2-Amino-1-cyclopentene-1-carbonitrile: Properties & Uses
2-Amino-1-cyclopentene-1-carbonitrile: Properties & Uses
2-Amino-1-cyclopentene-1-carbonitrile is a cyclic enaminonitrile compound widely employed as a versatile synthetic building block in the preparation of nitrogen-containing heterocyclic compounds and pharmaceutically relevant scaffolds.
- Chemical Name
- 2-Amino-1-cyclopentene-1-carbonitrile
- SKU / Catalog Number
- A183484
- Molecular Formula
- C6H8N2
- Molecular Weight
- 108.14 g/mol
- Functional Class
- Cyclic enaminonitrile; synthetic building block
- Primary Application
- Heterocyclic synthesis, medicinal chemistry intermediate
Chemical Identity and Structure
2-Amino-1-cyclopentene-1-carbonitrile (CAS number to be confirmed; see review flag) belongs to the enaminonitrile family of compounds. Its core structure consists of a five-membered carbocyclic ring bearing an exocyclic amino group (–NH2) and a nitrile group (–CN) on adjacent sp2-hybridized carbons of the ring, creating a conjugated push–pull electronic system. This arrangement gives the molecule pronounced nucleophilic character at the amino nitrogen and electrophilic character at the nitrile carbon, making it highly reactive toward a broad range of electrophiles and nucleophiles. The molecular formula is C6H8N2 with a molecular weight of approximately 108.14 g/mol.
Synthesis and Research Applications
2-Amino-1-cyclopentene-1-carbonitrile is most commonly prepared by the reaction of cyclopentanone with malononitrile in the presence of a base, via a Knoevenagel-type condensation followed by tautomerization to the stable enaminonitrile form. As a building block, it participates in a variety of multicomponent reactions (MCRs) and cyclocondensation reactions to afford fused bicyclic and polycyclic heterocycles, including pyridines, pyrimidines, and thiophene derivatives, depending on the co-reactants employed. These heterocyclic products are of considerable interest in medicinal chemistry as scaffolds for the development of bioactive molecules. Researchers also employ this compound in the synthesis of functionalized cyanopyridines and related analogs.
Handling, Storage, and Safety
As with all fine chemicals containing nitrile functionality, 2-Amino-1-cyclopentene-1-carbonitrile should be handled with appropriate personal protective equipment (PPE), including gloves, safety glasses, and a laboratory coat. Work should be conducted in a well-ventilated fume hood. The compound should be stored in a cool, dry place away from strong oxidizers, strong acids, and sources of ignition. Specific GHS hazard classifications and precautionary statements should be confirmed by consulting the current Safety Data Sheet (SDS) provided with the product. Users are advised to review the SDS before use and to comply with all applicable local regulations for the handling and disposal of nitrile-containing compounds.
Purity, Specifications, and Quality
Aladdin Scientific supplies 2-Amino-1-cyclopentene-1-carbonitrile (SKU: A183484) as a research-grade reagent. Typical characterization includes assessment by techniques such as NMR spectroscopy, GC or HPLC purity analysis, and melting point determination to confirm identity and purity. Researchers requiring specific purity thresholds or certificate of analysis (CoA) data should contact Aladdin Scientific's technical support or consult the product page for the most current lot-specific information. Bulk quantities and custom specifications may be available upon request.
Frequently asked questions
What is 2-Amino-1-cyclopentene-1-carbonitrile used for in research?
2-Amino-1-cyclopentene-1-carbonitrile is primarily used as a synthetic building block in organic and medicinal chemistry. It undergoes cyclocondensation and multicomponent reactions to produce a variety of nitrogen-containing heterocycles, including pyridine and pyrimidine derivatives, which serve as scaffolds for biologically active compounds.
How should 2-Amino-1-cyclopentene-1-carbonitrile be stored?
The compound should be stored in a cool, dry, and well-ventilated area, away from strong oxidizing agents, strong acids, and ignition sources. Always consult the current Safety Data Sheet (SDS) for lot-specific storage recommendations and hazard information before use.
What is the molecular formula and molecular weight of 2-Amino-1-cyclopentene-1-carbonitrile?
2-Amino-1-cyclopentene-1-carbonitrile has the molecular formula C6H8N2 and a molecular weight of approximately 108.14 g/mol. These values should be verified against the certificate of analysis for the specific lot purchased.
How is 2-Amino-1-cyclopentene-1-carbonitrile typically synthesized?
It is commonly prepared by reacting cyclopentanone with malononitrile under basic conditions via a Knoevenagel-type condensation, followed by tautomerization to yield the stable enaminonitrile product. Various bases and solvents can be employed depending on the desired reaction conditions.
Can I request a Certificate of Analysis (CoA) for this product?
Yes. A Certificate of Analysis for 2-Amino-1-cyclopentene-1-carbonitrile (SKU: A183484) can be obtained through the Aladdin Scientific product page or by contacting our customer support team with your lot number. The CoA includes identity, purity, and other quality data specific to your batch.
References
- General reference: Comprehensive Organic Transformations, Larock R.C. — for enaminonitrile chemistry. Specific citation to be verified.
- Knoevenagel condensation of cyclic ketones with malononitrile: general textbook reaction — specific primary literature citation needed.
- Aladdin Scientific product page for A183484. URL to be confirmed by editorial team.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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