Production Method 1

27258-04-4

288-13-1

90499-57-3

930-36-9

80510-03-8

289-95-2

Reaction Conditions

Reference

Flash vacuum pyrolysis of bis- and tris(pyrazol-1-yl)methane. A radical reaction

Perez, Jorge D.; et al, Tetrahedron, 1988, 44(20), 6429-34

Production Method 2

80510-03-8

288-13-1

90499-57-3

930-36-9

80510-03-8

289-95-2

Reaction Conditions

Reference

Flash vacuum pyrolysis of bis- and tris(pyrazol-1-yl)methane. A radical reaction

Perez, Jorge D.; et al, Tetrahedron, 1988, 44(20), 6429-34

1H-pyrazole Raw materials

• 1H-Pyrazole,1,1'-methylenebis-
• Tris(1-pyrazolyl)methane

1H-pyrazole Preparation Products

• 1,1'-Bipyrazole (90499-57-3)
• 1H-pyrazole (288-13-1)
• 1-methyl-1H-pyrazole (930-36-9)
• Tris(1-pyrazolyl)methane (80510-03-8)
• Pyrimidine (289-95-2)

• 1. Synthesis and in vitro antibacterial activity of novel fluoroalkyl-substituted pyrazolyl oxazolidinones
  Lili Yan,Jingjing Wu,Heng Chen,Shaowu Zhang,Zhi Wang,Hui Wang,Fanhong Wu RSC Adv. 2015 5 73660
• 2. Low catalyst loading enabled organocatalytic synthesis of chiral bis-heterocyclic frameworks containing pyrazole and isoxazole
  Banni Preet Kaur,Vivek Sharma,Subash Chandra Sahoo,Swapandeep Singh Chimni Org. Biomol. Chem. 2021 19 9910
• 3. Synthesis, antimicrobial and ergosterol biosynthesis inhibition activity of clubbed 1,1′-biphenyl-pyrazole derivatives
  Yogesh Walunj,Yogesh Nandurkar,Abhijit Shinde,Shivaji Jagadale,Abdul Latif N. Shaikh,Manisha Modak,Pravin C. Mhaske New J. Chem. 2023 47 3810
• 4. Synthesis of N-substituted quaternary carbon centers through KOt-Bu-catalyzed aza-Michael addition of pyrazoles to cyclic enones
  Subin Yoon,Sungbin Lee,Seung Hyun Nam,Hyejeong Lee,Yunmi Lee Org. Biomol. Chem. 2022 20 8313
• 5. Pyrazole–oxadiazole conjugates: synthesis, antiproliferative activity and inhibition of tubulin polymerization
  Ahmed Kamal,Anver Basha Shaik,Sowjanya Polepalli,Vangala Santosh Reddy,G. Bharath Kumar,Soma Gupta,K. V. S. Rama Krishna,Ananthamurthy Nagabhushana,Rakesh K. Mishra,Nishant Jain Org. Biomol. Chem. 2014 12 7993

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Azoles Pyrazoles
• Solvents and Organic Chemicals Organic Compounds Heterocyclic Compounds

Synthesis, Properties, and Cutting-Edge Applications of 1H-Pyrazole (CAS No. 288-13-1)

1H-Pyrazole, identified by the Chemical Abstracts Service (CAS) registry number 288-13-1, is a fundamental heterocyclic compound with the molecular formula C?H?N?. Its structure consists of a five-membered ring comprising two nitrogen atoms and three carbon atoms, forming a conjugated system that imparts unique electronic and chemical properties. This aromatic scaffold serves as a versatile platform for the design of pharmaceuticals, agrochemicals, and advanced materials due to its ability to form stable complexes with transition metals and its reactivity toward functionalization. Recent advancements in synthetic methodologies have further expanded its utility in diverse applications.

The core structure of pyrazole (CAS No. 288-13-1) has been leveraged in drug discovery to enhance bioactivity profiles. For instance, studies published in the Journal of Medicinal Chemistry (2023) highlight its role as a pharmacophore in anti-inflammatory agents, where substitution at the 3 or 4 position introduces potent COX-inhibitory activity without gastrointestinal side effects traditionally associated with nonsteroidal drugs. Computational docking simulations revealed that the nitrogen-containing ring facilitates hydrogen bonding interactions with target enzymes, optimizing molecular recognition.

In oncology research, derivatives of pyrazole have emerged as promising anticancer candidates through mechanisms such as topoisomerase inhibition and disruption of tumor cell metabolism. A 2024 study from Nature Communications demonstrated that pyridopyrazole hybrids exhibit selective cytotoxicity against pancreatic cancer cells by modulating the Akt/mTOR signaling pathway. The rigid planar structure of pyrazole allows efficient π-stacking interactions with DNA molecules, making it an ideal component for developing nucleic acid-targeting therapeutics.

The field of catalysis has seen innovative applications through metal-pyrazolate complexes reported in Angewandte Chemie (2024). These complexes exhibit exceptional stability under harsh reaction conditions due to the strong N-donor ligand properties of pyrazole's nitrogen atoms. In particular, palladium(II)-pyrazolate catalysts have shown unprecedented efficiency in Suzuki-Miyaura cross-coupling reactions at room temperature, reducing energy consumption by over 60% compared to conventional systems. Such advancements underscore the compound's value in sustainable chemical synthesis.

