3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-amine | CAS 83255-86-1

PRODUCT OVERVIEW

Chemical Name: 3-Bromo-1H-pyrazolo[3,4-d]pyrimidin-4-amine
CAS Number: 83255-86-1
Molecular Formula: C5H4BrN5
Molecular Weight: 214.03 g/mol
Synonyms:

• 3-Bromo-pyrazolo[3,4-d]pyrimidin-4-amine

• 4-Amino-3-bromopyrazolo[3,4-d]pyrimidine

3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-amine | CAS 83255-86-1 is a halogenated heterocyclic building block widely used in medicinal chemistry, agrochemical research, and drug discovery programs. Its bicyclic scaffold combines a pyrazole ring fused to a pyrimidine ring, making it a versatile intermediate for synthesizing biologically active compounds, kinase inhibitors, and other functionalized derivatives.

CHEMICAL STRUCTURE & PROPERTIES

The core structure of 3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-amine consists of a pyrazolo[3,4-d]pyrimidine ring system, which is known for its utility in modulating a range of biological targets due to favorable binding characteristics. Introducing a bromine at the 3-position provides a reactive handle for cross-coupling reactions such as Suzuki, Buchwald–Hartwig, and Stille couplings, greatly enhancing its utility in lead optimization.

Key Physicochemical Properties:

• Appearance: Off-white to light beige crystalline powder

• Solubility: Soluble in DMSO, DMF; moderate solubility in polar organic solvents

• Melting Point: Typically in the range of ~250–260 °C (literature dependent)

• Purity: Supplied with ≥98% purity (HPLC)

SYNTHETIC UTILITY & FUNCTIONALIZATION

One of the primary reasons researchers select 3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-amine is its high synthetic versatility. The bromine substituent at C3 serves as an excellent leaving group for a variety of transition-metal-catalyzed cross-coupling reactions. These reactions enable the construction of diverse C–C and C–N bonds, facilitating the rapid generation of analog libraries in medicinal chemistry:

• Suzuki–Miyaura Coupling: Introduce aryl or heteroaryl groups to the scaffold to explore SAR (structure–activity relationship) around the bicyclic core.

• Buchwald–Hartwig Amination: Install diverse amines or amide functionalities at the 3-position.

• Sonogashira Coupling: Attach alkynyl substituents for further functional elaboration.

• Negishi and Stille Cross-Couplings: Useful where alternate organometallic partners are desired.

In addition to cross-couplings, the 4-amino group provides a reactive nucleophilic site for acylation, sulfonylation, and urea/thiourea formation. This dual reactive framework (halide and amine) makes this compound an attractive intermediate for constructing complex heterocyclic architectures.

APPLICATIONS of 3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-amine | CAS 83255-86-1

1. Medicinal Chemistry

3-Bromo-1H-pyrazolo[3,4-d]pyrimidin-4-amine is frequently employed in the development of kinase inhibitors, especially targeting ATP-binding sites due to the planar bicyclic heterocycle’s ability to participate in hydrogen bonding and π–π stacking. Derivatives of this core have been investigated across oncology, inflammatory diseases, CNS disorders, and metabolic targets.

2. Agrochemical Discovery

The scaffold’s structural similarity to nucleobases enables interaction with biological targets in plant pests, fungi, and weeds. Functional derivatives have potential as herbicides, fungicides, or insect growth regulators pending appropriate optimization and safety evaluation.

3. Chemical Biology Probes

By incorporating fluorescent tags or affinity ligands onto the core via the 3-position, researchers can develop probes to interrogate biological pathways, enzyme function, or receptor engagement.

ANALYTICAL CHARACTERIZATION

ResolveMass supplies 3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-amine with full quality control documentation, including:

• HPLC Purity Report: ≥98%

• ^1H NMR / ^13C NMR Spectra: Clean spectra confirming structural integrity

• Mass Spectrometry: Molecular ion peak

• Elemental Analysis: Conformance with calculated values

These analytical data ensure confidence in downstream applications, whether for medicinal chemistry, screening campaigns, or synthetic methodologies.

SAFETY & HANDLING

Hazard Classification:
3-Bromo-1H-pyrazolo[3,4-d]pyrimidin-4-amine should be handled in accordance with standard laboratory safety practices. Brominated heterocycles may be irritants and should not be inhaled, ingested, or permitted to contact skin or eyes.

Precautions:

• Use personal protective equipment (PPE): gloves, goggles, lab coat

• Work in a well-ventilated area or fume hood

• Avoid generating dust

• Store away from strong oxidizers and moisture

First Aid Measures:

• Skin Contact: Rinse immediately with plenty of water; seek medical advice if irritation persists

• Eye Contact: Flush cautiously with water for several minutes

• Inhalation: Move to fresh air and consult a physician if symptoms occur

A Safety Data Sheet (SDS) is available upon request to ensure compliance with regulatory and institutional safety protocols.

STORAGE & STABILITY

• Recommended Storage Conditions: Cool, dry, and well-ventilated environment

• Temperature: Ambient (15–25 °C) or refrigerated (2–8 °C) for extended stability

• Container: Tightly closed, inert atmosphere if possible

• Shelf Life: Stable under recommended storage; refer to lot-specific data

Proper storage significantly enhances long-term stability, minimizing potential degradation that could affect research outcomes.

ORDERING & AVAILABILITY

ResolveMass Laboratories Inc. offers 3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-amine in a variety of package sizes to suit both discovery and scale-up needs. Each lot is tested and supported with detailed analytical documentation.

For pricing, lead times, and custom quantity requests, please contact our sales team at sales@resolvemass.ca or through our online inquiry form.

SUMMARY

3-Bromo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (CAS 83255-86-1) is a high-value synthetic intermediate in heterocyclic chemistry. Its combination of a halogenated bicyclic core and an amine functional group makes it exceptionally useful for cross-coupling reactions and building complex molecules in medicinal and agrochemical R&D. With robust analytical documentation and safe handling protocols, ResolveMass provides a reliable source of this key building block for your next research project.