76205-20-4

Upstream product

• 76205-19-1 1-(para-chlorophenyl)-3-hydroxypyrazole 
• 6119-12-6 1-(4-chlorophenyl)-3-pyrazolidinone 
• 1073-70-7 4-chlorophenylhydrazine hydrochloride 
• 1073-69-4 N-4-chlorophenylhydrazine 

Relevant academic research and scientific papers

Synthesis and fungicidal activity of novel chloro-containing 1-Aryl-3-oxypyrazoles with an oximino ester or oximino amide moiety

Six novel chloro-containing 1-aryl-3-oxypyrazoles TMa-TMf with an oximino ester or an oximino amide moiety were prepared by the reaction of 1-aryl-1H-pyrazol-3-ols with benzyl bromide. Their structures were characterized by 1H-NMR, 13C-NMR, IR, MS, and elemental analysis. A preliminary in vitro bioassay indicated that compounds TMa, TMe and TMf displayed excellent fungicidal activity against Rhizoctonia solani and could be used as potential lead compounds for further development of novel fungicides.

DMF-catalyzed direct and regioselective C-H functionalization: Electrophilic/nucleophilic 4-halogenation of 3-oxypyrazoles

A novel, straightforward, and highly regioselective 4-chlorination of 3-oxypyrazole derivatives in boiling thionyl chloride (SOCl2) in the presence of catalytic N,N-dimethylformamide (DMF) has been developed. This reaction likely proceeds through a DMF-catalyzed electrophilic/nucleophilic chlorination mechanism and involves electrophilic attack by SOCl2 and nucleophilic substitution by Cl- as the key steps. Based on this mechanism, the corresponding 4-bromination and 4-iodination of 3-oxypyrazoles have also been achieved in good yield by adding Br- and I -, respectively, to the reaction system. This halogenation method enables quick access to many original 4-halo-3-oxypyrazole series. A novel DMF-catalyzed electrophilic/nucleophilic 4-halogenation of 3-oxypyrazole derivatives has been developed. This halogenation procedure provides quick access to many novel 4-halo-3-oxypyrazole series.