6-Cyclopropylpyridin-3-amine: Properties & Lab FAQ
6-Cyclopropylpyridin-3-amine: Properties & Lab FAQ
6-Cyclopropylpyridin-3-amine is a versatile aminopyridine building block featuring a cyclopropyl substituent at the 6-position, widely used as a synthetic intermediate in medicinal chemistry and drug discovery research.
- Chemical Name
- 6-Cyclopropylpyridin-3-amine
- SKU / Product Code
- C732573
- Compound Class
- Aminopyridine heterocyclic building block
- Primary Application
- Synthetic intermediate in medicinal chemistry and drug discovery
- Supplier
- Aladdin Scientific
- Functional Groups
- Primary aromatic amine (-NH2) on pyridine ring; cyclopropyl ring at C-6 position
What Is 6-Cyclopropylpyridin-3-amine?
6-Cyclopropylpyridin-3-amine is a substituted aminopyridine in which a cyclopropyl group occupies the 6-position of the pyridine ring and a primary amine (–NH2) is located at the 3-position (meta to N-1). This combination of a basic nitrogen in the ring, a reactive exocyclic amine, and a strained cyclopropyl moiety makes the compound a valuable synthetic building block.
The cyclopropyl group is frequently employed in drug design to improve metabolic stability, modulate lipophilicity, and introduce conformational rigidity compared with an analogous methyl or ethyl substituent. The free amine at C-3 provides a convenient handle for further functionalization via acylation, sulfonylation, reductive amination, or coupling reactions, enabling rapid elaboration of the pyridine scaffold into more complex drug-like molecules.
Handling, Storage, and Safety
As with most primary aromatic amines, 6-Cyclopropylpyridin-3-amine should be handled with appropriate personal protective equipment including nitrile gloves, safety glasses, and a laboratory coat. Operations generating dust or aerosols should be performed in a fume hood.
Storage recommendations (general guidance for aminopyridine building blocks):
- Store in a tightly sealed container away from light, moisture, and incompatible oxidizing agents.
- Refrigerated storage (2–8 °C) or cool, dry conditions are typically recommended to preserve purity over extended periods.
- Allow the container to equilibrate to room temperature before opening to minimize condensation on the solid material.
Consult the product-specific Safety Data Sheet (SDS) available on the Aladdin Scientific website for authoritative hazard classification, first-aid measures, and disposal guidance before use.
Research and Synthetic Applications
6-Cyclopropylpyridin-3-amine finds utility across several areas of research and synthesis:
- Drug discovery intermediates: The compound serves as a core scaffold for the preparation of kinase inhibitors, GPCRs modulators, and other bioactive small molecules. The 3-amino group can be converted to amides, ureas, sulfonamides, or used in Buchwald–Hartwig cross-coupling reactions to access arylamino derivatives.
- Fragment-based drug design (FBDD): Its compact, polar structure with defined exit vectors makes it suitable as a fragment or fragment-linker in FBDD campaigns.
- Heterocyclic chemistry: The amine can participate in condensation reactions to construct fused ring systems such as imidazopyridines, pyrrolopyridines, or quinoline analogues.
- Agrochemical research: Cyclopropyl-substituted pyridine amines are also explored as intermediates in the synthesis of herbicide and fungicide candidates.
Researchers are encouraged to review current literature for specific reaction conditions and yields when using this building block in novel synthetic routes.
Ordering, Availability, and Quality
6-Cyclopropylpyridin-3-amine is available from Aladdin Scientific under SKU C732573. When placing an order, customers should consider the following:
- Pack sizes: Multiple gram-scale pack sizes may be available to suit both early-stage discovery (small quantities) and scale-up needs. Contact Aladdin Scientific for bulk pricing and availability.
- Purity: Aladdin Scientific reagents are subject to quality-control testing. Refer to the Certificate of Analysis (CoA) provided with each lot for confirmed purity data, analytical methods used (e.g., HPLC, NMR), and lot-specific results.
- Lead time: Standard catalog items are typically dispatched promptly; availability is subject to stock levels. For time-sensitive projects, confirm stock status with the sales team before ordering.
- Custom synthesis: If larger quantities or specific purity grades are required, Aladdin Scientific may offer custom synthesis options—contact customer service for a quotation.
Frequently Asked Questions Summary
The following section compiles the most common technical and procurement questions received about 6-Cyclopropylpyridin-3-amine. For questions not addressed here, please contact Aladdin Scientific technical support or consult the product page for the latest documentation including the SDS and CoA.
Frequently asked questions
What is the molecular structure of 6-Cyclopropylpyridin-3-amine and how does the cyclopropyl group affect its properties?
6-Cyclopropylpyridin-3-amine consists of a pyridine ring bearing a primary amino group (–NH2) at the 3-position and a cyclopropyl group at the 6-position. The cyclopropyl substituent introduces conformational rigidity and mild electron donation to the ring system while improving metabolic stability relative to linear alkyl groups. These combined electronic and steric effects make it attractive for designing drug candidates with improved pharmacokinetic profiles.
How should 6-Cyclopropylpyridin-3-amine be stored to maintain purity?
The compound should be stored in a tightly sealed container under cool, dry, and dark conditions; refrigerated storage at 2–8 °C is generally advisable for long-term stability of aminopyridine building blocks. Moisture and prolonged exposure to air or light should be avoided to prevent degradation of the primary amine functionality. Always consult the product-specific CoA and SDS from Aladdin Scientific for lot-confirmed storage recommendations.
What synthetic transformations can be performed using the amine group of 6-Cyclopropylpyridin-3-amine?
The primary aromatic amine at C-3 is a versatile reactive handle that can undergo acylation to form amides, reaction with sulfonyl chlorides to give sulfonamides, condensation with carbonyl compounds for imine or reductive amination products, and transition-metal-catalyzed Buchwald–Hartwig coupling to install aryl or heteroaryl groups. It can also participate in cyclization reactions to build fused heterocyclic scaffolds such as imidazopyridines or benzimidazole analogues, expanding the chemical space accessible from this single building block.
How do I obtain a Certificate of Analysis (CoA) or Safety Data Sheet (SDS) for SKU C732573?
The Certificate of Analysis and Safety Data Sheet for 6-Cyclopropylpyridin-3-amine (SKU C732573) are available directly from the Aladdin Scientific product page. Enter the lot number printed on your product label to download the lot-specific CoA. For SDS documents or if you require assistance, contact Aladdin Scientific customer service via the website or by email.
Is 6-Cyclopropylpyridin-3-amine suitable for use as a fragment in fragment-based drug discovery?
Yes, the compound's low molecular weight, defined polarity from both the pyridine nitrogen and the exocyclic amine, and the vector provided by the cyclopropyl group at C-6 make it a reasonable starting fragment or fragment-linker for fragment-based drug discovery (FBDD) programs. Its two distinct functional handles (ring nitrogen and exocyclic NH2) allow growth in multiple directions, which is advantageous in fragment elaboration strategies. Researchers should assess its physicochemical properties against their project-specific fragment criteria.
References
- Aladdin Scientific product page for 6-Cyclopropylpyridin-3-amine, SKU C732573.
- General reference: Lovering, F.; Bikker, J.; Humblet, C. Escape from Flatland: Increasing Saturation as an Approach to Improving Clinical Success. J. Med. Chem. 2009, 52, 6752–6756. doi:10.1021/jm901241e
- Ritchie, T. J.; Macdonald, S. J. F. The impact of aromatic ring count on compound developability—are too many rings a liability in drug design? Drug Discov. Today 2009, 14, 1011–1020. doi:10.1016/j.drudis.2009.07.014
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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