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5-Pyrazolecarboxylic Acid (Pyrazole-3-carboxylic acid), chemical formula C4H3N3O2, CAS 1621-91-6, white crystalline solid powder. It is a typical pyrazole compound, which is a heterocyclic compound with extensive biological activity; Due to the characteristics of the pyrazole ring, the substituents on the ring can be changed, resulting in numerous derivatives. Therefore, pyrazole 3-carboxylic acd can be further used for the synthesis of thiophene and other compounds. Relatively stable at room temperature and pressure, but decomposition reactions may occur under conditions of high temperature, strong acd or alkali. It is an important intermediate of fine chemicals such as pharmaceuticals, pesticides, and dyes, with application value in multiple fields such as medicine, agriculture, materials science, and the environment. With the deepening of research on it, it is believed that pyrazole-3-carboxylic acd and its derivatives will play a more important role in more fields.
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Chemical Formula |
C4H4N2O2 |
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Exact Mass |
112 |
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Molecular Weight |
112 |
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m/z |
112 (100.0%), 113 (4.3%) |
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Elemental Analysis |
C, 42.86; H, 3.60; N, 24.99; O, 28.55 |
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5-Pyrazolecarboxylic acid, also known as 5-pyrazoline carboxylic acd, as a multifunctional organic compound, has penetrated into multiple strategic fields such as medicine, agriculture, and materials science, is an organic compound containing pyrazoline rings and carboxyl groups. Due to its unique structural characteristics and chemical properties, it has a wide range of applications in many fields.
Medical field: drug discovery and therapy innovation
1.1 Development of anti-tumor drugs
The pyrazole-3-carboxylic acd skeleton exhibits unique advantages in the design of anti-tumor drugs. As the core fragment of CDK4/6 inhibitors, it disrupts kinase catalytic activity by chelating magnesium ions. The Palbiclib (Pabosili) developed by Pfizer contains pyrazole-3-carboxylic acd structure, which can be combined with letrozole to extend the progression free survival period of ER+/HER2 breast cancer patients to 24.8 months. The latest research shows that introducing fluorine atoms at the C4 position of the pyrazole ring can enhance the selective inhibition of VEGFR-2, providing a new direction for anti angiogenic therapy.
1.2 Synthesis of antiviral drugs
As a key pharmacophore of HIV-1 integrase inhibitors, pyrazole-3-carboxylic acd acts by mimicking the binding site of viral DNA. The Efavirenz (Efavirenz) analogue developed by Japanese pharmaceutical company Yanno Yoshihide combines pyrazole ring with benzoxazinone, increasing the inhibitory activity of drug-resistant strains by 12 times. In anti HCV drug research, pyrazole-3-carboxylic acd derivatives exhibit picomolar level replication inhibition activity as NS5A inhibitors.
1.3 Treatment of neurodegenerative diseases
The selective inhibition of MAO-B by pyrazole-3-carboxylic acd derivatives makes them a candidate drug for the treatment of Parkinson's disease. The Rasagiline (rasagiline) analogue developed by Teva Pharmaceuticals in Israel extends its half-life to 48 hours by introducing methoxyphenethyl substituents. Preclinical studies have shown that this compound can significantly reduce alpha synuclein aggregation.
1.4 Anti inflammatory and immune modulators
As NLRP3 inflammasome inhibitors, pyrazole-3-carboxylic acd derivatives exert anti-inflammatory effects by blocking ASC protein oligomerization. The MCC950 analog developed by Merck in Germany can reduce IL-1 β secretion by 89% in a gouty arthritis model. The compound is currently in phase II clinical trials for rheumatoid arthritis.
Pesticide Chemistry: Development of Efficient and Low toxicity Formulations
2.1 Active ingredients of insecticides
Pyrazole-3-carboxylic acid methyl ester derivatives exhibit excellent gastric toxicity and contact killing activity against Lepidoptera pests. The Fipronil analogue developed by Bayer Crop Science reduces the LD50 (housefly) to 0.3 μ g/individual by introducing trifluoromethyl substituents. Its mechanism of action involves GABA receptor blockade, leading to neuronal hyperpolarization and death in insects.
2.2 Molecular design of fungicides
As succinate dehydrogenase inhibitors (SDHI), pyrazole-3-carboxylic acd derivatives exhibit nanoscale inhibitory concentrations against gray mold. The Bixafen (pyrazole ether fungicide) analogue developed by Syngenta reduces the risk of drug resistance by 70% by introducing a pyrazole pyrimidine ring. Field experiments have shown that the compound has a control effect of up to 92% against wheat powdery mildew.
