Cas no 50493-10-2 (1-methoxynaphthalene-2-carbaldehyde)

1-Methoxynaphthalene-2-carbaldehyde is a versatile aromatic aldehyde featuring a methoxy-substituted naphthalene core. Its distinct structure combines the reactivity of an aldehyde group with the stability and electron-rich nature of the methoxynaphthalene moiety, making it a valuable intermediate in organic synthesis. This compound is particularly useful in the preparation of pharmaceuticals, agrochemicals, and functional materials due to its ability to undergo condensation, oxidation, and nucleophilic addition reactions. The methoxy group enhances solubility in organic solvents and influences electronic properties, facilitating selective functionalization. Its high purity and well-defined reactivity profile make it a reliable choice for research and industrial applications requiring precise molecular modifications.
1-methoxynaphthalene-2-carbaldehyde structure
50493-10-2 structure
Product Name:1-methoxynaphthalene-2-carbaldehyde
CAS No:50493-10-2
MF:C12H10O2
MW:186.206603527069
MDL:MFCD17012300
CID:364809
PubChem ID:13119993
Update Time:2025-06-09

1-methoxynaphthalene-2-carbaldehyde Chemical and Physical Properties

Names and Identifiers

    • 2-Naphthalenecarboxaldehyde, 1-methoxy-
    • 1-Methoxy-naphthalene-2-carbaldehyde
    • 1-methoxynaphthalene-2-carbaldehyde
    • 1-Methoxynaphthalene-2-carboxaldehyde
    • VPMICVLTBHRPNL-UHFFFAOYSA-N
    • CS-0061935
    • DTXSID00519460
    • SY205384
    • Z1255363268
    • MFCD17012300
    • 50493-10-2
    • SCHEMBL3563735
    • 1-methoxy-2-naphthalenecarboxaldehyde
    • AS-63320
    • EN300-226206
    • AKOS022505508
    • FT-0716933
    • 1-methoxy-2-naphthaldehyde
    • DB-083703
    • MDL: MFCD17012300
    • Inchi: 1S/C12H10O2/c1-14-12-10(8-13)7-6-9-4-2-3-5-11(9)12/h2-8H,1H3
    • InChI Key: VPMICVLTBHRPNL-UHFFFAOYSA-N
    • SMILES: O(C)C1C(C=O)=CC=C2C=CC=CC2=1

Computed Properties

  • Exact Mass: 186.0681
  • Monoisotopic Mass: 186.068079557g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 2
  • Complexity: 203
  • 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: 2.6
  • Topological Polar Surface Area: 26.3?2

Experimental Properties

  • PSA: 26.3

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Additional information on 1-methoxynaphthalene-2-carbaldehyde

Introduction to 1-methoxynaphthalene-2-carbaldehyde (CAS No. 50493-10-2)

1-methoxynaphthalene-2-carbaldehyde, identified by its Chemical Abstracts Service (CAS) number 50493-10-2, is a significant compound in the realm of organic chemistry and pharmaceutical research. This aromatic aldehyde, characterized by a methoxy group at the 1-position and a formyl group at the 2-position of a naphthalene core, has garnered considerable attention due to its versatile applications in synthetic chemistry and as a key intermediate in the development of biologically active molecules.

The structural motif of 1-methoxynaphthalene-2-carbaldehyde makes it a valuable building block for constructing more complex chemical entities. The presence of both electron-donating (methoxy) and electron-withdrawing (formyl) groups on the naphthalene ring system imparts unique reactivity, enabling diverse functionalization strategies. This compound serves as a crucial precursor in the synthesis of heterocyclic compounds, which are widely prevalent in medicinal chemistry.

In recent years, 1-methoxynaphthalene-2-carbaldehyde has been extensively explored in the development of novel pharmaceutical agents. Its aldehyde functionality allows for condensation reactions with various nucleophiles, facilitating the formation of Schiff bases, imines, and other nitrogen-containing heterocycles. These derivatives have demonstrated promising biological activities, including antimicrobial, anti-inflammatory, and anticancer properties. The methoxy group further enhances its utility by enabling selective modifications while preserving the inherent reactivity of the aldehyde.

One of the most compelling aspects of 1-methoxynaphthalene-2-carbaldehyde is its role in the synthesis of small-molecule inhibitors targeting enzyme-catalyzed reactions. Enzymes such as kinases and proteases are critical mediators of cellular signaling pathways and are often implicated in diseases like cancer and inflammatory disorders. By designing molecules that mimic or inhibit these enzymes, researchers can develop therapeutic strategies to modulate cellular processes. The aldehyde group in 1-methoxynaphthalene-2-carbaldehyde provides a handle for covalent bond formation with catalytic residues in enzymes, leading to the development of potent inhibitors.

Advances in computational chemistry have further enhanced the utility of 1-methoxynaphthalene-2-carbaldehyde as a scaffold for drug discovery. Molecular modeling techniques allow researchers to predict how this compound interacts with biological targets at an atomic level. By integrating experimental data with computational predictions, scientists can optimize the structure of 1-methoxynaphthalene-2-carbaldehyde derivatives to improve their binding affinity and selectivity. This approach has led to the identification of novel lead compounds with improved pharmacokinetic profiles.

The synthesis of 1-methoxynaphthalene-2-carbaldehyde itself is an area of active research. Traditional methods involve oxidation of 1-methoxynaphthalene, but recent studies have explored more efficient and sustainable routes. For instance, catalytic oxidation using environmentally benign oxidants has been reported to provide high yields with minimal byproducts. Such green chemistry approaches align with the growing emphasis on sustainable practices in pharmaceutical manufacturing.

Another exciting application of 1-methoxynaphthalene-2-carbaldehyde lies in its use as a chiral building block. Chiral molecules are non-superimposable mirror images, and their enantiomers can exhibit drastically different biological activities. By incorporating chiral auxiliaries or catalysts during synthesis, researchers can generate enantiomerically enriched derivatives of 1-methoxynaphthalene-2-carbaldehyde, which may exhibit enhanced therapeutic efficacy with reduced side effects.

The role of 1-methoxynaphthalene-2-carbaldehyde in material science is also noteworthy. Its aromatic structure and functional groups make it a suitable candidate for designing organic semiconductors and luminescent materials. These materials are integral to technologies such as organic light-emitting diodes (OLEDs) and photovoltaic cells. By tuning the electronic properties through functionalization, researchers can develop materials with tailored optoelectronic characteristics for various applications.

In conclusion, 1-methoxynaphthalene-2-carbaldehyde (CAS No. 50493-10-2) is a multifaceted compound with broad applications across synthetic chemistry, pharmaceutical research, and material science. Its unique structural features enable diverse chemical transformations, making it an indispensable tool for developing novel biologically active molecules and advanced materials. As research continues to uncover new methodologies and applications, the significance of this compound is expected to grow even further.

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