5-Phenyl-1H-pyrazol-4-amine: Properties, Handling & Lab Use
5-Phenyl-1H-pyrazol-4-amine: Properties, Handling & Lab Use
5-Phenyl-1H-pyrazol-4-amine is a bicyclic heterocyclic compound featuring a pyrazole ring substituted with an amino group at the 4-position and a phenyl group at the 5-position, making it a versatile building block for medicinal chemistry and heterocyclic synthesis.
- IUPAC Name
- 5-Phenyl-1H-pyrazol-4-amine
- CAS Number
- To be confirmed (review required)
- Molecular Formula
- C₉H₉N₃
- Molecular Weight
- 159.19 g/mol
- Core Scaffold
- 1H-Pyrazole with 4-amino and 5-phenyl substituents
- SKU (Aladdin)
- P726690
- Typical Application
- Intermediate in heterocyclic and medicinal chemistry synthesis
Chemical Structure and Key Properties
5-Phenyl-1H-pyrazol-4-amine (Aladdin SKU: P726690) belongs to the aminopyrazole class of heterocyclic compounds. The molecule comprises a five-membered pyrazole ring containing two adjacent nitrogen atoms, bearing a primary amino (–NH₂) group at C-4 and a phenyl ring at C-5. This substitution pattern confers the compound with both hydrogen-bond donor (N–H of the NH₂ and the ring N–H) and hydrogen-bond acceptor (pyrazole nitrogens, amino group) capabilities, which are pharmacologically relevant features.
The molecular formula is C₉H₉N₃ and the calculated molecular weight is approximately 159.19 g/mol. The compound is expected to be a solid at room temperature. Specific melting point, purity specification, and exact CAS number should be confirmed against the current Aladdin certificate of analysis for lot P726690 before use.
Solubility and Storage Guidelines
Aminopyrazole derivatives are generally soluble in polar aprotic solvents such as dimethyl sulfoxide (DMSO) and dimethylformamide (DMF), as well as in lower alcohols such as methanol and ethanol. Aqueous solubility may be limited at neutral pH but can improve under acidic conditions due to protonation of the amino or pyrazole nitrogen. Researchers should prepare stock solutions fresh or validate stability if storing dissolved aliquots.
For long-term storage of the neat solid, keep the material in a tightly sealed container under cool, dry conditions (typically 2–8 °C or as specified on the product label), protected from moisture and light. Always refer to the Aladdin product specification sheet and Safety Data Sheet (SDS) for the definitive storage recommendation for lot P726690.
Laboratory Applications and Synthetic Utility
5-Phenyl-1H-pyrazol-4-amine is valued as a synthetic intermediate and building block in medicinal chemistry. The aminopyrazole scaffold is found in numerous biologically active molecules, including kinase inhibitors and anti-inflammatory agents, owing to the scaffold's ability to form key hydrogen-bond interactions within enzyme active sites.
In practice, the free amino group at C-4 can be engaged in a wide variety of transformations: acylation to form amides, condensation with carbonyl compounds to give Schiff bases or cyclized heterocycles, and coupling reactions to elaborate the molecular framework. The 5-phenyl substituent provides additional opportunities for electrophilic or cross-coupling reactions if functionalized analogues are desired. Researchers in drug discovery, agrochemical development, and materials science may find this compound useful as a precursor to more complex pyrazole-containing targets.
Safe Handling and Regulatory Considerations
As with all fine chemical reagents, appropriate personal protective equipment (PPE) should be used when handling 5-Phenyl-1H-pyrazol-4-amine. This includes laboratory coat, nitrile gloves, and safety eyewear. Operations that may generate dust or aerosols should be conducted in a fume hood. Avoid ingestion, inhalation, and skin or eye contact.
Specific hazard classifications, GHS pictograms, first-aid measures, and disposal instructions are detailed in the Aladdin Safety Data Sheet for product P726690. Always consult the SDS before first use. Waste containing this compound should be disposed of in accordance with local institutional and governmental regulations for chemical waste.
Frequently asked questions
What solvents are recommended for dissolving 5-Phenyl-1H-pyrazol-4-amine?
DMSO and DMF are generally effective solvents for aminopyrazole compounds. Alcohols such as methanol and ethanol may also be suitable. Aqueous solubility is typically low at neutral pH but may improve under acidic conditions. Always verify solubility experimentally with your specific lot.
How should 5-Phenyl-1H-pyrazol-4-amine (P726690) be stored to maintain stability?
The solid reagent should be stored in a tightly closed container at cool, dry conditions (typically 2–8 °C) and protected from light and moisture. Refer to the Aladdin SDS and certificate of analysis for the definitive storage conditions applicable to your lot.
What chemical reactions can be performed using the amino group of 5-Phenyl-1H-pyrazol-4-amine?
The primary amino group at C-4 can undergo acylation (forming amides), condensation with aldehydes or ketones (forming imines or cyclized heterocycles), and reductive amination, among other transformations. These reactions make the compound a versatile scaffold for constructing more complex drug-like molecules.
Is 5-Phenyl-1H-pyrazol-4-amine suitable for use as a kinase inhibitor building block?
The aminopyrazole motif is a well-recognized pharmacophore in kinase inhibitor design due to its capacity to mimic the adenine moiety of ATP and form hydrogen bonds in the hinge region of kinase active sites. 5-Phenyl-1H-pyrazol-4-amine may serve as a useful starting point; however, specific biological activity data for this compound should be confirmed with primary literature or assay data before drawing conclusions.
References
- Aladdin Scientific Product Page: 5-Phenyl-1H-pyrazol-4-amine, SKU P726690. Aladdin Scientific (accessed 2024).
- General reference on aminopyrazole pharmacophores in kinase inhibitor design — specific citation to be identified and verified by subject-matter expert.
- Joule, J. A.; Mills, K. Heterocyclic Chemistry, 5th ed.; Wiley-Blackwell: Oxford, 2010. (General textbook-level reference for pyrazole chemistry.)
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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