Cas no 80200-09-5 (1-(4-hydroxybenzyl)pyrazole)

1-(4-Hydroxybenzyl)pyrazole is a pyrazole derivative featuring a hydroxyphenyl substituent, offering versatile reactivity for synthetic applications. Its structure combines the aromatic properties of the phenol moiety with the heterocyclic functionality of pyrazole, making it a valuable intermediate in medicinal chemistry and material science. The hydroxyl group enhances solubility in polar solvents and provides a site for further functionalization, such as etherification or esterification. This compound is particularly useful in the development of pharmacologically active molecules, owing to its potential as a scaffold for bioactive agents. Its stability and well-defined reactivity profile ensure consistent performance in organic synthesis and ligand design.
1-(4-hydroxybenzyl)pyrazole structure
1-(4-hydroxybenzyl)pyrazole structure
Product Name:1-(4-hydroxybenzyl)pyrazole
CAS No:80200-09-5
MF:C10H10N2O
MW:174.199202060699
CID:985245
PubChem ID:133412
Update Time:2025-06-13

1-(4-hydroxybenzyl)pyrazole Chemical and Physical Properties

Names and Identifiers

    • 1-(4-hydroxybenzyl)pyrazole
    • phenol, 4-(1H-pyrazol-1-ylmethyl)-
    • 4-(1H-pyrazol-1-ylmethyl)Phenol
    • 4-(pyrazol-1-ylmethyl)phenol
    • AKOS018656003
    • 4-[(1H-pyrazol-1-yl)methyl]phenol
    • CS-0374539
    • SLCYYEKQDZIXOZ-UHFFFAOYSA-N
    • FT-0702986
    • DTXSID30230151
    • 4-((1H-pyrazol-1-yl)methyl)phenol
    • SCHEMBL7627846
    • 4-Hobp
    • EN300-3176684
    • 80200-09-5
    • 4-(1-pyrazolyl)methylphenol
    • DA-22985
    • Inchi: 1S/C10H10N2O/c13-10-4-2-9(3-5-10)8-12-7-1-6-11-12/h1-7,13H,8H2
    • InChI Key: SLCYYEKQDZIXOZ-UHFFFAOYSA-N
    • SMILES: OC1C=CC(=CC=1)CN1C=CC=N1

Computed Properties

  • Exact Mass: 174.079
  • Monoisotopic Mass: 174.079
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 2
  • Complexity: 155
  • 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
  • Surface Charge: 0
  • Tautomer Count: 2
  • XLogP3: nothing
  • Topological Polar Surface Area: 38?2

Experimental Properties

  • Density: 1.16
  • Boiling Point: 364.8°C at 760 mmHg
  • Flash Point: 174.4°C
  • Refractive Index: 1.604

1-(4-hydroxybenzyl)pyrazole Pricemore >>

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Additional information on 1-(4-hydroxybenzyl)pyrazole

Introduction to 1-(4-hydroxybenzyl)pyrazole (CAS No. 80200-09-5)

1-(4-hydroxybenzyl)pyrazole, identified by its Chemical Abstracts Service (CAS) number 80200-09-5, is a heterocyclic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal research. This compound belongs to the pyrazole class, a scaffold that is widely recognized for its diverse biological activities and potential therapeutic applications. The presence of a 4-hydroxybenzyl substituent in its molecular structure introduces unique pharmacophoric features, making it a valuable intermediate in the synthesis of various bioactive molecules.

The pyrazole core is a five-membered aromatic ring containing two nitrogen atoms, which contributes to its stability and reactivity. The 4-hydroxybenzyl group, on the other hand, provides hydrophilic properties and potential sites for further functionalization. This combination of structural elements has positioned 1-(4-hydroxybenzyl)pyrazole as a compound of interest in the development of novel drugs targeting a range of diseases.

