4-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-3-yl)phenol | CAS 1293915-57-7

PRODUCT OVERVIEW

4-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-3-yl)phenol | CAS 1293915-57-7  is a heterocyclic aromatic intermediate consisting of a phenolic ring bonded to a substituted pyrazolo[3,4-d]pyrimidine core. Its molecular formula is C₁₁H₉N₅O and molecular weight is 227.22 g/mol, making it a relatively low-molecular-weight heterocycle valued in medicinal chemistry research and fine chemical synthesis.

The structure combines a phenol functional group with a nitrogen-rich bicyclic ring system (pyrazolo[3,4-d]pyrimidine), which provides a scaffold often used in designing bioactive compounds due to its potential for hydrogen bonding and π-stacking interactions.

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CHEMICAL IDENTIFICATION

• IUPAC Name: 4-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-3-yl)phenol

• CAS Number: 1293915-57-7

• Synonyms: Phenol, 4-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-; 4-(4-Aminopyrazolo[3,4-d]pyrimidin-3-yl)phenol

• Molecular Formula: C₁₁H₉N₅O

• Molecular Weight: 227.23 g/mol

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PHYSICAL & PREDICTED PROPERTIES of 4-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-3-yl)phenol | CAS 1293915-57-7

While experimental data for many heterocyclic intermediates are often limited, predicted physicochemical properties provide useful guidance:

• Boiling Point: ~572 °C (predicted)

• Density: ~1.54 g/cm³ (predicted)

• pKa (Phenolic H): ~8.4 (predicted)

These predicted values are consistent with similar phenolic heterocyclic compounds, where the phenol group imparts slightly acidic character and the pyrazolopyrimidine core contributes to aromatic stability and higher melting/boiling characteristics.

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SYNTHETIC USES & APPLICATIONS

Chemical Intermediate in Drug Discovery

4-(4-Amino-1H-pyrazolo[3,4-d]pyrimidin-3-yl)phenol is most commonly used as a building block and intermediate in the synthesis of bioactive heterocyclic compounds. The pyrazolo[3,4-d]pyrimidine scaffold is widely studied in medicinal chemistry because it can interact with biological targets such as kinases, GPCRs, and various enzymes. These interactions make derivatives potentially valuable for oncology, anti-inflammatory, and CNS targets. Research publications exploring similarly substituted pyrazolo[3,4-d]pyrimidines demonstrate their importance in designing anticancer agents and other therapeutic leads.

Versatile Functional Handles

• The phenolic hydroxyl group provides a site for further functionalization, including etherification, ester formation, and cross-coupling reactions.

• The amino group on the heterocyclic core allows for amide bond formation or incorporation into larger scaffolds. These functional groups make the compound suitable as an intermediate in fragment-based drug design and structure-activity relationship (SAR) studies.

Research & Development Tool

Given the structural complexity and the presence of heteroatoms, this compound is commonly used in R&D laboratories for multi-step synthesis and method development, especially in academic settings focusing on novel heterocyclic chemotypes.

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CHEMICAL REACTIVITY

The reactivity of 4-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-3-yl)phenol is dominated by:

• Phenol reactivity: Electrophilic aromatic substitution and protection/deprotection strategies are widely applied.

• Amino group chemistry: Typical of primary amines—nucleophilic acyl substitution, reductive amination, and heterocycle formation.

• Heterocyclic core: Offers multiple positions amenable to substitution for SAR exploration.

Such reactivity enables the compound to serve as a versatile node in synthetic schemes for complex targets.

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HANDLING, STORAGE & SAFETY

As with most fine chemicals and heterocyclic intermediates:

• Handle under appropriate safety protocols, including gloves, goggles, and lab coat.

• Avoid ingestion, inhalation, or skin contact.

• Store in a cool, dry place, away from incompatible substances. Detailed Safety Data Sheets (SDS) should always be consulted for hazard and first-aid measures before use.

Since this compound is provided for research or manufacturing use, and not for direct pharmaceutical application, it should be used strictly in accordance with applicable regulatory and institutional guidelines.

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QUALITY & PURITY

ResolveMass Laboratories Inc. offers this compound with high purity (typically ≥95%, depending on specification) suitable for research, analytical, and synthetic applications. Thorough QC testing, including HPLC, NMR, and MS verification, ensures product integrity and reproducibility in downstream applications.

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CONCLUSION

4-(4-Amino-1H-pyrazolo[3,4-d]pyrimidin-3-yl)phenol (CAS 1293915-57-7) is an important heterocyclic intermediate, widely used in medicinal chemistry and synthetic research. Its combination of functional groups and heterocyclic architecture makes it a valuable building block for a range of bioactive molecules and advanced chemical synthesis.