3,5-Dichloropyridin-4-amine
[CAS# 228809-78-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Aminopyridine
• Name: 3,5-Dichloropyridin-4-amine
• Synonyms: 4-ADCP
• Molecular Formula: C₅H₄Cl₂N₂
• Molecular Weight: 163.00
• CAS Registry Number: 228809-78-7
• EC Number: 245-304-6
• SMILES: C1=C(C(=C(C=N1)Cl)N)Cl

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07 Danger
• Hazard Statements: H300-H302-H310-H315-H318-H319-H330-H335
• Precautionary Statements: P260-P261-P262-P264-P264+P265-P270-P271-P280-P284-P301+P316-P301+P317-P302+P352-P304+P340-P305+P351+P338-P305+P354+P338-P316-P317-P319-P320-P321-P330-P332+P317-P337+P317-P361+P364-P362+P364-P403+P233-P405-P501

Discovory and Applicatios

3,5-Dichloropyridin-4-amine is an organic compound widely used in the field of chemical synthesis and pharmaceutical development. Structurally, it consists of a pyridine ring substituted with two chlorine atoms at positions 3 and 5, and an amino group at position 4. This specific arrangement of functional groups gives the compound unique reactivity, making it a valuable intermediate in the synthesis of more complex molecules.

The discovery and use of 3,5-dichloropyridin-4-amine are closely linked to efforts in drug development, where pyridine derivatives have shown significant potential in the creation of biologically active compounds. The introduction of chlorine atoms at the 3 and 5 positions on the pyridine ring enhances the compound’s electrophilicity, making it more reactive in substitution reactions. The amino group at position 4 further adds versatility, allowing the compound to participate in a variety of synthetic pathways, including nucleophilic substitution and coupling reactions.

In pharmaceutical research, 3,5-dichloropyridin-4-amine has been utilized as a key intermediate in the development of kinase inhibitors, antiviral agents, and other therapeutic compounds. Its ability to act as a building block for these molecules has made it important in medicinal chemistry, where the modification of the pyridine ring often leads to new therapeutic candidates with improved efficacy and selectivity. For example, the compound’s chlorinated positions can be leveraged in structure-activity relationship (SAR) studies to optimize drug-like properties, including potency and bioavailability.

Beyond drug discovery, 3,5-dichloropyridin-4-amine also finds applications in the agricultural industry, where pyridine-based compounds are used in the development of herbicides and pesticides. Its reactive nature allows it to be incorporated into molecules designed to inhibit the growth of weeds or pests, providing a foundation for the creation of more effective agrochemical products.

The broad applicability of 3,5-dichloropyridin-4-amine in both pharmaceutical and agricultural chemistry highlights its significance as a versatile synthetic intermediate. Its ability to undergo various reactions with precision enables chemists to construct a wide range of functionalized molecules, contributing to advancements in multiple fields.

References

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