Cas no 524740-33-8 (5-chloro-3-(chloromethyl)-1-methyl-1H-pyrazole)

5-Chloro-3-(chloromethyl)-1-methyl-1H-pyrazole is a halogenated pyrazole derivative with significant utility in synthetic organic chemistry. Its reactive chloromethyl group enables facile functionalization, making it a versatile intermediate for the synthesis of agrochemicals, pharmaceuticals, and specialty chemicals. The compound's stability under standard conditions ensures reliable handling and storage. Its dual chloro-substitution enhances electrophilic reactivity, facilitating nucleophilic substitution reactions to yield diverse derivatives. The methyl group at the 1-position further contributes to its stability and selectivity in transformations. This compound is particularly valued for its role in constructing heterocyclic frameworks, offering a balance of reactivity and structural modularity for advanced chemical synthesis.
5-chloro-3-(chloromethyl)-1-methyl-1H-pyrazole structure
524740-33-8 structure
Product Name:5-chloro-3-(chloromethyl)-1-methyl-1H-pyrazole
CAS No:524740-33-8
MF:C5H6Cl2N2
MW:165.020538806915
MDL:MFCD18381882
CID:871010
PubChem ID:12035664
Update Time:2025-08-05

5-chloro-3-(chloromethyl)-1-methyl-1H-pyrazole Chemical and Physical Properties

Names and Identifiers

    • 1H-PYRAZOLE, 5-CHLORO-3-(CHLOROMETHYL)-1-METHYL
    • 1H-Pyrazole,5-chloro-3-(chloromethyl)-1-methyl-(9CI)
    • 5-Chloro-3-(chloromethyl)-1-methyl-1H-pyrazole
    • 5-chloro-3-(chloromethyl)-1-methyl-1H-pyrazole
    • MDL: MFCD18381882
    • Inchi: 1S/C5H6Cl2N2/c1-9-5(7)2-4(3-6)8-9/h2H,3H2,1H3
    • InChI Key: VIYVHOHOCBLPMU-UHFFFAOYSA-N
    • SMILES: ClC1=CC(CCl)=NN1C

Computed Properties

  • Exact Mass: 163.9908036g/mol
  • Monoisotopic Mass: 163.9908036g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 9
  • Rotatable Bond Count: 1
  • Complexity: 99
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.6
  • Topological Polar Surface Area: 17.8?2

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Additional information on 5-chloro-3-(chloromethyl)-1-methyl-1H-pyrazole

Introduction to 5-chloro-3-(chloromethyl)-1-methyl-1H-pyrazole (CAS No. 524740-33-8)

5-chloro-3-(chloromethyl)-1-methyl-1H-pyrazole, identified by the CAS number 524740-33-8, is a significant compound in the field of pharmaceutical and chemical research. This heterocyclic compound features a pyrazole core substituted with chloro, chloromethyl, and methyl groups, making it a versatile intermediate for various synthetic applications. The unique structural attributes of this molecule contribute to its utility in the development of bioactive molecules, particularly in medicinal chemistry.

The pyrazole scaffold is well-documented for its broad spectrum of biological activities, including antimicrobial, anti-inflammatory, and anticancer properties. The presence of the chloro and chloromethyl substituents in 5-chloro-3-(chloromethyl)-1-methyl-1H-pyrazole enhances its reactivity, enabling further functionalization through nucleophilic substitution reactions. This characteristic makes it a valuable building block for designing novel therapeutic agents.

In recent years, there has been growing interest in the synthesis and application of pyrazole derivatives due to their potential pharmacological effects. Studies have demonstrated that compounds incorporating the pyrazole ring can modulate various biological pathways, making them attractive candidates for drug discovery. The 5-chloro-3-(chloromethyl)-1-methyl-1H-pyrazole structure provides a framework for exploring such interactions, particularly in the context of enzyme inhibition and receptor binding.

One of the most compelling aspects of 5-chloro-3-(chloromethyl)-1-methyl-1H-pyrazole is its role as a precursor in the synthesis of more complex molecules. Researchers have leveraged its reactive sites to develop derivatives with enhanced potency and selectivity. For instance, the chloromethyl group can be readily converted into other functional moieties such as alcohols or amines, facilitating the creation of diverse chemical libraries.

The pharmaceutical industry has been particularly keen on exploring pyrazole derivatives for their therapeutic potential. Preclinical studies have shown that certain modifications of the pyrazole core can lead to compounds with significant biological activity. The incorporation of electronegative atoms like chlorine enhances electronic properties, influencing both solubility and metabolic stability. These factors are critical in determining the pharmacokinetic profile of drug candidates.

Moreover, advances in computational chemistry have enabled more efficient virtual screening and design of pyrazole-based compounds. Molecular modeling techniques allow researchers to predict interactions between 5-chloro-3-(chloromethyl)-1-methyl-1H-pyrazole derivatives and biological targets with high precision. This approach accelerates the drug discovery process by identifying promising candidates before experimental validation.

The synthetic pathways for 5-chloro-3-(chloromethyl)-1-methyl-1H-pyrazole have also seen considerable innovation. Modern synthetic methods focus on improving yield, purity, and scalability while minimizing environmental impact. Catalytic processes and green chemistry principles are increasingly being applied to develop sustainable routes for producing this compound.

In conclusion, 5-chloro-3-(chloromethyl)-1-methyl-1H-pyrazole (CAS No. 524740-33-8) represents a crucial intermediate in pharmaceutical chemistry. Its structural features and reactivity make it an indispensable tool for designing novel bioactive molecules. As research continues to uncover new applications for pyrazole derivatives, compounds like this are poised to play a pivotal role in the development of next-generation therapeutics.

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