Cas no 66092-63-5 (6-Bromo-4-nitronicotinic acid)

6-Bromo-4-nitronicotinic acid is a heterocyclic compound featuring a bromo-substituted pyridine core with a nitro group and carboxylic acid functionality. This structure makes it a versatile intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and specialty chemicals. The presence of both electron-withdrawing (nitro) and electron-donating (carboxylic acid) groups enhances its reactivity in nucleophilic and electrophilic substitution reactions. Its high purity and stability under standard conditions ensure reliable performance in multi-step synthetic pathways. The compound is particularly valuable in medicinal chemistry for constructing complex molecules due to its functional group compatibility and potential for further derivatization.
6-Bromo-4-nitronicotinic acid structure
6-Bromo-4-nitronicotinic acid structure
Product Name:6-Bromo-4-nitronicotinic acid
CAS No:66092-63-5
MF:C6H3BrN2O4
MW:247.003020524979
MDL:MFCD25965927
CID:3166589
PubChem ID:85938173
Update Time:2025-06-26

6-Bromo-4-nitronicotinic acid Chemical and Physical Properties

Names and Identifiers

    • 66092-63-5
    • 6-Bromo-4-nitronicotinic acid
    • 3-Pyridinecarboxylic acid, 6-bromo-4-nitro-
    • DXCCKVXDMGBPDN-UHFFFAOYSA-N
    • W12053
    • SCHEMBL16333727
    • DS-013015
    • 6-Bromo-4-nitronicotinicacid
    • MFCD25965927
    • AS-78463
    • 6-bromo-4-nitropyridine-3-carboxylic acid
    • MDL: MFCD25965927
    • Inchi: 1S/C6H3BrN2O4/c7-5-1-4(9(12)13)3(2-8-5)6(10)11/h1-2H,(H,10,11)
    • InChI Key: DXCCKVXDMGBPDN-UHFFFAOYSA-N
    • SMILES: BrC1=CC(=C(C(=O)O)C=N1)[N+](=O)[O-]

Computed Properties

  • Exact Mass: 245.92762g/mol
  • Monoisotopic Mass: 245.92762g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 2
  • Complexity: 229
  • 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: 1.2
  • Topological Polar Surface Area: 96?2

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Additional information on 6-Bromo-4-nitronicotinic acid

Introduction to 6-Bromo-4-nitronicotinic Acid (CAS No: 66092-63-5)

6-Bromo-4-nitronicotinic acid, identified by its Chemical Abstracts Service (CAS) number 66092-63-5, is a specialized organic compound that has garnered significant attention in the field of medicinal chemistry and pharmaceutical research. This compound belongs to the nicotinic acid derivatives, a class of molecules known for their diverse biological activities and therapeutic potential. The structural features of 6-Bromo-4-nitronicotinic acid, particularly the presence of both bromine and nitro substituents, make it a versatile intermediate in the synthesis of more complex pharmacological agents.

Thenicotinic acid derivatives have been extensively studied due to their ability to interact with various biological targets, including enzymes and receptors. Among these derivatives, 6-Bromo-4-nitronicotinic acid stands out due to its unique reactivity and potential applications in drug development. The bromine atom at the 6-position and the nitro group at the 4-position introduce specific electronic and steric properties that can be exploited in medicinal chemistry strategies.

In recent years, there has been a surge in research focused on developing novel therapeutic agents targeting neurological disorders, cardiovascular diseases, and metabolic syndromes. 6-Bromo-4-nitronicotinic acid has emerged as a key intermediate in the synthesis of molecules that modulate key signaling pathways involved in these conditions. For instance, studies have demonstrated its utility in generating analogs that exhibit inhibitory effects on enzymes such as xanthine oxidase and lipoxygenase, which are implicated in inflammation and oxidative stress.

One of the most compelling aspects of 6-Bromo-4-nitronicotinic acid is its role in the development of kinase inhibitors. Kinases are enzymes that play a critical role in cell signaling, and their dysregulation is associated with numerous diseases, including cancer. The bromine substituent in 6-Bromo-4-nitronicotinic acid allows for further functionalization via cross-coupling reactions, such as Suzuki-Miyaura or Buchwald-Hartwig couplings, enabling the construction of complex kinase inhibitors. These inhibitors have shown promise in preclinical studies as potential treatments for various malignancies.

Moreover, the nitro group at the 4-position of 6-Bromo-4-nitronicotinic acid serves as a versatile handle for chemical manipulation. Reductive amination or diazotization followed by coupling reactions can yield derivatives with enhanced binding affinity to biological targets. Such modifications have been employed to develop novel antimicrobial agents, which are increasingly important due to the rise of drug-resistant pathogens.

The pharmaceutical industry has also explored the use of 6-Bromo-4-nitronicotinic acid in the synthesis of antiviral compounds. The structural motif present in this compound has been incorporated into molecules designed to inhibit viral proteases and polymerases. Preliminary findings suggest that certain derivatives exhibit significant antiviral activity against RNA viruses, making them attractive candidates for further development.

In addition to its applications in drug discovery, 6-Bromo-4-nitronicotinic acid has found utility in materials science. Its ability to undergo selective functionalization makes it a valuable precursor for designing organic semiconductors and luminescent materials. These materials are being explored for applications in optoelectronics, such as organic light-emitting diodes (OLEDs) and photovoltaic devices.

The synthesis of 6-Bromo-4-nitronicotinic acid itself is an intricate process that requires careful optimization to ensure high yield and purity. Traditional synthetic routes often involve multi-step sequences starting from commercially available nicotinic acid derivatives. Recent advancements in synthetic methodologies have enabled more efficient pathways, including catalytic bromination and nitration techniques that minimize byproduct formation.

One notable improvement has been the adoption of flow chemistry techniques for the preparation of 6-Bromo-4-nitronicotinic acid. Flow systems allow for better control over reaction conditions, leading to improved reproducibility and scalability. This approach has been particularly beneficial in industrial settings where large-scale production is required.

The safety profile of 6-Bromo-4-nitronicotinic acid is another critical consideration. While it is not classified as a hazardous material under standard regulations, proper handling procedures must be followed to prevent exposure during synthesis and handling. Personal protective equipment (PPE), such as gloves and lab coats, should be worn at all times when working with this compound.

In conclusion,6-Bromo-4-nitronicotinic acid (CAS No: 66092-63-5) is a multifaceted compound with significant potential in pharmaceutical research and industrial applications. Its unique structural features make it an invaluable intermediate for synthesizing biologically active molecules targeting various diseases. As research continues to uncover new therapeutic possibilities,6-Bromo-4-nitronicotinic acid will undoubtedly remain at the forefront of medicinal chemistry innovation.

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