In materials science, researchers at MIT recently synthesized a novel metal-organic framework (Metal Organic Framework) incorporating pyrazolate linkers that exhibits tunable porosity for gas storage applications (Science Advances 2024). The pyrazole units provided enhanced thermal stability up to 450°C while maintaining high surface area (~500 m2/g), outperforming traditional carboxylate-based MOFs under similar conditions. This structural versatility is attributed to the compound's ability to form bidentate chelates with metal ions through its adjacent nitrogen atoms.

Emerging studies in neuroprotection reveal that certain pyrazole derivatives act as potent neurotrophic factors mimetics (ACS Chemical Neuroscience 2024). A benzopyrazole scaffold functionalized with hydroxamic acid groups demonstrated selective binding to amyloid-beta plaques associated with Alzheimer's disease while promoting neuronal growth factor secretion in vitro. The rigid aromatic system facilitates precise molecular recognition required for targeting neurodegenerative pathologies without affecting healthy brain tissue.

In photovoltaic research, Pyrazole-based dyes are being explored as sensitizers for dye-sensitized solar cells (DSSCs). A 2024 paper from Advanced Energy Materials reported that incorporating pyrazole into ruthenium(II) polypyridyl complexes increased light-harvesting efficiency by extending absorption into near-infrared wavelengths while maintaining charge transport properties through π-conjugation pathways inherent to the pyrazole core.

The compound's redox properties have also found application in electrochemical sensors developed at Stanford University (Analytical Chemistry 2024). Pyrazolyl-functionalized graphene electrodes showed remarkable sensitivity toward dopamine detection due to favorable electron transfer kinetics at the interface between the conjugated heterocycle and carbon nanomaterials. This innovation enables real-time monitoring systems for biomedical diagnostics requiring sub-nanomolar detection limits.

Recent advances in green chemistry have optimized synthesis routes for CAS No. 288-13-1. A microwave-assisted method published in Green Chemistry (Q4 2023) achieved over 95% yield using solvent-free conditions and heterogeneous catalysts derived from bio-waste materials such as almond shells carbonized into activated charcoal catalysts (Heterogeneous Catalysts). This approach reduces environmental impact while maintaining high product purity through rapid reaction kinetics under controlled thermal regimes.

Bioisosteric replacements involving pyrazole structures are revolutionizing drug design strategies according to a review article in Drug Discovery Today (January 2024). Replacing phenyl rings with pyrrolopyrazoles preserves pharmacokinetic profiles while enhancing metabolic stability through increased rigidity of the conjugated system (Bioisosteric Replacement Strategy). This substitution was successfully applied in developing next-generation kinase inhibitors where traditional benzene rings led to rapid phase I metabolism issues.

In enzymology studies published this year (Nature Catalysis, March 2024), engineered enzymes capable of selectively oxidizing pyrazoles were identified through directed evolution techniques (Directed Evolution Techniques). These mutant cytochrome P450 variants enable regioselective hydroxylation at position N? under mild aqueous conditions without requiring toxic oxidants like hydrogen peroxide or dichloroisocyanuric acid (e.g., N-chlorosuccinimide). Such biocatalysts are poised to transform industrial processes requiring site-specific modifications on complex heterocycles.

Cryogenic electron microscopy (CryoEM) studies conducted at Harvard Medical School revealed unprecedented insights into protein-pyrazole interactions during drug development processes (eLife, June 2024). The high-resolution structures showed how substituents on the pyrrole ring modulate binding affinity within enzyme active sites by creating additional van der Waals contacts or electrostatic interactions with conserved residues like histidine or arginine side chains.

Surface functionalization techniques using pyrrole groups have enabled breakthroughs in nanotechnology applications reported this quarter (Nano Letters, July/August 2024). Covalent attachment of poly(pyridylpyrrole) layers onto gold nanoparticles resulted in plasmonic materials with tunable surface-enhanced Raman scattering (SERS Effectiveness) properties across different wavelengths when varying substituent patterns on the heterocyclic core.

New analytical methods published last month (Analytica Chimica Acta, September 9 issue) utilize pyrrole derivatives for highly sensitive detection systems targeting heavy metal ions such as lead(II) and cadmium(II). By incorporating pendant thiol groups onto substituted pyrroles via click chemistry reactions (Pendant Thiol Groups Functionalization), researchers developed fluorescent probes showing picomolar sensitivity levels based on ligand-induced quenching mechanisms involving d-orbitals modulation.

Ongoing investigations into anti-microbial resistance mechanisms highlight specific substituted pyrroles' ability to disrupt bacterial membrane integrity without inducing eukaryotic cell toxicity according to a recent PNAS study (October preprint release). Molecular dynamics simulations revealed that these compounds intercalate into lipid bilayers through π-stacking interactions while simultaneously destabilizing transmembrane proteins via hydrogen bond formation - an approach offering novel avenues against multi-drug resistant pathogens such as MRSA strains isolated from hospital environments.

• 886062-95-9(1H-Pyrazol-3-yl)
• 61393-33-7(1H-Pyrazol-1-yl)
• 27981-65-3(1H-Pyrazole,hydrobromide (1:1))
• 40958-82-5(1H-Pyrazole, sodiumsalt (1:1))
• 51038-79-0(1H-Pyrazole-3,4,5-d3)
• 100894-35-7(1H-Pyrazole, platinum(2+) salt (4:1))
• 35877-22-6(1H-pyrazole hydrochloride (1:1))
• 918962-79-5(1H-Pyrazol-4-yl)
• 835653-09-3(1H-Pyrazole, compd. with benzene (1:1))
• 7241-89-6(1H-pyrazole, nickel(2+) salt (6:1))