Cas no 727737-00-0 (2-Pyridinecarbonitrile, 6-bromo-3-hydroxy-)

2-Pyridinecarbonitrile, 6-bromo-3-hydroxy-, is a brominated and hydroxylated pyridine derivative with significant utility in organic synthesis and pharmaceutical research. The presence of both bromo and hydroxy functional groups at the 6- and 3-positions, respectively, enhances its reactivity as a versatile intermediate for cross-coupling reactions, nucleophilic substitutions, and heterocyclic derivatization. The electron-withdrawing nitrile group further contributes to its utility in constructing complex molecular frameworks. This compound is particularly valued for its role in medicinal chemistry, where it serves as a precursor for bioactive molecules. Its well-defined structure and functional group compatibility make it a reliable building block for targeted synthetic applications.
2-Pyridinecarbonitrile, 6-bromo-3-hydroxy- structure
727737-00-0 structure
Product Name:2-Pyridinecarbonitrile, 6-bromo-3-hydroxy-
CAS No:727737-00-0
MF:C6H3BrN2O
MW:199.004820108414
CID:1757542
PubChem ID:23088708
Update Time:2025-05-26

2-Pyridinecarbonitrile, 6-bromo-3-hydroxy- Chemical and Physical Properties

Names and Identifiers

    • 2-Pyridinecarbonitrile, 6-bromo-3-hydroxy-
    • 6-bromo-3-hydroxypyridine-2-carbonitrile
    • CEB73700
    • DA-36448
    • SCHEMBL2946216
    • 727737-00-0
    • 6-Bromo-3-hydroxypicolinonitrile
    • LBUCAVGFSDCKGK-UHFFFAOYSA-N
    • SB53327
    • 6-bromo-2-cyano-3-hydroxypyridine
    • EN300-5251236
    • CS-0377319
    • Inchi: 1S/C6H3BrN2O/c7-6-2-1-5(10)4(3-8)9-6/h1-2,10H
    • InChI Key: LBUCAVGFSDCKGK-UHFFFAOYSA-N
    • SMILES: BrC1=CC=C(C(C#N)=N1)O

Computed Properties

  • Exact Mass: 197.94288g/mol
  • Monoisotopic Mass: 197.94288g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 0
  • Complexity: 164
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 2.1
  • Topological Polar Surface Area: 56.9?2

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Additional information on 2-Pyridinecarbonitrile, 6-bromo-3-hydroxy-

6-Bromo-3-Hydroxy-2-Pyridinecarbonitrile (CAS No: 727737-00-0)

6-Bromo-3-Hydroxy-2-Pyridinecarbonitrile, also known by its CAS number 727737-00-0, is a significant compound in the field of organic chemistry. This compound belongs to the pyridine derivatives family and is characterized by its unique structure, which includes a cyano group at the 2-position, a hydroxyl group at the 3-position, and a bromine atom at the 6-position of the pyridine ring. The combination of these functional groups makes it a versatile molecule with potential applications in various areas of science and technology.

The synthesis of 6-Bromo-3-Hydroxy-2-Pyridinecarbonitrile involves a series of well-established organic reactions. Typically, the starting material is a substituted pyridine derivative, which undergoes bromination, hydroxylation, and cyanation steps to achieve the desired product. These reactions are carefully optimized to ensure high yield and purity. The bromination step often utilizes bromine in the presence of a suitable catalyst, while the hydroxylation can be achieved through oxidation or substitution reactions. The introduction of the cyano group is typically carried out using cyanation reagents such as hydrogen cyanide or its equivalents under specific reaction conditions.

Recent studies have highlighted the potential of 6-Bromo-3-Hydroxy-2-Pyridinecarbonitrile in drug discovery and development. Its structure provides multiple sites for chemical modification, allowing researchers to explore its pharmacokinetic properties and biological activity. For instance, the hydroxyl group at the 3-position can serve as a site for glycosylation or other bioisosteric replacements, enhancing its solubility and bioavailability. Similarly, the bromine atom at the 6-position can be replaced with other substituents to modulate its pharmacodynamic properties.

In addition to its role in medicinal chemistry, 6-Bromo-3-Hydroxy-2-Pyridinecarbonitrile has shown promise in catalytic applications. The pyridine ring acts as a coordinating ligand, enabling it to bind with metal ions and form complexes that exhibit catalytic activity in various organic transformations. For example, palladium complexes derived from this compound have been reported to catalyze cross-coupling reactions with high efficiency and selectivity. This makes it a valuable tool in green chemistry and sustainable synthesis.

The compound's electronic properties also make it an interesting candidate for materials science applications. The conjugated system of the pyridine ring along with the electron-withdrawing cyano group imparts unique electronic characteristics to the molecule. These properties have been exploited in designing new materials for optoelectronic devices such as light-emitting diodes (LEDs) and photovoltaic cells. Recent research has focused on incorporating 6-Bromo-3-Hydroxy-2-Pyridinecarbonitrile into polymer frameworks to enhance their electronic performance.

From an environmental perspective, 6-Bromo-3-Hydroxy-2-Pyridinecarbonitrile has been studied for its biodegradability and eco-friendly synthesis routes. Researchers have developed methods that minimize waste generation and utilize renewable resources for its production. For instance, enzymatic catalysis has been employed to achieve selective transformations without generating harmful byproducts. These advancements align with global efforts to promote sustainable chemistry practices.

In conclusion, 6-Bromo-3-Hydroxy-2-Pyridinecarbonitrile (CAS No: 727737-00-0) is a multifaceted compound with diverse applications across various scientific disciplines. Its unique structure enables it to serve as a building block for drug development, catalysis, materials science, and eco-friendly chemical processes. As research continues to uncover new aspects of this compound's potential, it is poised to play an increasingly important role in advancing modern science and technology.

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