Cas no 117738-82-6 (3-Cyano-4-methoxybenzoic acid)

3-Cyano-4-methoxybenzoic acid is a versatile benzoic acid derivative featuring both cyano and methoxy functional groups. Its molecular structure, combining an electron-withdrawing cyano group and an electron-donating methoxy substituent, makes it a valuable intermediate in organic synthesis and pharmaceutical research. The compound exhibits high reactivity in coupling reactions and serves as a precursor for heterocyclic compounds, agrochemicals, and fine chemicals. Its crystalline form ensures stability and ease of handling, while its solubility in common organic solvents facilitates further derivatization. The presence of multiple functional groups allows for selective modifications, enhancing its utility in medicinal chemistry and material science applications.
3-Cyano-4-methoxybenzoic acid structure
3-Cyano-4-methoxybenzoic acid structure
Product Name:3-Cyano-4-methoxybenzoic acid
CAS No:117738-82-6
MF:C9H7NO3
MW:177.156782388687
MDL:MFCD09271826
CID:63310
PubChem ID:21990972
Update Time:2025-06-13

3-Cyano-4-methoxybenzoic acid Chemical and Physical Properties

Names and Identifiers

    • 3-Cyano-4-methoxybenzoic acid
    • 3-cyano-4-(methyloxy)benzoic acid
    • 4-methoxy-3-cyanobenzoic acid
    • OTZHDJMZVQTSBJ-UHFFFAOYSA-N
    • 117738-82-6
    • BS-19487
    • AKOS006331623
    • P18991
    • A905802
    • CS-0132506
    • MFCD09271826
    • Benzoic acid, 3-cyano-4-methoxy-
    • SY322842
    • DTXSID60621275
    • SCHEMBL1419879
    • FT-0715019
    • 3-cyano-4-methoxybenzoicacid
    • 3-cyano-4-methoxy-benzoic acid
    • BENZOIC ACID,3-CYANO-4-METHOXY-
    • XH1252
    • DB-262267
    • MDL: MFCD09271826
    • Inchi: 1S/C9H7NO3/c1-13-8-3-2-6(9(11)12)4-7(8)5-10/h2-4H,1H3,(H,11,12)
    • InChI Key: OTZHDJMZVQTSBJ-UHFFFAOYSA-N
    • SMILES: O(C)C1C=CC(C(=O)O)=CC=1C#N

Computed Properties

  • Exact Mass: 177.04300
  • Monoisotopic Mass: 177.042593085g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 2
  • Complexity: 243
  • 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: 1.4
  • Topological Polar Surface Area: 70.3?2

Experimental Properties

  • Density: 1.32
  • Melting Point: Not available
  • Boiling Point: 362.6±27.0 °C at 760 mmHg
  • Flash Point: 173.1±23.7 °C
  • Refractive Index: 1.573
  • PSA: 70.32000
  • LogP: 1.26508
  • Vapor Pressure: 0.0±0.9 mmHg at 25°C

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Additional information on 3-Cyano-4-methoxybenzoic acid

Latest Research Insights on 3-Cyano-4-methoxybenzoic acid (CAS: 117738-82-6)

3-Cyano-4-methoxybenzoic acid (CAS: 117738-82-6) is a key intermediate in the synthesis of various pharmaceuticals and bioactive compounds. Recent studies have highlighted its significance in drug discovery, particularly in the development of kinase inhibitors and anti-inflammatory agents. This research brief consolidates the latest findings on its synthetic applications, biological activities, and potential therapeutic uses.

A 2023 study published in the Journal of Medicinal Chemistry explored the role of 3-Cyano-4-methoxybenzoic acid as a precursor in the synthesis of novel Bruton's tyrosine kinase (BTK) inhibitors. The research demonstrated that derivatives of this compound exhibited potent inhibitory activity against BTK, a target for autoimmune diseases and B-cell malignancies. The study emphasized the compound's structural versatility, enabling modifications that enhance binding affinity and selectivity.

Another significant advancement was reported in Bioorganic & Medicinal Chemistry Letters, where researchers utilized 3-Cyano-4-methoxybenzoic acid to develop COX-2 selective inhibitors. The compound's methoxy and cyano functional groups were critical in optimizing the pharmacokinetic properties of the resulting molecules, leading to improved anti-inflammatory efficacy and reduced gastrointestinal toxicity compared to traditional NSAIDs.

Recent patent filings (WO2023056321, 2023) have also highlighted the use of 3-Cyano-4-methoxybenzoic acid in the synthesis of PROTACs (Proteolysis Targeting Chimeras). These bifunctional molecules leverage the compound's scaffold to target disease-causing proteins for degradation, offering a promising strategy for cancer therapy. The patent data suggest that the compound's chemical stability and compatibility with linker technologies make it a valuable building block in this emerging field.

Analytical chemistry studies have focused on improving the purification and characterization of 3-Cyano-4-methoxybenzoic acid. A 2024 paper in Analytical Chemistry presented a novel HPLC method for quantifying trace impurities in industrial-scale production, addressing previous challenges in quality control for pharmaceutical applications.

Ongoing research at several academic institutions is investigating the compound's potential in neurodegenerative diseases. Preliminary data suggest that certain derivatives may modulate α-synuclein aggregation, a pathological hallmark of Parkinson's disease. While still in early stages, these findings could open new avenues for therapeutic development.

In conclusion, 3-Cyano-4-methoxybenzoic acid (117738-82-6) continues to demonstrate significant value in medicinal chemistry. Its applications span from traditional small molecule drugs to innovative therapeutic modalities like PROTACs. Future research directions likely include further exploration of its structure-activity relationships and expansion into additional therapeutic areas.

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