5-Amino-2-methyloxazole-4-carbonitrile: Properties & Applications
5-Amino-2-methyloxazole-4-carbonitrile: Properties & Applications
5-Amino-2-methyloxazole-4-carbonitrile is a functionalized oxazole heterocycle bearing both an amino group and a nitrile substituent, making it a versatile bifunctional building block for medicinal chemistry and the synthesis of complex nitrogen-containing scaffolds.
- Chemical Name
- 5-Amino-2-methyloxazole-4-carbonitrile
- SKU
- A193650
- Core Heterocycle
- 1,3-Oxazole
- Key Functional Groups
- Primary amine (–NH₂), nitrile (–CN), methyl (–CH₃)
- Molecular Formula
- C₅H₅N₃O
- Supplier
- Aladdin Scientific
Chemical Identity and Structure
5-Amino-2-methyloxazole-4-carbonitrile (SKU A193650) is a member of the 1,3-oxazole family of aromatic five-membered heterocycles. The oxazole ring contains both oxygen and nitrogen atoms at the 1- and 3-positions respectively, conferring significant aromatic stability and unique electronic character.
The compound carries three key substituents: a methyl group at the 2-position, a nitrile (cyano) group at the 4-position, and a primary amino group at the 5-position. This combination of electron-donating (–NH₂) and electron-withdrawing (–CN) groups on the same ring creates a push-pull electronic environment that enhances the reactivity of the molecule toward a broad range of synthetic transformations.
The molecular formula is C₅H₅N₃O, reflecting the compact yet information-rich architecture typical of privileged heterocyclic scaffolds used in drug discovery and materials science.
Reactivity and Synthetic Utility
The bifunctional nature of 5-Amino-2-methyloxazole-4-carbonitrile makes it an exceptionally useful building block in multi-step synthesis. The primary amino group at the 5-position can participate in acylation, sulfonylation, reductive amination, condensation with aldehydes or ketones, and formation of ureas or guanidines, enabling rapid diversification of the molecular scaffold.
The nitrile group at the 4-position serves as a handle for further elaboration: it can be hydrolyzed to the corresponding carboxylic acid or amide, reduced to an amine, or converted to tetrazoles via [3+2] cycloaddition with azides—a reaction of particular interest in medicinal chemistry for bioisosteric replacement of carboxylic acids.
The methyl group at the 2-position provides modest steric and electronic modulation of the ring, and can in principle be functionalized under appropriate oxidative conditions. Together, these features make A193650 a highly versatile intermediate for the construction of fused heterocyclic systems, including oxazolopyrimidines, oxazolotriazines, and related drug-like scaffolds.
Applications in Medicinal Chemistry and Drug Discovery
Oxazole-containing compounds represent an important class of pharmacophores found in numerous bioactive natural products and approved pharmaceuticals. The aminooxazole carbonitrile scaffold of A193650 is particularly attractive as a starting point for the synthesis of kinase inhibitors, antimicrobial agents, and anti-inflammatory compounds, where the oxazole ring frequently contributes to target binding through hydrogen-bond donor/acceptor interactions and π-stacking with aromatic residues.
The amino group provides a direct hydrogen-bond donor capability, while the ring nitrogen and the nitrile group offer hydrogen-bond acceptor sites. This multi-point interaction potential is advantageous in the design of ligands for a range of biological targets. Researchers engaged in fragment-based drug discovery may find A193650 a useful fragment with drug-like physicochemical properties, including low molecular weight and appropriate polarity.
Additionally, the compound can serve as a precursor to fluorescent dyes, agrochemical intermediates, and functional materials, broadening its utility beyond pharmaceutical research.
Handling, Storage, and Safety Considerations
As with all fine chemicals containing a nitrile functional group, appropriate laboratory safety precautions should be observed when handling 5-Amino-2-methyloxazole-4-carbonitrile. Nitrile-containing compounds may release toxic hydrogen cyanide upon decomposition; therefore, work should be conducted in a well-ventilated fume hood, and contact with strong acids or bases should be avoided unless required by the experimental protocol.
The compound should be stored in a cool, dry, and well-ventilated location, away from moisture, heat, and incompatible materials such as strong oxidizing agents. The container should be kept tightly sealed to prevent moisture uptake and degradation of the solid material. Recommended storage temperature and specific hazard classification should be confirmed against the product's Safety Data Sheet (SDS) provided by Aladdin Scientific.
Researchers should consult the current SDS for comprehensive hazard information, first-aid measures, and disposal guidelines in compliance with local regulations before using this reagent.
Frequently asked questions
What is the molecular formula of 5-Amino-2-methyloxazole-4-carbonitrile?
The molecular formula of 5-Amino-2-methyloxazole-4-carbonitrile is C₅H₅N₃O. The structure comprises a 1,3-oxazole ring substituted with a methyl group at position 2, a cyano group at position 4, and a primary amino group at position 5.
What types of reactions can the amino group of this compound undergo?
The primary amino group at the 5-position of 5-Amino-2-methyloxazole-4-carbonitrile is amenable to a wide range of transformations, including acylation, sulfonylation, reductive amination, imine/enamine formation with carbonyl compounds, and condensation reactions to form ureas, thioureas, and guanidines. These reactions allow rapid structural diversification for library synthesis and SAR studies.
How should 5-Amino-2-methyloxazole-4-carbonitrile (A193650) be stored?
The compound should be stored in a tightly sealed container in a cool, dry, and well-ventilated area, away from moisture, heat sources, and strong oxidizing agents. For specific temperature recommendations and full hazard information, researchers should refer to the Safety Data Sheet (SDS) available from Aladdin Scientific.
Is 5-Amino-2-methyloxazole-4-carbonitrile suitable for fragment-based drug discovery?
Yes, the compound's low molecular weight, multiple hydrogen-bond interaction sites (amino group as donor; ring nitrogen and nitrile as acceptors), and synthetic versatility make it an attractive fragment for fragment-based drug discovery (FBDD) campaigns. Its bifunctional character enables straightforward elaboration into more complex drug-like molecules.
References
- Joule, J. A.; Mills, K. Heterocyclic Chemistry, 5th ed.; Wiley-Blackwell: Oxford, 2010. (General reference for oxazole chemistry and reactivity.)
- Fringuelli, F.; Taticchi, A. The Diels-Alder Reaction: Selected Practical Methods; Wiley: Chichester, 2002. (Background on heterocyclic building blocks in synthesis.)
- Aladdin Scientific. Product page for 5-Amino-2-methyloxazole-4-carbonitrile, SKU A193650. (Primary source for product identity and availability.)
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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