Production Method 1

916791-97-4

83405-71-4

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Methanol ,  Water ;  2 h, rt

Reference

Pyrazole C-region analogues of 2-(3-fluoro-4-methylsulfonylaminophenyl)propanamides as potent TRPV1 antagonists

Lee, Sunho; et al, Bioorganic & Medicinal Chemistry Letters, 2017, 27(18), 4383-4388

Production Method 2

83405-71-4

Reaction Conditions

1.1 Reagents: Lithium bis(trimethylsilyl)amide Solvents: Tetrahydrofuran ;  overnight, -78 °C → rt
2.1 Reagents: Triethylamine ,  Hydrazine, dihydrochloride Solvents: Ethanol ;  2 h, rt
3.1 Reagents: Sodium hydroxide Solvents: Methanol ,  Water ;  2 h, rt

Reference

Pyrazole C-region analogues of 2-(3-fluoro-4-methylsulfonylaminophenyl)propanamides as potent TRPV1 antagonists

Lee, Sunho; et al, Bioorganic & Medicinal Chemistry Letters, 2017, 27(18), 4383-4388

Production Method 3

13395-36-3

83405-71-4

Reaction Conditions

1.1 Reagents: Triethylamine ,  Hydrazine, dihydrochloride Solvents: Ethanol ;  2 h, rt
2.1 Reagents: Sodium hydroxide Solvents: Methanol ,  Water ;  2 h, rt

Reference

Pyrazole C-region analogues of 2-(3-fluoro-4-methylsulfonylaminophenyl)propanamides as potent TRPV1 antagonists

Lee, Sunho; et al, Bioorganic & Medicinal Chemistry Letters, 2017, 27(18), 4383-4388

Production Method 4

83405-71-4

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Solvents: Ethanol
1.2 Reagents: Hydrazine hydrate (1:1)
1.3 Reagents: Sodium hydroxide Solvents: Water

Reference

Agonist lead identification for the high affinity niacin receptor GPR109a

Gharbaoui, Tawfik; et al, Bioorganic & Medicinal Chemistry Letters, 2007, 17(17), 4914-4919

Production Method 5

83405-70-3

83405-71-4

Reaction Conditions

1.1 Reagents: Sodium hydroxide

Reference

3-Substituted pyrazoles and 4-substituted triazoles as inhibitors of human 15-lipoxygenase-1

Pelcman, Benjamin; et al, Bioorganic & Medicinal Chemistry Letters, 2015, 25(15), 3024-3029

5-tert-butyl-1H-pyrazole-3-carboxylic acid Raw materials

• Ethyl 5-tert-butyl-1h-pyrazole-3-carboxylate
• Ethyl 5,5-dimethyl-2,4-dioxohexanoate
• Ethyl 3-tert-butyl-1H-pyrazole-5-carboxylate

5-tert-butyl-1H-pyrazole-3-carboxylic acid Preparation Products

• 5-tert-butyl-1H-pyrazole-3-carboxylic acid (83405-71-4)

• 1. Evidence of CO2 molecule acting as an electron acceptor on a nanoporous metal–organic-framework MIL-53 or Cr3+(OH)(O2C–C6H4–CO2)?
  Alexandre Vimont,Arnaud Travert,Philippe Bazin,Jean-Claude Lavalley,Marco Daturi,Christian Serre,Gérard Férey,Sandrine Bourrelly,Philip L. Llewellyn Chem. Commun., 2007, 3291-3293
• 2. Fe/Fe3C@C nanoparticles encapsulated in N-doped graphene–CNTs framework as an efficient bifunctional oxygen electrocatalyst for robust rechargeable Zn–air batteries?
  Zhiyan Chen,Nan Wu,Yaobing Wang,Bing Wang,Yingde Wang J. Mater. Chem. A, 2018,6, 516-526
• 3. Evolutionary approaches in protein engineering towards biomaterial construction
  Brindha J.,Balamurali M. M.,Kaushik Chanda RSC Adv., 2019,9, 34720-34734
• 4. Fe(iii)-mediated isomerization of α,α-diarylallylic alcohols to ketones via radical 1,2-aryl migration?
  Ziyang Deng,Changwei Chen,Sunliang Cui RSC Adv., 2016,6, 93753-93755
• 5. Fe(ii)-Assisted one-pot synthesis of ultra-small core–shell Au–Pt nanoparticles as superior catalysts towards the HER and ORR?
  Yi Cao,Yujiao Xiahou,Lixiang Xing,Xiang Zhang,Hong Li,ChenShou Wu,Haibing Xia Nanoscale, 2020,12, 20456-20466

5-Tert-butyl-1H-pyrazole-3-carboxylic Acid (CAS No. 83405-71-4)

The compound 5-Tert-butyl-1H-pyrazole-3-carboxylic Acid (CAS No. 83405-71-4) is a highly specialized organic compound with significant applications in various fields of chemistry and pharmacology. This compound belongs to the class of pyrazoles, which are five-membered aromatic heterocycles containing two adjacent nitrogen atoms. The presence of the tert-butyl group at the 5-position and the carboxylic acid group at the 3-position imparts unique chemical properties, making it a valuable intermediate in synthetic chemistry.

Recent studies have highlighted the importance of pyrazole derivatives in drug discovery, particularly in the development of kinase inhibitors and other bioactive molecules. The tert-butyl substituent in this compound contributes to its lipophilicity, enhancing its ability to interact with biological targets. Moreover, the carboxylic acid group provides versatility in chemical modifications, enabling the synthesis of various esters, amides, and other derivatives that can be tailored for specific applications.

One of the most notable advancements involving 5-Tert-butyl-1H-pyrazole-3-carboxylic Acid is its role as a key intermediate in the synthesis of anti-cancer agents. Researchers have demonstrated that derivatives of this compound can inhibit key enzymes involved in cancer cell proliferation, making it a promising candidate for further exploration in oncology. Additionally, its use in agricultural chemistry has been explored, with studies showing potential as a fungicide or plant growth regulator.

The synthesis of 5-Tert-butyl-1H-pyrazole-3-carboxylic Acid typically involves multi-step reactions, often starting from readily available starting materials such as aldehydes or ketones. The incorporation of the tert-butyl group is achieved through alkylation or acylation reactions, while the carboxylic acid functionality is introduced via oxidation or direct synthesis methods. Recent optimizations in these synthetic pathways have improved yields and reduced production costs, making this compound more accessible for large-scale applications.

In terms of physical properties, 5-Tert-butyl-1H-pyrazole-3-carboxylic Acid exhibits a melting point of approximately 220°C and is sparingly soluble in common organic solvents. Its stability under various conditions has been thoroughly investigated, with results indicating excellent thermal stability and resistance to hydrolysis under mild conditions.

The demand for pyrazole-based compounds has surged due to their widespread use in pharmaceuticals, agrochemicals, and materials science. As a result, 5-Tert-butyl-1H-pyrazole-3-carboxylic Acid has become a focal point for researchers seeking to develop novel bioactive molecules with enhanced efficacy and selectivity.

In conclusion, 5-Tert-butyl-1H-pyrazole-3-carboxylic Acid (CAS No. 83405-71-4) stands out as a versatile and valuable compound with immense potential across multiple disciplines. Its unique structure, combined with recent advancements in synthetic methods and biological applications, positions it as a cornerstone for future innovations in chemical research.

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