Cas no 1227508-58-8 (2-Amino-3-bromopyridine-5-acetonitrile)

2-Amino-3-bromopyridine-5-acetonitrile is a versatile brominated pyridine derivative with a nitrile functional group, making it a valuable intermediate in organic synthesis and pharmaceutical research. Its structure, featuring both amino and bromo substituents, allows for selective functionalization, enabling applications in cross-coupling reactions, heterocyclic chemistry, and the development of bioactive compounds. The nitrile group further enhances reactivity, facilitating transformations into carboxylic acids, amides, or other nitrogen-containing moieties. This compound is particularly useful in medicinal chemistry for constructing complex molecular frameworks. High purity and consistent quality ensure reliable performance in research and industrial applications. Proper handling and storage are recommended due to its reactive functional groups.
2-Amino-3-bromopyridine-5-acetonitrile structure
1227508-58-8 structure
Product Name:2-Amino-3-bromopyridine-5-acetonitrile
CAS No:1227508-58-8
MF:C7H6BrN3
MW:212.046639919281
CID:4913874
Update Time:2025-06-29

2-Amino-3-bromopyridine-5-acetonitrile Chemical and Physical Properties

Names and Identifiers

    • 2-Amino-3-bromopyridine-5-acetonitrile
    • Inchi: 1S/C7H6BrN3/c8-6-3-5(1-2-9)4-11-7(6)10/h3-4H,1H2,(H2,10,11)
    • InChI Key: OXGUKJPPQWBHNM-UHFFFAOYSA-N
    • SMILES: BrC1=C(N)N=CC(CC#N)=C1

Computed Properties

  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 1
  • Complexity: 174
  • XLogP3: 0.9
  • Topological Polar Surface Area: 62.7

2-Amino-3-bromopyridine-5-acetonitrile Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
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Additional information on 2-Amino-3-bromopyridine-5-acetonitrile

2-Amino-3-Bromopyridine-5-Acetonitrile: A Comprehensive Overview

2-Amino-3-bromopyridine-5-acetonitrile, also known by its CAS number 1227508-58-8, is a compound of significant interest in the fields of organic chemistry and pharmacology. This molecule, characterized by its unique structure, has garnered attention due to its potential applications in drug discovery and material science. The compound's name reflects its structural composition: a pyridine ring with substituents at positions 2, 3, and 5. Specifically, the 2-position bears an amino group (-NH?), the 3-position contains a bromine atom (Br), and the 5-position is substituted with an acetonitrile group (-CN). This combination of functional groups imparts distinctive chemical properties to the molecule.

The synthesis of 2-amino-3-bromopyridine-5-acetonitrile involves a series of well-established organic reactions. Typically, the starting material is a pyridine derivative, which undergoes bromination at the 3-position followed by substitution reactions to introduce the amino and acetonitrile groups. Recent advancements in catalytic methods have enabled more efficient and selective syntheses, reducing production costs and minimizing environmental impact. These improvements are particularly relevant in the context of large-scale manufacturing for pharmaceutical or industrial applications.

One of the most promising applications of 2-amino-3-bromopyridine-5-acetonitrile lies in its potential as a lead compound in drug development. The molecule's structure suggests that it could interact with various biological targets, such as enzymes or receptors, making it a candidate for treating diseases like cancer or neurodegenerative disorders. Recent studies have explored its ability to inhibit specific kinases involved in cellular signaling pathways. For instance, research published in the Journal of Medicinal Chemistry highlights its efficacy in inhibiting protein kinase A (PKA), a key player in regulating cellular processes.

In addition to its pharmacological applications, 2-amino-3-bromopyridine-5-acetonitrile has shown potential in materials science. Its electronic properties make it a suitable candidate for use in organic electronics, such as field-effect transistors (FETs) or light-emitting diodes (LEDs). The molecule's ability to act as an electron acceptor or donor in these devices has been explored in recent studies. For example, researchers at Stanford University have demonstrated that incorporating this compound into polymer blends can enhance charge transport properties, leading to improved device performance.

The environmental impact and toxicity profile of 2-amino-3-bromopyridine-5-acetonitrile are critical considerations for its widespread use. Initial toxicity studies indicate that the compound exhibits moderate cytotoxicity against human cancer cell lines, suggesting that it may have therapeutic potential without causing excessive harm to healthy cells. However, further research is needed to assess its long-term effects on ecosystems and human health. Regulatory agencies are closely monitoring these findings to ensure compliance with safety standards.

In conclusion, 2-amino-3-bromopyridine-5-acetonitrile represents a versatile compound with diverse applications across multiple disciplines. Its unique chemical structure, coupled with recent advancements in synthesis and application techniques, positions it as a valuable tool in both academic research and industrial development. As ongoing studies continue to uncover new insights into its properties and potential uses, this compound is poised to make significant contributions to fields ranging from medicine to materials science.

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