1-Benzyl-1H-indazol-5-ylamine: Properties, Handling & Research Use
1-Benzyl-1H-indazol-5-ylamine: Properties, Handling & Research Use
1-Benzyl-1H-indazol-5-ylamine is a synthetic heterocyclic primary amine featuring an indazole core N-substituted with a benzyl group at position 1 and a free amino group at position 5, making it a versatile building block for medicinal chemistry and drug discovery research.
- CAS / SKU
- SKU B192227; CAS number to be confirmed — see review flag
- Molecular Formula
- C14H13N3 (MW ≈ 223.27 g/mol) — verify against CoA
- Functional Groups
- Primary aromatic amine (–NH2) at C-5; N-benzyl substituent at N-1 of the indazole ring
- Key Application
- Intermediate and building block in synthesis of indazole-based bioactive compounds and kinase-targeting small molecules
- Recommended Storage
- Store in a cool, dry, well-ventilated area away from light; confirm exact conditions on product CoA
- Purity
- Confirm purity grade and specification from current CoA supplied with product (B192227)
Chemical Identity and Structure
1-Benzyl-1H-indazol-5-ylamine belongs to the indazole family of bicyclic nitrogen heterocycles, comprising a fused benzene and pyrazole ring system. In this compound, the nitrogen at position 1 of the indazole ring bears a benzyl (phenylmethyl) substituent, which distinguishes it from unsubstituted or N2-substituted analogues. The primary amine at C-5 provides a reactive handle for further functionalization, including acylation, sulfonylation, reductive amination, and coupling reactions.
The indazole scaffold is recognized in medicinal chemistry for its bioisosteric relationships with indole and benzimidazole, and its presence in approved pharmaceuticals and clinical candidates targeting kinases, phosphodiesterases, and other enzyme classes. The N-benzyl group at position 1 directs regioselectivity during synthesis and modulates the electronic density of the ring, influencing the reactivity of the C-5 amine and the overall physicochemical profile of the molecule.
Physicochemical Properties and Handling
Based on its molecular structure (C14H13N3, MW ≈ 223.27 g/mol), 1-Benzyl-1H-indazol-5-ylamine is expected to be a solid at room temperature. The compound is likely to exhibit moderate solubility in polar aprotic solvents such as DMSO and DMF, and limited solubility in water, consistent with the lipophilic benzyl group and aromatic ring system. Researchers should consult the Certificate of Analysis (CoA) supplied with SKU B192227 for confirmed melting point, appearance, purity, and solubility data.
When preparing stock solutions, dissolution in DMSO is generally recommended as a starting point for biological assay work; confirm compatibility with the assay system before use. For synthetic applications, common solvents such as dichloromethane, THF, acetonitrile, and ethanol may be appropriate depending on the reaction. All physicochemical values cited here are estimated from structural analogy and should be verified against the product CoA.
Research Applications
The primary amine at C-5 of 1-Benzyl-1H-indazol-5-ylamine makes it a versatile synthetic intermediate. It can be employed as a building block in the preparation of amides, ureas, sulfonamides, and Schiff bases, enabling the rapid construction of compound libraries for structure–activity relationship (SAR) studies. Indazole-containing compounds have been investigated as scaffolds for kinase inhibitors, anti-inflammatory agents, and anticancer candidates in the published literature.
In fragment-based and diversity-oriented synthesis, N-protected or N-functionalized indazolyl amines such as this compound serve as privileged structural motifs. The N-1 benzyl group can also be removed under appropriate hydrogenolysis conditions to yield the N-1 unsubstituted indazol-5-amine if required for downstream chemistry. Researchers should evaluate the compound's suitability for each specific application through in-house validation.
Storage, Stability, and Safety Guidelines
As an aromatic primary amine, 1-Benzyl-1H-indazol-5-ylamine should be handled with appropriate precautions. Aromatic amines as a chemical class may present hazards including skin and eye irritation, and potential sensitization; always consult the Safety Data Sheet (SDS) for SKU B192227 before use. Use appropriate personal protective equipment (PPE) including nitrile gloves, lab coat, and safety glasses. Conduct all handling in a well-ventilated fume hood.
For storage, keep the compound in a tightly sealed container in a cool, dry, and dark environment. Protect from moisture, heat, and incompatible oxidizing agents. Long-term stability should be confirmed by periodic re-analysis or by reference to the expiry date stated on the product label and CoA. Dispose of waste material in accordance with local institutional and governmental regulations for organic chemical waste.
Ordering, Specifications, and Quality Assurance
1-Benzyl-1H-indazol-5-ylamine is available from Aladdin Scientific under SKU B192227. Researchers and procurement personnel should request the current Certificate of Analysis (CoA) at the time of ordering to confirm lot-specific purity, appearance, and analytical data (typically including HPLC purity, NMR confirmation, and MS data). Bulk quantities and custom pack sizes may be available upon request; contact Aladdin Scientific customer service for pricing and availability.
Aladdin Scientific's quality assurance process includes identity confirmation and purity testing prior to release. For regulated research environments, additional documentation such as specification sheets or material safety information can be requested. All orders are subject to Aladdin Scientific's standard terms and conditions regarding shipping, returns, and payment.
Frequently asked questions
What solvents are recommended for dissolving 1-Benzyl-1H-indazol-5-ylamine?
DMSO is generally a good first choice for biological assay stock solutions due to its broad solvating power. For synthetic work, solvents such as DMF, dichloromethane, THF, or acetonitrile are typically suitable. Always consult the CoA for confirmed solubility data and verify compatibility with your specific application.
Can the N-1 benzyl group in 1-Benzyl-1H-indazol-5-ylamine be removed to access the N-unsubstituted indazolamine?
Yes, N-benzyl groups on indazoles can in principle be removed by catalytic hydrogenolysis (e.g., Pd/C, H2 in a suitable solvent). However, the selectivity and yield depend on the specific substrate and reaction conditions. Experimental optimization and literature precedent for closely related indazole substrates should be consulted before applying this strategy.
What safety precautions should be taken when handling 1-Benzyl-1H-indazol-5-ylamine?
As an aromatic amine, this compound should be handled with care. Always consult the SDS for SKU B192227 before use. Wear appropriate PPE including nitrile gloves, lab coat, and safety glasses, and work in a well-ventilated fume hood. Avoid skin contact, inhalation, and ingestion, and dispose of waste in accordance with institutional and regulatory guidelines.
How should 1-Benzyl-1H-indazol-5-ylamine be stored to maintain its integrity?
Store the compound in a tightly sealed container in a cool, dry, and dark location, away from moisture, heat, and oxidizing agents. Refer to the product label and CoA for the specific recommended storage temperature and shelf life for each lot.
What are the main research applications of 1-Benzyl-1H-indazol-5-ylamine?
This compound serves primarily as a synthetic building block for the preparation of indazole-based bioactive molecules. Its reactive primary amine allows formation of amides, ureas, sulfonamides, and imines for SAR studies. The indazole scaffold is relevant to kinase inhibitor research, anti-inflammatory compound development, and other areas of medicinal chemistry.
References
- Aladdin Scientific product page and Certificate of Analysis for 1-Benzyl-1H-indazol-5-ylamine, SKU B192227. Aladdin Scientific.
- Comprehensive Medicinal Chemistry contributions on indazole as a privileged scaffold in drug discovery — general textbook-level reference; specific citation to be confirmed.
- March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 7th ed. Smith, M. B. Wiley, 2013 — general reference for amine reactivity and N-benzyl deprotection chemistry.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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