2-Amino-3,5-dichloropyridine
[CAS# 4214-74-8]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Chloropyridine
• Name: 2-Amino-3,5-dichloropyridine
• Synonyms: 3,5-Dichloro-2-pyridinamine
• Molecular Formula: C₅H₄Cl₂N₂
• Molecular Weight: 163.00
• CAS Registry Number: 4214-74-8
• EC Number: 224-143-5
• SMILES: C1=C(C=NC(=C1Cl)N)Cl

Properties

• Melting point: 79-83 °C
• Water solubility: insoluble

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H312-H315-H319-H332-H335
• Safety Statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362-P363-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

2-Amino-3,5-dichloropyridine is a chemical compound that has garnered attention for its utility in various fields, particularly in organic synthesis and medicinal chemistry. This compound, characterized by the presence of amino and dichloropyridine groups, offers unique properties that make it valuable in both research and practical applications.

The discovery of 2-amino-3,5-dichloropyridine is part of the broader effort to develop and explore new heterocyclic compounds with potential applications in diverse chemical processes. The synthesis of this compound typically involves the selective chlorination of pyridine derivatives followed by the introduction of an amino group. The precise conditions for these reactions are optimized to achieve high yields and purity of the final product. Characterization of 2-amino-3,5-dichloropyridine is usually performed using techniques such as nuclear magnetic resonance (NMR) spectroscopy, infrared (IR) spectroscopy, and mass spectrometry.

In organic synthesis, 2-amino-3,5-dichloropyridine is utilized as an intermediate in the preparation of various functionalized pyridine derivatives. Its unique structure allows for the introduction of additional functional groups, enabling the creation of complex molecules with specific properties. This versatility is particularly valuable in the synthesis of pharmaceuticals, agrochemicals, and materials science applications.

In medicinal chemistry, 2-amino-3,5-dichloropyridine has shown potential as a building block for the development of new therapeutic agents. The presence of both amino and chloropyridine groups can influence the biological activity of the compound, making it a candidate for further investigation as a lead compound in drug discovery. Its application in this field includes the synthesis of potential inhibitors or modulators of various biological targets.

The compound also plays a role in materials science, where its unique chemical properties are leveraged to create novel materials with desirable characteristics. For example, 2-amino-3,5-dichloropyridine can be used in the development of functionalized polymers or as a precursor for the synthesis of advanced materials with specific electronic or optical properties.

Handling and storage of 2-amino-3,5-dichloropyridine require standard safety precautions due to its chemical reactivity. The compound should be stored in a cool, dry place and handled with care to avoid exposure to moisture and air, which may affect its stability.

Future research on 2-amino-3,5-dichloropyridine may focus on expanding its applications and exploring its potential in new areas of chemistry. Investigations into its reactivity, biological activity, and utility in advanced materials could lead to further innovations and applications.

References

2008. Palladium-Catalyzed Indole and Azaindole Synthesis. Synthesis. DOI: 10.1055/s-0028-1083225

2009. Transition metal complexes of 2-amino-3,5-dihalopyridines. Dalton Transactions. DOI: 10.1039/b914392k

2024. Inhibition of DRP-1 mitochondrial mitophagy and fission by novel α-aminophosphonates bearing pyridine. BMC Chemistry. DOI: 10.1186/s13065-024-01268-2