strategies.
Handling, Storage, and Safety Guidelines
As with all beta-ketonitrile compounds, appropriate personal protective equipment (PPE) should be worn when handling 3-(5-Methylisoxazol-3-yl)-3-oxopropanenitrile. This includes nitrile gloves, safety goggles, and a laboratory coat. Operations should be conducted in a well-ventilated fume hood, particularly when weighing or dissolving the compound.
The compound should be stored in a tightly sealed container, away from moisture, heat, and direct sunlight. Storage under cool, dry conditions (typically 2–8 °C or room temperature as specified on the product label) is recommended to maintain stability and prevent degradation of the sensitive nitrile and carbonyl functionalities.
Consult the Safety Data Sheet (SDS) provided by Aladdin Scientific before use. In the event of skin or eye contact, rinse immediately with copious amounts of water and seek medical advice. Disposal should comply with applicable local regulations for chemical waste.
Research Applications and Synthetic Utility
3-(5-Methylisoxazol-3-yl)-3-oxopropanenitrile serves as a valuable building block in heterocyclic chemistry. The highly activated methylene group between the nitrile and ketone functionalities participates readily in Knoevenagel condensations, Michael additions, and cyclocondensation reactions with a variety of electrophiles and dinucleophiles, enabling access to complex polycyclic and fused heterocyclic frameworks.
In medicinal chemistry, isoxazole-containing scaffolds are frequently encountered in biologically active compounds. The 5-methylisoxazol-3-yl ketone unit can serve as a pharmacophore or as a handle for further derivatization to generate compound libraries for biological screening.
The beta-ketonitrile group also confers metal-chelating capability, which may be exploited in catalyst design and coordination chemistry studies. Researchers working on agrochemical, pharmaceutical, or materials science applications may find this compound useful as a precursor for more complex targets.
Ordering and Quality Assurance
3-(5-Methylisoxazol-3-yl)-3-oxopropanenitrile is available from Aladdin Scientific under SKU O692070. Aladdin Scientific supplies research-grade reagents with associated lot-specific analytical data, including purity information determined by standard analytical techniques such as HPLC or NMR, where applicable.
Researchers and procurement officers are encouraged to request a Certificate of Analysis (CoA) for each lot to confirm that the material meets specification before use in critical experiments. For bulk or custom quantity inquiries, please contact Aladdin Scientific customer service directly.
All orders are subject to Aladdin Scientific's standard terms and conditions regarding payment, shipping, returns, and applicable export regulations. Please consult the Aladdin Scientific website or your regional representative for current pricing and availability.
Frequently asked questions
What is 3-(5-Methylisoxazol-3-yl)-3-oxopropanenitrile used for in research?
This compound is primarily used as a heterocyclic building block in organic synthesis, particularly in the preparation of complex fused or polycyclic heterocyclic frameworks via condensation and cyclocondensation reactions. Its isoxazole-containing scaffold is also of interest in medicinal chemistry for the development of biologically active molecules.
How should 3-(5-Methylisoxazol-3-yl)-3-oxopropanenitrile be stored to maintain its stability?
The compound should be stored in a tightly sealed container under cool, dry conditions away from moisture, heat, and direct light. Consult the product label and the Aladdin Scientific Safety Data Sheet for lot-specific storage recommendations.
What reactive sites does this compound offer for synthetic transformations?
The compound contains two principal reactive sites: the nitrile group and the ketone carbonyl, flanking a highly acidic active methylene group that readily undergoes Knoevenagel condensations, Michael additions, and cyclocondensations. The isoxazole ring nitrogen can also participate in coordination or further functionalization reactions.
Where can I obtain a Certificate of Analysis for SKU O692070?
A Certificate of Analysis (CoA) for each lot of SKU O692070 can be requested directly from Aladdin Scientific customer service or downloaded from the Aladdin Scientific product page where available. The CoA includes purity and analytical data specific to your lot.
References
- Aladdin Scientific product listing: 3-(5-Methylisoxazol-3-yl)-3-oxopropanenitrile, SKU O692070.
- General reference: Joule, J. A.; Mills, K. Heterocyclic Chemistry, 5th ed.; Wiley-Blackwell, 2010. (Textbook-level source for isoxazole chemistry.)
- General reference: Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press, 2012. (Textbook-level source for beta-ketonitrile reactivity.)
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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