6647-93-4

Usage

Uses

Used in Pharmaceutical Industry:
4-IODO-PYRAZOLE-3-CARBOXYLIC ACID is used as an inhibitor for human 15-lipoxygenase-1, which plays a crucial role in various inflammatory and allergic responses. By inhibiting this enzyme, it can potentially be employed in the development of treatments for conditions such as asthma, arthritis, and other inflammatory diseases.
Used in Antibacterial Applications:
4-IODO-PYRAZOLE-3-CARBOXYLIC ACID is used as an antibacterial agent due to its oxadiazole structure, which contributes to its ability to combat bacterial infections. This property makes it a valuable compound in the development of new antibiotics, particularly in the face of increasing antibiotic resistance.
Used in Chemical Research:
As a white solid with unique chemical properties, 4-IODO-PYRAZOLE-3-CARBOXYLIC ACID can be utilized in various chemical research applications. It can serve as a starting material or intermediate in the synthesis of more complex molecules, potentially leading to the discovery of new drugs or materials with novel properties.

Upstream product

• 2033-45-6 4-iodo-3,5-dimethyl-1H-pyrazole 
• 1621-91-6 1H-pyrazole-3-carboxylic acid 
• 15802-75-2 3-iodo-2-methyl-1H-pyrazole 

Downstream Products

• 950482-93-6 C₁₁H₁₁N₄O₂I 
• 1021419-15-7 4-iodo-1H-pyrazole-3-carboxylic acid (2-amino-5-methoxy-phenyl)-amide 

Relevant academic research and scientific papers

New approach to electrochemical iodination of arenes exemplified by the synthesis of 4-iodopyrazoles of different structures

The two-stage electrosynthesis of 4-iodosubstituted pyrazole derivatives was performed. At the first stage, KIO3 was obtained at the Ni anode under the undivided galvanostatic conditions of electrolysis of an aqueous alkaline solution of KI (or I2) at the Ni anode. At the second stage, pyrazole and its derivatives were iodinated in the heterophase (H2O-CHCl3 (CCl4)) medium by the KIO3-KI (or KIO3-I2) system in the presence of H2SO4. The yields of iodopyrazoles were 74-92%. The electrochemical iodination of anisole, 2-methylpyrazole, and thiophene was carried out to form 4-iodoanisole (88% yield), 4,5-diiodo-2-methylimidazole (54% yield), and a mixture of 2-iodothiophene (60% yield) and 2,5-diiodothiophene (4% yield).

Efficient iodination of structurally varying pyrazoles in heterophase medium

A synthesis of 4-iodo-substituted pyrazoles by iodination of pyrazole and its derivatives in the heterophase (H2O/CHCl3 (CCl 4)) medium with the system KI-KIO3 in the presence of H2SO4 additives was accomplished. The yields of 4-iodo-substituted pyrazoles in the iodination of pyrazole, 3,5- dimethylpyrazole, pyrazole-3(5)-carboxylic acid, 1-methylpyrazole-3-carboxylic acid, 1-methylpyrazole-5-carboxylic acid, 3-nitropyrazole, 1-methyl-3- nitropyrazole, 1-methylpyrazole, 1-ethylpyrazole, and 1-isopropylpyrazole were within 80-97%, whereas in the case of 3-nitropyrazole-5-carboxylic acid it was 32%.

Electrosynthesis of 4-iodopyrazole and its derivatives

Electrosynthesis of 4-iodo-substituted pyrazoles has been accomplished by iodination of the corresponding precursors on a Pt-anode in aqueous solutions of KI under conditions of the diaphragm galvanostatic electrolysis. Efficiency of the process depends on the donor-acceptor properties of substituents and their positions in the pyrazole ring. Thus, iodination of pyrazole, 3,5-dimethylpyrazole, 3-nitropyrazole, 1-methylpyrazole, 1,3-dimethylpyrazole, pyrazole-3(5)-carboxylic acid or methyl esters furnished 4-iodo derivatives in 57, 86, 2, 5, 35, 30, and 40% yields, respectively.

Micelle Activated Reactions I. Micelle Activated Iodination and Partial Dehalogenation of Pyrazoles and 1,2,4-Triazoles

A method is described to iodinate pyrazole, substituted pyrazoles or 1,2,4-triazole with iodine or iodine chloride in aqueous alkaline in the presence of an anionic surfactant. 4-Iodo- (2a), 4-iodo-3(5)-methyl- (2b), 3(5),4-diiodo- (3a), 3(5),4-diiodo-5(3)-methyl- (3b), and 3,4,5-triiodo-pyrazole (3d) as soon as 4-iodo-pyrazole-3(5)-carboxylic acid (2c), and 3(5)-iodo-1,2,4-triazole (5) were prepared.Anhydrous hydrogen fluoride or triethylamine trishydrofluoride were found to be a suitable agent to effect a regioselective partial dehalogenation of 3b, 3d and 3,5-dibromo-1,2,4-triazole (7).We prepared 3(5)-iodo-5(3)-methyl-pyrazole (6b), 3,5-diiodo-pyrazole (6d) and 3(5)-bromo-1,2,4-triazole (8) on this way.