6-Chloro-1H-pyrazolo[3,4-b]pyrazine
[CAS# 1260664-81-0]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrazines
• Name: 6-Chloro-1H-pyrazolo[3,4-b]pyrazine
• Molecular Formula: C₅H₃ClN₄
• Molecular Weight: 154.56
• CAS Registry Number: 1260664-81-0
• EC Number: 813-010-2
• SMILES: C1=C(N=C2C(=N1)C=NN2)Cl

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H312-H315-H319-H335
• Precautionary 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
Acute toxicity	Acute Tox.	4	H312

Discovory and Applicatios

The discovery of 6-chloro-1H-pyrazolo[3,4-b]pyrazine stems from advances in heterocyclic chemistry and the synthesis of fused pyrazole-pyrazine ring systems. Researchers initially explored the cyclization reaction of appropriate precursor molecules containing pyrazole and pyrazine moieties under controlled conditions. The synthesis generally involves condensing suitable starting materials that can undergo cyclization to form the fused pyrazolo[3,4-b]pyrazine structure. The key steps in the synthesis include the selection of precursor molecules with reactive functional groups capable of cyclization, such as amino and halogen, under specific temperature and solvent conditions to ensure the formation of the fused ring system. For example, the introduction of a chlorine atom at the 6-position of the pyrazolo[3,4-b]pyrazine structure requires a suitable chlorinating agent and reaction conditions. The synthesized compounds are purified using chromatographic techniques and characterized using spectroscopic methods such as NMR, IR, and mass spectrometry to confirm their chemical structure and purity.

The molecular structure of 6-chloro-1H-pyrazolo[3,4-b]pyrazine has a fused pyrazole-pyrazine ring system and a chlorine atom. This structure confers specific chemical properties such as moderate solubility in organic solvents, stability under standard laboratory conditions, and the potential for further functionalization through organic synthesis. The fused ring structure enhances its stability, making it a valuable scaffold for molecular design in drug discovery and materials science.

In pharmaceuticals, 6-chloro-1H-pyrazolo[3,4-b]pyrazine is a key intermediate in the synthesis of bioactive compounds. Its structural features allow for modifications to enhance drug efficacy, improve pharmacokinetic properties, and optimize interactions with biological targets. Researchers are exploring derivatives of this compound for the treatment of a variety of diseases, including cancer, inflammation, and neurological disorders.

In materials science, 6-chloro-1H-pyrazolo[3,4-b]pyrazine is used as a building block for the synthesis of functional materials and polymers. Its fused ring structure and reactive functional groups facilitate polymerization reactions and the creation of materials with tailored properties such as thermal stability, conductivity, and optical properties. Applications include the development of specialty coatings, electronic materials, and sensors for various industrial applications.

Derivatives of 6-chloro-1H-pyrazolo[3,4-b]pyrazine are used in agrochemicals as herbicides, fungicides, and insecticides. These compounds have selective toxicity against pests and weeds, which can help develop effective crop protection strategies and reduce environmental impact. Their stability and efficacy make them valuable tools in modern agricultural practices, supporting sustainable agriculture and food security.

Further research on 6-chloro-1H-pyrazolo[3,4-b]pyrazine aims to expand its applications in nanotechnology, catalysis, and biomedical engineering. Research focuses on optimizing synthetic methods, exploring novel derivatives, and studying its interaction mechanisms with biological systems. These advances are expected to discover new applications and enhance the impact of this compound in various scientific disciplines.