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Introduction to 1-Methyl-3-phenyl-1H-pyrazole-5-carbaldehyde (CAS No. 864068-96-2)

1-Methyl-3-phenyl-1H-pyrazole-5-carbaldehyde, identified by its Chemical Abstracts Service (CAS) number 864068-96-2, is a heterocyclic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal research. This compound belongs to the pyrazole family, a class of heterocycles characterized by a five-membered ring containing two nitrogen atoms. The presence of a formyl group (aldehyde) at the 5-position and a methyl substituent at the 1-position, along with a phenyl group at the 3-position, imparts unique chemical and biological properties that make it a promising candidate for further investigation.

The structure of 1-Methyl-3-phenyl-1H-pyrazole-5-carbaldehyde exhibits a conjugated system due to the interaction between the aldehyde group and the aromatic ring. This conjugation not only influences its electronic properties but also enhances its reactivity, making it suitable for various synthetic transformations. The compound’s molecular formula is C₉H₉N₃O, reflecting its composition of carbon, hydrogen, nitrogen, and oxygen atoms.

In recent years, there has been growing interest in pyrazole derivatives due to their diverse biological activities. Pyrazoles have been reported to exhibit antimicrobial, anti-inflammatory, antitumor, and antioxidant properties. Among these derivatives, 1-Methyl-3-phenyl-1H-pyrazole-5-carbaldehyde stands out due to its unique substitution pattern, which may contribute to its biological efficacy. The aldehyde functionality provides a site for further chemical modification, allowing for the synthesis of more complex derivatives with tailored properties.

One of the most compelling aspects of 1-Methyl-3-phenyl-1H-pyrazole-5-carbaldehyde is its potential application in drug discovery. The pyrazole core is a common scaffold in many pharmacologically active compounds, and modifications at different positions on this ring can lead to significant changes in biological activity. For instance, studies have shown that substituents at the 3-position can influence binding affinity to biological targets. The phenyl group in this compound may enhance interactions with certain enzymes or receptors, making it a valuable building block for medicinal chemists.

Recent research has explored the synthetic pathways for 1-Methyl-3-phenyl-1H-pyrazole-5-carbaldehyde, highlighting its accessibility through various multi-step reactions. One such approach involves the condensation of 3-bromopyridine with methyl acetoacetate under basic conditions, followed by formylation at the 5-position. These synthetic strategies demonstrate the feasibility of producing this compound in sufficient quantities for both laboratory studies and potential industrial applications.

The chemical reactivity of 1-Methyl-3-phenyl-1H-pyrazole-5-carbaldehyde is another area of interest. The aldehyde group can participate in various reactions, including condensation reactions with amino compounds to form Schiff bases, which are known for their biological activity. Additionally, the compound can undergo reduction to yield an alcohol or further oxidation to form a carboxylic acid derivative. These transformations provide chemists with multiple avenues for developing new analogs with enhanced properties.

Beyond its synthetic utility, 1-Methyl-3-phenyl-1H-pyrazole-5-carbaldehyde has shown promise in preliminary biological assays. Studies have indicated that it may exhibit inhibitory effects on certain enzymes implicated in inflammatory diseases and cancer. The exact mechanism of action remains under investigation, but preliminary data suggest that its interaction with biological targets could lead to therapeutic benefits. Further research is needed to fully elucidate its pharmacological profile and potential clinical applications.

The development of new pharmaceuticals often relies on high-throughput screening (HTS) methods to identify compounds with desirable biological activities. 1-Methyl-3-phenyl-1H-pyrazole-5-carbaldehyde could serve as a hit compound in such screens due to its unique structure and potential bioactivity. Its suitability for HTS is enhanced by its well-defined chemical properties and synthetic accessibility. Once identified as a hit, it can be optimized through structure-based drug design or de novo design approaches to improve potency and selectivity.

The role of computational chemistry in drug discovery cannot be overstated. Molecular modeling techniques can be employed to predict the binding affinity of 1-Methyl-3-phenyl-1H-pyrazole-5-carbaldehyde to potential targets such as enzymes or receptors. These predictions can guide experimental efforts by identifying key interactions and suggesting modifications that could enhance biological activity. Additionally, virtual screening methods can help identify additional derivatives of this compound that may exhibit improved properties.

In conclusion, 1-Methyl -3 - phenyl - 1 H - pyrazole - 5 - carbaldehyde (CAS No .864068 -96 -2 ) is a versatile heterocyclic compound with significant potential in pharmaceutical research . Its unique structural features , synthetic accessibility , and preliminary biological activity make it an attractive candidate for further investigation . As research continues , this compound may contribute valuable insights into drug discovery and development , offering new opportunities for therapeutic intervention .

• 10250-60-9(1,5-dimethyl-3-phenyl-1H-pyrazole)
• 10250-58-5(1,3-dimethyl-5-phenyl-1H-pyrazole)
• 124344-94-1(1-methyl-5-phenyl-1H-pyrazole-3-carbaldehyde)
• 10250-64-3(1-Methyl-3-phenyl-1H-pyrazole-5-carboxylic acid)
• 179056-79-2(3-(1-methyl-1h-pyrazol-3-yl)benzaldehyde)
• 87838-35-5(1H-Pyrazole-5-carboxaldehyde, 1,3-diphenyl-)
• 179056-80-5(Benzaldehyde,3-(1-methyl-1H-pyrazol-5-yl)-)
• 179055-27-7(4-(1-Methyl-1H-pyrazol-3-YL)benzaldehyde)
• 179055-28-8(4-(1-Methyl-1H-pyrazol-5-yl)benzaldehyde)
• 864068-95-1(1H-Pyrazole-5-carbonylchloride, 1-methyl-3-phenyl-)