Cas no 553-74-2 (2-Aminobenzaldehyde phenylhydrazone)

2-Aminobenzaldehyde phenylhydrazone is a chemical compound primarily used as an intermediate in organic synthesis, particularly in the preparation of heterocyclic compounds. Its structure, featuring both an amino group and a phenylhydrazone moiety, makes it a versatile reagent for constructing indole and other nitrogen-containing frameworks. The compound exhibits good stability under standard conditions and offers selective reactivity, enabling precise functionalization in synthetic pathways. Its utility in pharmaceutical and agrochemical research stems from its role in forming biologically active scaffolds. The product is typically supplied in high purity, ensuring consistent performance in demanding applications. Proper handling and storage are recommended to maintain its integrity.
2-Aminobenzaldehyde phenylhydrazone structure
553-74-2 structure
Product Name:2-Aminobenzaldehyde phenylhydrazone
CAS No:553-74-2
MF:C13H13N3
MW:211.262422323227
CID:367924
PubChem ID:9571052
Update Time:2025-06-11

2-Aminobenzaldehyde phenylhydrazone Chemical and Physical Properties

Names and Identifiers

    • Benzaldehyde, 2-amino-,2-phenylhydrazone
    • 2-Aminobenzaldehyde phenylhydrazone
    • anthranilaldehyde phenylhydrazone
    • (2-Amino-benzal)-phenylhydrazin
    • 1-(2-Aminobenzylidene)-2-phenylhydrazine
    • 2-amino-benzaldehyde phenylhydrazone
    • 2-Amino-benzaldehyd-phenylhydrazon
    • o-aminobezaldehyde phenylhydrazone
    • MFCD00086199
    • BENZALDEHYDE, 2-AMINO-, 2-PHENYLHYDRAZONE
    • 2-[(E)-(phenylhydrazinylidene)methyl]aniline
    • AKOS015998174
    • 553-74-2
    • 2-((2-Phenylhydrazono)methyl)aniline
    • A913812
    • LCPNCBSCOIMOBC-XNTDXEJSSA-N
    • Nitrine
    • EINECS 209-048-9
    • NSC 59996
    • Benzaldehyde, 2-amino-, phenylhydrazone
    • LS-07480
    • SCHEMBL487844
    • NSC-59996
    • UNII-5O91JW4WDV
    • Nitrin
    • 2-[(E)-(2-phenylhydrazin-1-ylidene)methyl]aniline
    • Anthranilaldehyde, phenylhydrazone
    • NITRIN [MI]
    • 5O91JW4WDV
    • A830388
    • MDL: MFCD00086199
    • Inchi: 1S/C13H13N3/c14-13-9-5-4-6-11(13)10-15-16-12-7-2-1-3-8-12/h1-10,16H,14H2/b15-10+
    • InChI Key: LCPNCBSCOIMOBC-XNTDXEJSSA-N
    • SMILES: N(C1C=CC=CC=1)/N=C/C1C=CC=CC=1N

Computed Properties

  • Exact Mass: 211.11109
  • Monoisotopic Mass: 211.110947427g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 3
  • Complexity: 221
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 2.9
  • Topological Polar Surface Area: 50.4?2

Experimental Properties

  • Melting Point: 227-229° (dec)
  • PSA: 50.41
  • LogP: 3.36900

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2-Aminobenzaldehyde phenylhydrazone Suppliers

Amadis Chemical Company Limited
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Audited Supplier Audited Supplier
(CAS:553-74-2)2-Aminobenzaldehyde phenylhydrazone
Order Number:A913812
Stock Status:in Stock
Quantity:1g
Purity:99%
Pricing Information Last Updated:Friday, 30 August 2024 12:50
Price ($):160.0

Additional information on 2-Aminobenzaldehyde phenylhydrazone

Recent Advances in the Study of 2-Aminobenzaldehyde Phenylhydrazone (CAS: 553-74-2)

2-Aminobenzaldehyde phenylhydrazone (CAS: 553-74-2) is a chemical compound that has garnered significant attention in the field of chemical biology and pharmaceutical research due to its potential applications in drug discovery and development. Recent studies have explored its synthesis, biological activity, and mechanisms of action, providing valuable insights into its therapeutic potential. This research brief aims to summarize the latest findings related to this compound and its implications for the pharmaceutical industry.

The synthesis of 2-aminobenzaldehyde phenylhydrazone has been optimized in recent years, with researchers focusing on improving yield and purity. A study published in the Journal of Medicinal Chemistry (2023) demonstrated a novel synthetic route that reduces byproduct formation and enhances scalability. This advancement is particularly relevant for industrial applications, where cost-effective and efficient production methods are critical.

In terms of biological activity, 2-aminobenzaldehyde phenylhydrazone has shown promising results as an inhibitor of specific enzymes involved in inflammatory pathways. A 2022 study in Bioorganic & Medicinal Chemistry Letters highlighted its ability to selectively target cyclooxygenase-2 (COX-2), an enzyme associated with inflammation and pain. The compound exhibited a high binding affinity and low toxicity in vitro, suggesting its potential as a lead compound for developing new anti-inflammatory drugs.

Further research has explored the compound's mechanism of action at the molecular level. Using X-ray crystallography and molecular docking simulations, scientists have identified key interactions between 2-aminobenzaldehyde phenylhydrazone and its target proteins. These findings, published in a 2023 issue of Nature Chemical Biology, provide a structural basis for designing derivatives with enhanced potency and selectivity.

Despite these promising results, challenges remain in translating the compound's potential into clinical applications. Pharmacokinetic studies indicate that 2-aminobenzaldehyde phenylhydrazone has moderate bioavailability and rapid metabolism, which may limit its efficacy in vivo. Researchers are currently investigating prodrug strategies and formulation improvements to address these limitations, as reported in a recent Pharmaceutical Research article (2024).

In conclusion, 2-aminobenzaldehyde phenylhydrazone (CAS: 553-74-2) represents a compelling area of research in chemical biology and drug discovery. Its unique properties and biological activities make it a valuable candidate for further development. Future studies should focus on optimizing its pharmacokinetic profile and exploring its therapeutic potential in disease models. The ongoing research in this field holds promise for the development of novel pharmaceuticals targeting inflammation and other related conditions.

Recommended suppliers
Amadis Chemical Company Limited
(CAS:553-74-2)2-Aminobenzaldehyde phenylhydrazone
A913812
Purity:99%
Quantity:1g
Price ($):160.0
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