Cas no 17953-58-1 (1-Naphthalenecarboxylic acid, 2,7-dimethoxy-)

1-Naphthalenecarboxylic acid, 2,7-dimethoxy-, is a substituted naphthalene derivative featuring methoxy groups at the 2 and 7 positions, along with a carboxylic acid functional group. This compound is of interest in organic synthesis and pharmaceutical research due to its structural versatility, enabling use as a building block for more complex molecules. The electron-donating methoxy groups enhance its reactivity in electrophilic aromatic substitution and metal-catalyzed coupling reactions. Its carboxylic acid moiety allows for further derivatization, such as esterification or amidation. The compound's well-defined aromatic framework and functional group compatibility make it valuable for applications in material science and medicinal chemistry.
1-Naphthalenecarboxylic acid, 2,7-dimethoxy- structure
17953-58-1 structure
Product Name:1-Naphthalenecarboxylic acid, 2,7-dimethoxy-
CAS No:17953-58-1
MF:C13H12O4
MW:232.231984138489
CID:1375559
PubChem ID:12239917
Update Time:2025-06-09

1-Naphthalenecarboxylic acid, 2,7-dimethoxy- Chemical and Physical Properties

Names and Identifiers

    • 1-Naphthalenecarboxylic acid, 2,7-dimethoxy-
    • 2,7-dimethoxynaphthalene-1-carboxylic acid
    • BBL034458
    • SCHEMBL11718070
    • 17953-58-1
    • QQYIGPUPTNLBDQ-UHFFFAOYSA-N
    • VS-12540
    • STL417826
    • 2,7-Dimethoxy-1-naphthoicacid
    • AKOS022658103
    • 2,7-Dimethoxy-1-naphthoic acid
    • DTXSID50481941
    • Inchi: 1S/C13H12O4/c1-16-9-5-3-8-4-6-11(17-2)12(13(14)15)10(8)7-9/h3-7H,1-2H3,(H,14,15)
    • InChI Key: QQYIGPUPTNLBDQ-UHFFFAOYSA-N
    • SMILES: O(C)C1=CC=C2C=CC(=CC2=C1C(=O)O)OC

Computed Properties

  • Exact Mass: 232.07356
  • Monoisotopic Mass: 232.07355886g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 3
  • Complexity: 279
  • 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: 55.8?2

Experimental Properties

  • PSA: 55.76

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Additional information on 1-Naphthalenecarboxylic acid, 2,7-dimethoxy-

Introduction to 1-Naphthalenecarboxylic acid, 2,7-dimethoxy- (CAS No. 17953-58-1)

1-Naphthalenecarboxylic acid, 2,7-dimethoxy-, identified by its Chemical Abstracts Service (CAS) number 17953-58-1, is a specialized organic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal biology. This compound, belonging to the class of naphthalene derivatives, features two methoxy groups at the 2 and 7 positions of the naphthalene core, which confer unique electronic and steric properties. These structural characteristics make it a valuable intermediate in the synthesis of various biologically active molecules.

The 2,7-dimethoxy substitution pattern on the naphthalene ring enhances the compound's solubility in polar solvents while maintaining its aromatic stability. This balance is crucial for its application in drug design, where solubility and metabolic stability are key factors influencing bioavailability and efficacy. Recent advancements in computational chemistry have allowed researchers to predict the binding affinity of this compound to various biological targets with high precision, paving the way for its potential use in targeted therapy.

In recent years, 1-Naphthalenecarboxylic acid, 2,7-dimethoxy- has been explored as a precursor in the synthesis of novel therapeutic agents. Its structural framework is reminiscent of many natural products and pharmacophores that exhibit significant biological activity. For instance, derivatives of this compound have shown promise in inhibiting enzymes involved in inflammatory pathways. Studies have demonstrated that modifications at the 2 and 7 methoxy positions can fine-tune the pharmacological properties of the resulting molecules, leading to compounds with enhanced selectivity and reduced side effects.

The pharmaceutical industry has been particularly interested in leveraging this compound for its potential in developing treatments for neurological disorders. The naphthalene core is known to interact with certain neurotransmitter receptors, making it a viable scaffold for neuroactive compounds. Researchers have synthesized analogs of 1-Naphthalenecarboxylic acid, 2,7-dimethoxy- that exhibit properties similar to known neuroprotective agents. Preliminary studies suggest that these derivatives may offer a new approach to managing conditions such as Alzheimer's disease and Parkinson's disease by modulating neuronal signaling pathways.

Moreover, the dimethoxy substitution on the naphthalene ring influences the electronic distribution across the molecule, which can be exploited to enhance photophysical properties. This has opened up possibilities for applications in photodynamic therapy and imaging techniques. By incorporating this compound into photosensitizer molecules, scientists aim to develop more efficient systems for treating cancer and other degenerative diseases. The ability to tune both steric and electronic effects through strategic functionalization makes 1-Naphthalenecarboxylic acid, 2,7-dimethoxy- a versatile building block for innovative drug discovery.

From a synthetic chemistry perspective, 1-Naphthalenecarboxylic acid, 2,7-dimethoxy- serves as a critical intermediate in multi-step syntheses. The presence of carboxylic acid functionality at one end of the naphthalene ring allows for further derivatization via esterification or amidation reactions. This flexibility enables chemists to construct complex molecular architectures with tailored biological activities. Recent reports highlight its use in generating libraries of heterocyclic compounds that are screened for their antimicrobial and anti-inflammatory properties.

The biotechnological relevance of this compound extends beyond traditional drug development. Its structural motif is also found in natural products used by medicinal plants as defense mechanisms against pathogens. By studying how plants biosynthesize related compounds, researchers can gain insights into potential therapeutic applications for derivatives of 1-Naphthalenecarboxylic acid, 2,7-dimethoxy-. This interdisciplinary approach combines organic chemistry with ethnobotany and pharmacognosy to uncover novel bioactive molecules.

In conclusion,1-Naphthalenecarboxylic acid, 2,7-dimethoxy- (CAS No. 17953-58-1) represents a fascinating subject of study due to its structural versatility and biological potential. The strategic placement of methoxy groups on the naphthalene core imparts unique chemical properties that make it indispensable in synthetic pharmaceuticals and biotechnology. As research continues to uncover new applications for this compound, its importance is likely to grow further within both academic and industrial settings.

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