In recent years, there has been a surge in research focused on identifying and developing new therapeutic agents derived from pyrazole derivatives. The structural flexibility of pyrazole allows for the introduction of various substituents, enabling the tuning of biological activity to meet specific pharmacological requirements. Among these derivatives, 1-(4-hydroxybenzyl)pyrazole has shown promise in several preclinical studies.

One of the most compelling areas of research involving 1-(4-hydroxybenzyl)pyrazole is its potential as an anti-inflammatory agent. Inflammation is a hallmark of numerous chronic diseases, and inhibiting inflammatory pathways has been a major focus in drug discovery. Studies have demonstrated that pyrazole derivatives can modulate inflammatory responses by interacting with key signaling molecules such as cyclooxygenase (COX) and lipoxygenase (LOX). The 4-hydroxybenzyl moiety in 1-(4-hydroxybenzyl)pyrazole may enhance its ability to interact with these enzymes, potentially leading to more effective anti-inflammatory effects.

Furthermore, the compound has been investigated for its antimicrobial properties. Antibiotic resistance is a growing global health concern, and there is an urgent need for new antimicrobial agents. Preliminary studies suggest that 1-(4-hydroxybenzyl)pyrazole can exhibit activity against certain bacterial strains by disrupting essential cellular processes. The hydroxyl group in the 4-hydroxybenzyl substituent may play a crucial role in this mechanism by facilitating interactions with bacterial cell membranes or enzymes.

The pharmacokinetic profile of 1-(4-hydroxybenzyl)pyrazole is also an area of active investigation. Understanding how a compound is absorbed, distributed, metabolized, and excreted (ADME) is critical for determining its clinical efficacy and safety. Research indicates that the presence of the hydroxyl group may influence the compound's solubility and metabolic pathways, which could impact its bioavailability and duration of action.

Recent advances in computational chemistry have further enhanced the study of 1-(4-hydroxybenzyl)pyrazole. Molecular modeling techniques allow researchers to predict how this compound might interact with biological targets at the atomic level. These simulations have been instrumental in guiding synthetic modifications aimed at optimizing its pharmacological properties. For instance, virtual screening has identified structural analogs of 1-(4-hydroxybenzyl)pyrazole that may exhibit enhanced potency or selectivity.

In addition to its pharmaceutical applications, 1-(4-hydroxybenzyl)pyrazole has shown potential in material science. Pyrazole derivatives are known for their ability to form coordination complexes with metal ions, making them useful in catalysis and material design. The unique electronic properties of the 4-hydroxybenzyl group may further enhance these interactions, opening up new possibilities for applications such as sensors or luminescent materials.

The synthesis of 1-(4-hydroxybenzyl)pyrazole involves multi-step organic reactions that require careful optimization to ensure high yield and purity. Common synthetic routes include condensation reactions between hydrazine derivatives and β-ketoesters or ketones, followed by functional group transformations to introduce the 4-hydroxybenzyl moiety. Advances in green chemistry have also led to the development of more sustainable synthetic methods, reducing waste and energy consumption.

Evaluation of 1-(4-hydroxybenzyl)pyrazole in preclinical models has provided valuable insights into its potential therapeutic applications. Animal studies have shown that it can modulate immune responses and reduce inflammation without significant side effects at effective doses. These findings have paved the way for clinical trials involving patients with inflammatory disorders such as rheumatoid arthritis or inflammatory bowel disease.

The development of novel drug candidates like 1-(4-hydroxybenzyl)pyrazole relies heavily on collaboration between academic researchers and pharmaceutical companies. Open innovation models have accelerated this process by fostering partnerships that combine expertise from different disciplines. Such collaborations have been crucial in translating laboratory discoveries into viable therapeutic options for patients worldwide.

Looking ahead, continued research on 1-(4-hydroxybenzyl)pyrazole holds promise for uncovering new therapeutic uses and refining its pharmacological properties. Emerging technologies such as CRISPR gene editing and artificial intelligence-driven drug discovery are expected to further enhance our understanding of this compound's potential applications.

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