2-(4-Methylpiperazin-1-yl)acetonitrile: Properties & Lab Uses
2-(4-Methylpiperazin-1-yl)acetonitrile: Properties & Lab Uses
2-(4-Methylpiperazin-1-yl)acetonitrile is a piperazine-based nitrile building block widely employed in medicinal chemistry and organic synthesis as a versatile intermediate for constructing pharmacologically relevant heterocyclic scaffolds.
- Chemical Name
- 2-(4-Methylpiperazin-1-yl)acetonitrile
- SKU
- A724847
- Molecular Formula
- C7H13N3
- Functional Groups
- Tertiary amine (piperazine N-methyl) and nitrile (–CN)
- Primary Application
- Pharmaceutical intermediate and synthetic building block
- Compound Class
- Piperazine-substituted acetonitrile; heterocyclic nitrile
Chemical Identity and Structure
2-(4-Methylpiperazin-1-yl)acetonitrile (SKU: A724847) is an organic compound bearing two distinct reactive motifs: a piperazine ring with a terminal N-methyl group, and an acetonitrile (–CH2CN) unit attached at the other piperazine nitrogen. Its molecular formula is C7H13N3, giving a molecular weight of approximately 139.20 g/mol. The molecule is classified as a heterocyclic nitrile and belongs to the broader family of piperazine derivatives that are extensively exploited in drug discovery programs.
The coexistence of a basic, nucleophilic tertiary amine nitrogen and an electrophilic nitrile carbon within the same molecule makes this compound a bifunctional synthon. The nitrile group can undergo hydrolysis to carboxylic acids or amides, reduction to primary amines, or cycloaddition reactions, while the methylpiperazine fragment confers aqueous solubility and modulates the physicochemical profile of downstream products.
Synthesis and Reactivity in Organic Chemistry
The compound is typically prepared by N-alkylation of 1-methylpiperazine with chloroacetonitrile or bromoacetonitrile under mild basic conditions, a straightforward one-step reaction that proceeds in good yield. This synthetic accessibility makes it an attractive starting material for library synthesis in high-throughput medicinal chemistry campaigns.
Key transformations enabled by 2-(4-Methylpiperazin-1-yl)acetonitrile include: (1) Nitrile hydrolysis to yield 2-(4-methylpiperazin-1-yl)acetic acid, a carboxylic acid handle useful for amide coupling; (2) Reduction with LiAlH4 or BH3 to afford the corresponding primary amine; (3) Cycloaddition or cyclization reactions exploiting the activated methylene adjacent to nitrogen to build five- or six-membered heterocycles; (4) Mannich-type reactions leveraging the alpha-amino nitrile character of the molecule. These reaction pathways underline the compound's value as a versatile synthon in building structurally diverse compound libraries.
Applications in Medicinal Chemistry and Drug Discovery
Piperazine-containing scaffolds are among the most frequently encountered structural motifs in approved pharmaceuticals, valued for their ability to improve aqueous solubility, modulate basicity, and engage in productive interactions with biological targets. 2-(4-Methylpiperazin-1-yl)acetonitrile serves as a direct precursor to such scaffolds, allowing medicinal chemists to rapidly introduce the pharmacophoric methylpiperazine unit while simultaneously providing a handle—the nitrile—for further diversification.
The compound finds application in the preparation of kinase inhibitor candidates, CNS-active agents, and anti-infective leads, where the methylpiperazine moiety is known to contribute favorable ADMET properties including enhanced membrane permeability and metabolic stability relative to unsubstituted piperazines. Researchers also use this building block in fragment-based drug design, where compact, bifunctional fragments are assembled into lead molecules.
Handling, Storage, and Safety Considerations
As with all nitrile-containing compounds, 2-(4-Methylpiperazin-1-yl)acetonitrile should be handled with appropriate personal protective equipment (PPE), including chemical-resistant gloves, safety glasses, and a laboratory coat. Operations generating dust or aerosols should be conducted in a well-ventilated fume hood. While the compound is not classified as a highly toxic nitrile such as hydrogen cyanide, nitrile functional groups can release cyanide ion under certain degradation conditions, warranting careful handling.
For storage, the compound should be kept in a tightly sealed container, protected from moisture and heat, and stored at room temperature or as specified on the Certificate of Analysis (CoA). Compatibility with strong oxidizers, strong acids, and strong bases should be evaluated before combining with other reagents. Users should consult the Safety Data Sheet (SDS) supplied by Aladdin Scientific prior to use for comprehensive hazard, first-aid, and disposal information.
Frequently asked questions
What is 2-(4-Methylpiperazin-1-yl)acetonitrile used for in research?
It is primarily used as a bifunctional synthetic building block in medicinal chemistry and pharmaceutical research. The nitrile group enables downstream transformations such as hydrolysis, reduction, and cyclization, while the N-methylpiperazine moiety introduces a pharmacophoric fragment known to improve aqueous solubility and ADMET properties in drug candidates.
How should 2-(4-Methylpiperazin-1-yl)acetonitrile be stored to maintain stability?
The compound should be stored in a tightly sealed container, away from moisture, heat, and incompatible materials such as strong acids, bases, or oxidizers. Storage at room temperature under dry conditions is generally recommended; consult the Certificate of Analysis (CoA) from Aladdin Scientific for product-specific storage conditions.
What safety precautions are required when handling this nitrile compound?
Users should wear appropriate PPE including chemical-resistant gloves, safety glasses, and a lab coat. All manipulations should be performed in a well-ventilated fume hood. Before use, the Safety Data Sheet (SDS) provided by Aladdin Scientific must be reviewed for complete hazard, first-aid, and waste disposal guidance, as nitrile-containing compounds can release cyanide ion under degradation conditions.
What is the molecular formula and molecular weight of 2-(4-Methylpiperazin-1-yl)acetonitrile?
The molecular formula is C7H13N3 and the molecular weight is approximately 139.20 g/mol. Researchers should verify the exact purity and identity data against the Certificate of Analysis supplied with each lot from Aladdin Scientific (SKU: A724847).
References
- March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. General reference for nitrile reactivity and N-alkylation of piperazines.
- Vital statistics on piperazine-containing drugs: Pharmacophore analysis of approved pharmaceuticals. General textbook-level reference on piperazine scaffolds in drug design.
- Aladdin Scientific. Product page for 2-(4-Methylpiperazin-1-yl)acetonitrile, SKU A724847. Safety Data Sheet and Certificate of Analysis available on request.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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