51660-65-2

Usage

Uses

Used in Pharmaceutical Applications:
4-IODO-1,3,5-TRIMETHYL-1H-PYRAZOLE is used as a pharmaceutical intermediate for the synthesis of various drugs. Its unique structure allows it to be a key component in the development of new medications, particularly those targeting specific biological pathways or receptors.
Used in Agricultural Applications:
In agriculture, 4-IODO-1,3,5-TRIMETHYL-1H-PYRAZOLE is used as a chemical component in the formulation of agrochemicals. Its properties may contribute to the development of pesticides, herbicides, or other products aimed at enhancing crop protection and yield.
Used in Research and Development:
4-IODO-1,3,5-TRIMETHYL-1H-PYRAZOLE serves as a valuable research compound in scientific studies. It is utilized to explore new chemical reactions, investigate its potential biological activities, and understand its interactions with various molecular targets, which can lead to the discovery of novel applications and uses in different industries.

InChI:InChI=1/C6H9IN2/c1-4-6(7)5(2)9(3)8-4/h1-3H3

Upstream product

• 1072-91-9 1,3,5-trimethyl-1H-pyrazole 
• 67-51-6 3,5-dimethyl-1H-pyrazole 
• 2033-45-6 4-iodo-3,5-dimethyl-1H-pyrazole 
• 74-88-4 methyl iodide 
• 123-54-6 acetylacetone 

Downstream Products

• 22779-02-8 4-ethynyl-1,3,5-trimethyl-1H-pyrazole 

Relevant academic research and scientific papers

Predicting the catalytic activity of azolium-based halogen bond donors: an experimentally-verified theoretical study

This report demonstrates the successful application of electrostatic surface potential distribution analysis for evaluating the relative catalytic activity of a series of azolium-based halogen bond donors. A strong correlation (R2> 0.97) was observed between the positive electrostatic potential of the σ-hole on the halogen atom and the Gibbs free energy of activation of the model reactions (i.e., halogen abstraction and carbonyl activation). The predictive ability of the applied approach was confirmed experimentally. It was also determined that the catalytic activity of azolium-based halogen bond donors was generally governed by the structure of the azolium cycle, whereas the substituents on the heterocycle had a limited impact on the activity. Ultimately, this study highlighted four of the most promising azolium halogen bond donors, which are expected to exhibit high catalytic activity.

Deprotonation of 4-ethynylpyrazolium salts

4-Ethynyl-1,2-dimethylpyrazolium salts were prepared by methylation of the corresponding 4-ethynyl-1-methylpyrazoles with trimethyloxonium tetrafluoroborate and were deprotonated to give the corresponding pyrazolium-4acetylenides, which are mesomeric betaines. These can be represented as alkynyl- or mesoionic allenylidene-type resonance forms. Calculations and spectroscopic investigations were performed to determine the contribution of each canonical form to the overall structure. Ylides and N-heterocyclic carbenes are tautomers of the betaines. Their relative stabilities have been compared.

A simple method for iodination of heterocyclic compounds using HIO 4/NaCl/silica gel/H2SO4 in water

A fast and simple method for iodination of some heterocycles is reported. The reactions were carried out in water, using HIO4/H 2SO4/NaCl/silica gel at moderate temperatures of 25-50 °C. Springer-Verlag 2011.

Green iodination of pyrazoles with iodine/hydrogen peroxide in water

In this Letter, we describe a practical, green iodination of pyrazoles to form the corresponding 4-iodopyrazole derivatives. The reaction takes place in water, using only 0.5 equiv of iodine and 0.6 equiv of hydrogen peroxide, a system that generates water as the only reaction by-product.

A mild and efficient method for halogenation of 3,5-dimethyl pyrazoles by ultrasound irradiation using N-halosuccinimides

The 4-halo-3,5-dimethyl pyrazoles have been synthetisized in good yields in short reaction times in the absence of a catalyst by reaction of 3,5-dimethyl pyrazoles with N-halosuccinimides (NBS, NCS and NIS) under ultrasound irradiation. Finally, the halogenation of pyrazoles with Br2, IC1 and I2 was showed in similar conditions.