5-tert-Butyl-1,3,4-oxadiazol-2-amine: Properties & Lab Guide
5-tert-Butyl-1,3,4-oxadiazol-2-amine: Properties & Lab Guide
5-tert-Butyl-1,3,4-oxadiazol-2-amine is a five-membered nitrogen- and oxygen-containing heterocyclic building block widely employed in medicinal chemistry and organic synthesis for the construction of bioactive molecules and functional materials.
- Chemical Name
- 5-tert-Butyl-1,3,4-oxadiazol-2-amine
- SKU
- T177215
- Core Scaffold
- 1,3,4-Oxadiazole ring with a primary amine at C-2 and a tert-butyl group at C-5
- Typical Application
- Intermediate for synthesis of pharmacologically active oxadiazole derivatives
- Functional Groups
- Primary amine (–NH₂) and 1,3,4-oxadiazole heterocycle
- Supplier
- Aladdin Scientific
Chemical Identity and Structure
5-tert-Butyl-1,3,4-oxadiazol-2-amine belongs to the 1,3,4-oxadiazole family of five-membered aromatic heterocycles that contain one oxygen and two nitrogen atoms. The compound features a primary amino group (–NH₂) at the 2-position and a sterically hindered tert-butyl substituent at the 5-position of the oxadiazole ring. This combination confers a degree of lipophilicity from the tert-butyl moiety alongside the nucleophilic reactivity of the exocyclic amine, making the molecule a versatile bifunctional building block.
The 1,3,4-oxadiazole core is a π-deficient aromatic ring system known for metabolic stability, hydrogen-bond-accepting capacity, and favorable physicochemical properties in drug-like molecules. The tert-butyl group at C-5 increases the steric bulk around the ring and modulates electronic density, which can influence the reactivity of the C-2 amine in downstream coupling reactions.
Handling, Safety, and Storage Guidelines
As with all reactive amine-containing heterocyclic compounds, standard laboratory safety precautions should be observed when working with 5-tert-Butyl-1,3,4-oxadiazol-2-amine. Personnel should wear appropriate personal protective equipment (PPE) including chemically resistant gloves, safety glasses, and a laboratory coat. Operations that may generate dust or aerosols should be conducted in a well-ventilated fume hood.
The compound should be stored in a tightly sealed container under cool, dry conditions away from strong oxidizing agents, strong acids, and strong bases, which could react with the amino group or the oxadiazole ring. Refer to the Safety Data Sheet (SDS) provided by Aladdin Scientific for authoritative hazard classification, first-aid measures, and disposal guidance before use. In the absence of specific stability data, storage at 2–8 °C under an inert atmosphere (nitrogen or argon) is a prudent precaution to minimize oxidative degradation of the amine functionality.
Research Applications and Synthetic Utility
The 1,3,4-oxadiazole scaffold is well-represented in medicinal chemistry literature as a privileged heterocyclic motif associated with a broad spectrum of biological activities including antimicrobial, anti-inflammatory, anticancer, and antidiabetic properties. 5-tert-Butyl-1,3,4-oxadiazol-2-amine provides a ready-made, pre-formed oxadiazole ring carrying both a reactive amine handle for further functionalization and a lipophilic tert-butyl group for tuning pharmacokinetic parameters.
In synthetic contexts, the primary amine at C-2 can be acylated, sulfonylated, alkylated, or engaged in reductive amination and condensation reactions to produce urea, thiourea, amide, sulfonamide, and imine derivatives. These transformations enable rapid diversification of the scaffold for structure–activity relationship (SAR) studies. The compound is also a candidate building block in fragment-based drug discovery (FBDD) programs where its compact, drug-like framework can serve as a fragment hit for optimization.
Quality, Purity, and Ordering Information
Aladdin Scientific supplies 5-tert-Butyl-1,3,4-oxadiazol-2-amine under catalog number T177215. Researchers should request the certificate of analysis (CoA) for each lot to confirm identity (e.g., by NMR, MS) and purity before use in sensitive assays or as a reference standard. Purity specifications and available pack sizes can be confirmed through the Aladdin Scientific product page or by contacting technical support.
For procurement teams, the compound is available through the standard Aladdin Scientific ordering channels. Volume pricing, custom quantities, and delivery lead times can be discussed with the Aladdin sales team. Proper import/export documentation should be prepared in accordance with local regulations for specialty chemical shipments.
Frequently asked questions
What is 5-tert-Butyl-1,3,4-oxadiazol-2-amine used for in research?
It is primarily used as a heterocyclic building block in medicinal chemistry for constructing ureas, amides, sulfonamides, and other derivatives via reactions at its primary amine group. The pre-formed 1,3,4-oxadiazole ring saves synthetic steps and the tert-butyl substituent helps tune lipophilicity of the final target molecules.
How should 5-tert-Butyl-1,3,4-oxadiazol-2-amine be stored to maintain stability?
In the absence of compound-specific validated stability data, it is advisable to store the material in a sealed container at 2–8 °C under an inert atmosphere (nitrogen or argon), away from moisture, oxidizing agents, and strong acids or bases. Always consult the Aladdin Scientific SDS and lot-specific CoA for authoritative guidance.
Can the amino group of this compound be selectively functionalized?
Yes, the exocyclic primary amine at C-2 is the principal reactive site and can be selectively acylated, sulfonylated, or alkylated under standard conditions to generate diverse derivative libraries. The aromatic oxadiazole ring is generally stable under mild functionalization conditions, enabling chemoselectivity at the amine.
Where can I find the purity specification and certificate of analysis for SKU T177215?
The purity specification and lot-specific certificate of analysis (CoA) for T177215 are available on the Aladdin Scientific product page or upon request from Aladdin customer support. It is recommended to review the CoA before use in critical experiments.
References
- Kaur, R. et al. 1,3,4-Oxadiazole: a versatile scaffold in drug discovery. Mini-Reviews in Medicinal Chemistry. (General review of oxadiazole pharmacology — specific volume and page unverified.)
- Aladdin Scientific. Product listing: 5-tert-Butyl-1,3,4-oxadiazol-2-amine, SKU T177215. Aladdin Scientific official catalog.
- Meanwell, N.A. Synopsis of some recent tactical application of bioisosteres in drug design. Journal of Medicinal Chemistry, 2011. (Oxadiazole as amide bioisostere context — specific page numbers unverified.)
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
危险品化学品经营许可证（带存储）