Cas no 53653-22-8 (2-hydroxy-6-nitronaphthalene-1-carbaldehyde)

2-Hydroxy-6-nitronaphthalene-1-carbaldehyde is a nitronaphthalene derivative characterized by its aldehyde and hydroxyl functional groups at the 1- and 2-positions, respectively, along with a nitro group at the 6-position. This compound serves as a versatile intermediate in organic synthesis, particularly in the preparation of dyes, pharmaceuticals, and fine chemicals. Its structural features enable selective reactivity in condensation and substitution reactions, making it valuable for constructing complex aromatic systems. The presence of both electron-withdrawing (nitro) and electron-donating (hydroxyl) groups influences its electronic properties, facilitating applications in coordination chemistry and material science. High purity grades are available for research and industrial use, ensuring consistent performance in synthetic workflows.
2-hydroxy-6-nitronaphthalene-1-carbaldehyde structure
53653-22-8 structure
Product Name:2-hydroxy-6-nitronaphthalene-1-carbaldehyde
CAS No:53653-22-8
MF:C11H7NO4
MW:217.177582979202
CID:2759929
PubChem ID:3567973
Update Time:2025-05-24

2-hydroxy-6-nitronaphthalene-1-carbaldehyde Chemical and Physical Properties

Names and Identifiers

    • 2-hydroxy-6-nitronaphthalene-1-carbaldehyde
    • 6-NITRO-2-HYDROXYNAPHTHALENE-1-CARBOXALDEHYDE
    • 2-Hydroxy-6-nitro-[1]naphthaldehyd
    • 2-hydroxy-6-nitro-[1]naphthaldehyde
    • 2-hydroxy-6-nitronaphthaldehyde
    • 2-hydroxy-6-nitro-naphthalene-1-carbaldehyde
    • 6-Nitro-2-hydroxy-naphthaldehyd-(1)
    • NSMXSOJJDHNPSX-UHFFFAOYSA
    • 2-hydroxy-6-nitro-1-naphthaldehyde
    • BBL019081
    • DTXSID30393730
    • NSMXSOJJDHNPSX-UHFFFAOYSA-
    • AKOS005138254
    • SCHEMBL11596295
    • 53653-22-8
    • NSMXSOJJDHNPSX-UHFFFAOYSA-N
    • InChI=1/C11H7NO4/c13-6-10-9-3-2-8(12(15)16)5-7(9)1-4-11(10)14/h1-6,14H
    • DB-082575
    • VS-06875
    • STL197948
    • CS-0327044
    • Inchi: 1S/C11H7NO4/c13-6-10-9-3-2-8(12(15)16)5-7(9)1-4-11(10)14/h1-6,14H
    • InChI Key: NSMXSOJJDHNPSX-UHFFFAOYSA-N
    • SMILES: OC1=CC=C2C=C(C=CC2=C1C=O)[N+](=O)[O-]

Computed Properties

  • Exact Mass: 217.03800
  • Monoisotopic Mass: 217.03750770Da
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 1
  • Complexity: 288
  • 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: 2.7
  • Topological Polar Surface Area: 83.1?2

Experimental Properties

  • PSA: 83.12000
  • LogP: 2.78930

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Additional information on 2-hydroxy-6-nitronaphthalene-1-carbaldehyde

Introduction to 2-hydroxy-6-nitronaphthalene-1-carbaldehyde (CAS No. 53653-22-8)

2-hydroxy-6-nitronaphthalene-1-carbaldehyde, identified by the Chemical Abstracts Service registry number 53653-22-8, is a versatile organic compound that has garnered significant attention in the field of chemical biology and pharmaceutical research. This compound, featuring a naphthalene core substituted with a hydroxyl group at the 2-position and a nitro group at the 6-position, along with an aldehyde functionality at the 1-position, exhibits unique structural and chemical properties that make it a valuable intermediate in synthetic chemistry and drug development.

The naphthalene scaffold is a common motif in many natural products and pharmaceuticals, known for its stability and ability to engage in various biological interactions. The presence of both a hydroxyl group and a nitro group on the naphthalene ring introduces polarity and reactivity, making this compound a promising candidate for further functionalization. The aldehyde group at the 1-position provides a reactive site for condensation reactions, such as Schiff base formation, which is widely used in the synthesis of heterocyclic compounds and metal chelates.

In recent years, 2-hydroxy-6-nitronaphthalene-1-carbaldehyde has been explored in several cutting-edge research areas. One notable application is in the synthesis of bioactive molecules targeting neurological disorders. The nitro group can be reduced to an amine, allowing for the introduction of amine-based pharmacophores that interact with neurotransmitter receptors. This transformation has been investigated in the development of potential treatments for conditions such as Alzheimer's disease and Parkinson's disease, where modulating neurotransmitter activity is key.

Additionally, the hydroxyl and aldehyde functional groups on this compound make it an attractive precursor for constructing more complex molecular architectures. Researchers have utilized 2-hydroxy-6-nitronaphthalene-1-carbaldehyde as a building block in the synthesis of macrocycles and polycycles through cyclization reactions. These larger structures often exhibit enhanced binding affinity to biological targets, making them promising candidates for drug discovery. For instance, derivatives of this compound have been studied for their potential as inhibitors of enzymes involved in cancer metabolism.

The pharmaceutical industry has also shown interest in 2-hydroxy-6-nitronaphthalene-1-carbaldehyde due to its ability to serve as a chiral intermediate. By controlling stereochemistry during synthesis, researchers can produce enantiomerically pure compounds that exhibit improved pharmacological profiles. This approach is particularly relevant in developing drugs that require precise stereochemical control to achieve optimal efficacy while minimizing side effects.

From a synthetic chemistry perspective, 2-hydroxy-6-nitronaphthalene-1-carbaldehyde offers a rich platform for exploring novel reaction pathways. The combination of electron-withdrawing nitro and electron-donating hydroxyl groups facilitates various transformations, including oxidation-reduction cycles, metal-catalyzed coupling reactions, and electrochemical methods. These synthetic strategies are essential for producing derivatives with tailored properties for specific applications.

In academic research, this compound has been employed in studying molecular interactions at the nanoscale. Its rigid aromatic structure allows it to serve as a scaffold for designing probes that can be used in fluorescence microscopy and other imaging techniques. By incorporating fluorophores or affinity tags, researchers can visualize biological processes with high precision, contributing to advancements in fields such as cell biology and immunology.

The environmental impact of using 2-hydroxy-6-nitronaphthalene-1-carbaldehyde has also been considered in recent studies. Efforts have been made to develop greener synthetic routes that minimize waste and reduce energy consumption. These sustainable approaches align with global initiatives to promote environmentally responsible chemical manufacturing practices.

Looking ahead, the future applications of 2-hydroxy-6-nitronaphthalene-1-carbaldehyde are likely to expand as new methodologies emerge in synthetic chemistry and drug discovery. Its unique structural features provide a foundation for innovation across multiple disciplines, from materials science to medicinal chemistry. As research continues to uncover its potential, this compound is poised to play an increasingly important role in advancing scientific knowledge and developing novel therapeutics.

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