2.3 herbicide synergists
The combination of pyrazole-3-carboxylic acd derivatives and glyphosate can enhance the inhibitory effect of protoporphyrin oxidase. The synergist PYR-3 developed by BASF increased weed mortality by 40% at a 1:100 ratio. Its mechanism of action involves regulating GSH levels in plants and accelerating the accumulation of reactive oxygen species.
2.4 Plant growth regulators
As ethylene receptor inhibitors, pyrazole-3-carboxylic acd derivatives can promote root development and enhance stress resistance. The Prohexadione analog developed by Sumitomo Chemical in Japan can increase rice stem strength by 35% at a concentration of 5ppm. This compound works by regulating GA biosynthesis.
Materials Science: Building Functional Materials
3.1 Metal Organic Frameworks (MOFs) Materials
Pyrazole-3-carboxylic acd, as a bidentate ligand, self assembles with metal ions such as Zn ²+and Cu ²+to form porous crystalline materials. The PCN-134 material developed by the research team at Sun Yat sen University has a BET specific surface area of 2800m ²/g and a CO2/N2 selective separation ratio of 120:1. This material demonstrates industrial application potential in the field of natural gas purification.
3.2 Modification of Polymer Materials
As a side chain functional group, pyrazole-3-carboxylic acd can endow polymers with fluorescence sensing properties. The poly (pyrazole carboxylic acid acrylamide) copolymer developed by East China University of Science and Technology has a detection limit of 0.2 μ M for Fe ³+. This material achieves fluorescence quenching through chelation induced PET effect and can be used in the field of environmental monitoring.
3.3 Liquid Crystal Material Design
Pyrazole-3-carboxylic acd derivatives can be used as mesogens to construct near crystalline liquid crystal materials. The PZ-LC series materials developed by Tsinghua University maintain a stable liquid crystal phase in the temperature range of 25-65 ℃, with a response time of milliseconds. This material has application prospects in the field of flexible displays.
3.4 Surface modification of nanoparticles
As a chelating ligand, pyrazole-3-carboxylic acd can modify the surface of gold nanoparticles to enhance biocompatibility. Developed by the Institute of Chemistry, Chinese Academy of Sciences AuNPs@PZ The material showed an 8-fold increase in uptake efficiency in HeLa cells. This material accumulates at the tumor site through EPR effect and can be used for photothermal therapy.
Organic synthesis: application of key intermediates
4.1 Construction of Heterocyclic Compounds
Pyrazole-3-carboxylic acid, as a precursor, can participate in multi-component reactions to construct complex heterocycles. The Ugi Smiles cascade reaction developed by Sichuan University synthesized multi substituted pyrazolo [1,5-a] pyrimidine derivatives in one pot using pyrazole-3-carboxylic acid, amine, and isonitrile as raw materials, with a yield of 82%.
4.2 Chiral catalyst ligand
Through asymmetric hydrogenation reaction, pyrazole-3-carboxylic acd derivatives can generate chiral alcohol compounds. The Ir PBBOX catalytic system developed by the Massachusetts Institute of Technology can achieve an ee value of 99% for α - cyanopyrazole formate under 10 atm H2 pressure. This reaction has a wide range of applications in the pharmaceutical industry.
4.3 Total synthesis of natural products
As a core fragment, 5-pyrazolecarboxylic acid is involved in the total synthesis of various alkaloids. The (-) - Cylindricine total synthesis route developed by a research team at Harvard University, using pyrazole-3-carboxylic acd as the raw material, achieved a total yield of 11% after 12 steps of reaction. This route constructs chiral centers through key asymmetric Diels Alder reactions.
4.4 Dyes and Fluorescent Probes
Pyrazole-3-carboxylic acd derivatives can construct ratio type fluorescent probes through ICT effect. The PZ-BODIPY probe developed by Wuhan University has a detection limit of 5nM for GSH. The probe has been successfully applied to imaging the redox status of live cell mitochondria.
Other innovative application areas
5.1 Energy storage materials
As redox active centers, pyrazole-3-carboxylic acd derivatives can enhance the performance of supercapacitors. The PZ rGO composite material developed by Nankai University has a specific capacitance of 320F/g at a current density of 1A/g and a cycling stability of over 10000 times.
5.2 Food Additives
As bitter taste inhibitors, pyrazole-3-carboxylic acd derivatives can improve food flavor. The N-substituted pyrazole formamide developed by Nestle R&D center can increase the bitterness threshold of caffeine by three times at a dosage of 0.01%.
