6-Chloro-1H-pyrazolo[3,4-d]pyrimidine
[CAS# 23002-51-9]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Chloropyrimidine
• Name: 6-Chloro-1H-pyrazolo[3,4-d]pyrimidine
• Molecular Formula: C₅H₃ClN₄
• Molecular Weight: 154.56
• CAS Registry Number: 23002-51-9
• EC Number: 822-382-5
• SMILES: C1=C2C=NNC2=NC(=N1)Cl

Properties

• Density: 1.7±0.1 g/cm³ Calc.^*
• Boiling point: 305.2±24.0 °C 760 mmHg (Calc.)^*
• Flash point: 167.0±8.5 °C (Calc.)^*
• Index of refraction: 1.74 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H312-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

6-Chloro-1H-pyrazolo[3,4-d]pyrimidine is a heterocyclic compound that features a pyrazole ring fused to a pyrimidine ring, making it part of the class of pyrazolopyrimidines. This compound has gained attention due to its unique structural features, which contribute to its reactivity and biological activity. The chloro group at the 6-position on the pyrazole ring adds an electrophilic functional group that enhances the reactivity of the compound in various chemical reactions.

The synthesis of 6-chloro-1H-pyrazolo[3,4-d]pyrimidine typically involves the condensation of a suitable pyrazole derivative with a pyrimidine precursor. Several synthetic methods have been developed to prepare this compound, often using halogenated starting materials and appropriate reaction conditions to selectively introduce the chloro group at the desired position on the pyrazole ring.

In terms of applications, 6-chloro-1H-pyrazolo[3,4-d]pyrimidine serves as an important intermediate in the synthesis of various bioactive molecules, particularly in the pharmaceutical industry. The presence of the chloro group, as well as the fused heterocyclic structure, makes this compound a valuable building block for the design of kinase inhibitors, which are critical in the development of targeted cancer therapies. The compound’s pyrazolopyrimidine core structure is similar to other bioactive molecules that have shown promising results in the inhibition of key enzymes involved in cellular signaling pathways.

Moreover, 6-chloro-1H-pyrazolo[3,4-d]pyrimidine has been investigated for its potential role in the treatment of diseases associated with dysregulated kinase activity. Its ability to interact with the ATP-binding sites of various kinases allows it to function as a selective inhibitor. As a result, compounds based on this structure have been explored for use in treating a range of diseases, including cancers, inflammatory disorders, and autoimmune diseases. The chloro substitution on the pyrazole ring plays a critical role in enhancing the compound’s binding affinity and selectivity for specific protein targets.

Additionally, 6-chloro-1H-pyrazolo[3,4-d]pyrimidine is used in the development of chemical probes and research tools for studying the biological functions of certain enzymes and proteins. By modifying the pyrazolopyrimidine core or attaching different functional groups to the molecule, researchers can create analogs that are tailored to interact with specific biomolecular targets. This approach is particularly useful in the field of drug discovery, where understanding the mechanism of action of a potential drug is crucial for its development into a therapeutic agent.

In the field of materials science, the pyrazolopyrimidine core structure of 6-chloro-1H-pyrazolo[3,4-d]pyrimidine can also be leveraged for the synthesis of novel organic materials. These materials can have applications in electronics, such as organic semiconductors and photovoltaic devices, due to the unique electronic properties imparted by the fused heterocyclic rings.

The physical properties of 6-chloro-1H-pyrazolo[3,4-d]pyrimidine include its solubility in common organic solvents, such as DMSO and dimethylformamide, which facilitates its use in various chemical and biological applications. The chloro group on the pyrazole ring may also provide some steric protection, allowing for selective functionalization at other positions on the molecule, further expanding its utility in chemical synthesis.

In conclusion, 6-chloro-1H-pyrazolo[3,4-d]pyrimidine is a significant compound in organic and medicinal chemistry due to its structural features and biological activity. Its role as an intermediate in the synthesis of kinase inhibitors and other bioactive molecules positions it as a valuable building block in drug discovery. Moreover, its potential applications in materials science and research tool development further enhance its importance in various fields of study. The chloro substitution on the pyrazole ring enhances the compound’s reactivity and selectivity, making it a versatile and important chemical for both pharmaceutical and materials applications.

References

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