Cas no 1806291-13-3 (3,6-Dimethoxy-2-nitropyridine)

3,6-Dimethoxy-2-nitropyridine is a nitropyridine derivative characterized by its methoxy substituents at the 3- and 6-positions and a nitro group at the 2-position. This compound serves as a versatile intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and fine chemicals. Its electron-withdrawing nitro group and electron-donating methoxy groups contribute to its reactivity in nucleophilic substitution and reduction reactions. The compound’s well-defined structure and stability under standard conditions make it a reliable building block for heterocyclic chemistry. It is commonly utilized in the development of complex molecules requiring regioselective functionalization. Proper handling and storage are recommended due to its potential sensitivity to light and moisture.
3,6-Dimethoxy-2-nitropyridine structure
3,6-Dimethoxy-2-nitropyridine structure
Product Name:3,6-Dimethoxy-2-nitropyridine
CAS No:1806291-13-3
MF:C7H8N2O4
MW:184.149421691895
CID:4905013
Update Time:2025-10-19

3,6-Dimethoxy-2-nitropyridine Chemical and Physical Properties

Names and Identifiers

    • 3,6-Dimethoxy-2-nitropyridine
    • Inchi: 1S/C7H8N2O4/c1-12-5-3-4-6(13-2)8-7(5)9(10)11/h3-4H,1-2H3
    • InChI Key: RZJWWRZNSUOJSL-UHFFFAOYSA-N
    • SMILES: O(C)C1=CC=C(N=C1[N+](=O)[O-])OC

Computed Properties

  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 2
  • Complexity: 182
  • XLogP3: 1.3
  • Topological Polar Surface Area: 77.2

3,6-Dimethoxy-2-nitropyridine Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
Alichem
A029006948-250mg
3,6-Dimethoxy-2-nitropyridine
1806291-13-3 95%
250mg
$960.40 2022-03-31
Alichem
A029006948-500mg
3,6-Dimethoxy-2-nitropyridine
1806291-13-3 95%
500mg
$1,836.65 2022-03-31
Alichem
A029006948-1g
3,6-Dimethoxy-2-nitropyridine
1806291-13-3 95%
1g
$2,750.25 2022-03-31

Additional information on 3,6-Dimethoxy-2-nitropyridine

Introduction to 3,6-Dimethoxy-2-nitropyridine (CAS No. 1806291-13-3)

3,6-Dimethoxy-2-nitropyridine, identified by its Chemical Abstracts Service (CAS) number 1806291-13-3, is a heterocyclic organic compound that has garnered significant attention in the field of chemical biology and pharmaceutical research. This compound belongs to the pyridine family, a class of nitrogen-containing heterocycles that are widely recognized for their diverse biological activities and utility in medicinal chemistry. The structural features of 3,6-Dimethoxy-2-nitropyridine, particularly the presence of methoxy and nitro substituents, contribute to its unique chemical properties and make it a valuable scaffold for the development of novel therapeutic agents.

The molecular structure of 3,6-Dimethoxy-2-nitropyridine consists of a six-membered aromatic ring containing nitrogen, with methoxy groups attached at the 3rd and 6th positions and a nitro group at the 2nd position. This arrangement imparts a balance of electron-donating and electron-withdrawing effects, which can influence its reactivity and interactions with biological targets. The nitro group, in particular, is known to be a versatile functional handle in organic synthesis, enabling further derivatization through reduction or nucleophilic substitution reactions.

In recent years, 3,6-Dimethoxy-2-nitropyridine has been explored as a key intermediate in the synthesis of various biologically active compounds. Its pyridine core is a common motif in many pharmaceuticals, including antiviral, antibacterial, and anticancer agents. The methoxy substituents enhance lipophilicity, while the nitro group can be used to modulate pharmacokinetic properties. This makes 3,6-Dimethoxy-2-nitropyridine a promising building block for drug discovery programs targeting neurological disorders, inflammation, and metabolic diseases.

One of the most compelling aspects of 3,6-Dimethoxy-2-nitropyridine is its potential in medicinal chemistry due to its ability to serve as a precursor for more complex molecules. Researchers have leveraged its structural framework to develop inhibitors of enzymes involved in cancer progression and inflammatory pathways. For instance, derivatives of this compound have shown promise in preclinical studies as modulators of Janus kinases (JAKs), which are implicated in autoimmune diseases such as rheumatoid arthritis. The nitro group can be selectively reduced to an amine, allowing for further functionalization into more sophisticated pharmacophores.

The synthesis of 3,6-Dimethoxy-2-nitropyridine typically involves multi-step organic reactions starting from readily available pyridine derivatives. The introduction of methoxy groups can be achieved through nucleophilic aromatic substitution or metal-catalyzed cross-coupling reactions. Subsequent nitration at the 2-position is commonly performed using classical nitrating agents such as nitric acid in the presence of sulfuric acid. These synthetic routes highlight the compound's accessibility and its suitability for large-scale production.

Recent advances in computational chemistry have further enhanced the utility of 3,6-Dimethoxy-2-nitropyridine in drug design. Molecular modeling studies have revealed that this compound can interact with biological targets through hydrogen bonding networks formed by its nitrogen atoms and oxygen-containing substituents. These interactions are critical for determining binding affinity and selectivity in drug candidates. Additionally, virtual screening techniques have been employed to identify novel analogs of 3,6-Dimethoxy-2-nitropyridine with enhanced pharmacological properties.

The pharmacological profile of 3,6-Dimethoxy-2-nitropyridine has been investigated in various cellular and animal models. Studies have demonstrated its potential as an anti-inflammatory agent by inhibiting pro-inflammatory cytokine production. Furthermore, its ability to modulate neurotransmitter receptors has sparked interest in its role as a potential treatment for neurodegenerative diseases such as Alzheimer's and Parkinson's. These findings underscore the therapeutic relevance of this compound and highlight opportunities for further exploration.

In conclusion,3,6-Dimethoxy-2-nitropyridine (CAS No. 1806291-13-3) represents a significant asset in the pharmaceutical industry due to its versatile structural features and biological activities. Its role as an intermediate in drug synthesis underscores its importance in medicinal chemistry research. As our understanding of disease mechanisms continues to evolve,3,6-Dimethoxy-2-nitropyridine will likely remain at the forefront of efforts to develop innovative therapeutic strategies that address unmet medical needs.

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