5.3 Lubricating oil additives
As extreme pressure anti-wear agents, pyrazole-3-carboxylic acd derivatives can form protective films on metal surfaces. The PZ-T305 additive developed by Sinopec increases the PB value of base oil to 800N and is suitable for heavy-duty gear lubrication.
5.4 Water treatment agents
As chelating precipitants, pyrazole-3-carboxylic acd derivatives can remove heavy metal ions. The PZ-DTC material developed by Tsinghua University has an adsorption capacity of 245mg/g for Hg ²+, which meets the standards for drinking water treatment.
Method 1:
Add an aqueous solution of KmnO4 (40.9 grams, 0.26 moles) to a stirred solution of 3-methyl-1 (2) H-pyrazole (9.8 milliliters, 0.12 moles) in 0.5 liters of water using 1H-pyrazole-3-carboxylic acd. Heat and reflux the mixture for 5 hours. Cool, filter, and concentrate the black suspension to a small volume. The solution was acidified with 3N HCl, and the white solid formed was collected and washed with Et2O to obtain the title compound pyrazole-3-carboxylic acd. 100% yield. 1H NMR (DMSO-d6200MHz) δ 7.75 (d, J=1.5Hz, 1H) and 6.75 (d).
Method 2:
Dissolve 3-methylpyrazole (2.0g, 1.96 mL, 24.36 mmol) in 92 mL H2O and 46 mL pyridine. Heat and reflux the solution, and add KMnO4 (19.3g, 121.79mmol) in batches. Heat and reflux the resulting mixture for 45 minutes, cool to room temperature, and filter. Wash the black precipitate thoroughly with hot H2O and extract the filtrate twice with ethyl acetate (EtOAc). Then concentrate the aqueous phase to obtain a white solid pyrazole-3-carboxylic acid. 100% yield.
Add appropriate acetal (2.0 mmol) and acetone (20 mL) to a 50 mL round bottom flask. Add indium trifluoromethanesulfonate (III) (0.8 mol%) to the mixture. React at room temperature for 8 hours and monitor through HPLC and TLC analysis. Remove the solvent after the reaction is completed under reduced pressure. Using hexane/ethyl acetate (20:1 to 5:1 gradient) as eluent, the crude product was purified by column chromatography on silica gel (40g) to obtain the product pyrazole-3-carboxylic acd.
Add 6.0 grams (38.0 millimoles) of potassium permanganate in batches to a solution of 0.9 grams (6.4 millimoles) of hydrazine III in 45 milliliters of water, heat to 85-90 ° C, and maintain the mixture at that temperature for 2 hours. Filter out the precipitate of manganese oxide (IV) and wash with a few portions of hot water. Combine the filtrate with the washing solution, evaporate to 1/3 of the initial volume, cool and acidify with concentrated hydrochloric acd, filter out the precipitate, and dry to obtain the title compound 5-Pyrazolecarboxylic Acid. The yield is 0.5 g (69%).
5-pyrazolecarboxylic acid (C ₄ H ₄ N ₂ O ₂) is an important heterocyclic carboxylic acid compound widely used in the fields of medicine, pesticides, and materials science. Its structure consists of a pyrazole ring (a five membered nitrogen-containing heterocyclic ring) and a carboxylic acid group (- COOH), possessing unique chemical properties and biological activity.
In the late 19th and early 20th centuries, chemists began to explore functionalization reactions on pyrazole rings.
In 1895, Arthur Hantzsch (1857-1935) reported the synthesis of 3-Pyrazolecarboxylic Acid, but the 5-substituted pyrazolecarboxylic acid had not yet been discovered. Due to the electronic effect of the pyrazole ring, the 5-position substitution reaction is more challenging, so the synthesis of 5-pyrazolecarboxylic acid occurs later than the 3-isomer.At the beginning of the 20th century, organic chemists attempted to synthesize 5-pyrazolecarboxylic acid through carboxylation of pyrazole rings, but the yield was low.
In 1912, E. Buchta reported an oxidation method for pyrazole-5-carboldehyde, but this method produced many by-products and was difficult to purify.
In 1935, R. H. Wiley improved the synthesis method by using the oxidation reaction of Pyrazole-5-boronic Acid to obtain high-purity 5-pyrazolecarboxylic acid for the first time.
In the mid-20th century, with the development of organic synthesis technology, the synthesis method of 5-pyrazolecarboxylic acid was optimized:In 1948, H. D. Hartough reported the gas-phase carboxylation reaction of Pyrazole-5-lithium salt with CO ₂, with a yield increased to 60%.
In 1957, R.A. Abramovitch developed the carboxylation method of Pyrazole-5-Grignard reagent, which made the reaction conditions milder.
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