13618-35-4

Usage

Chemical class

Pyrazole derivatives

Molecular weight

172.228 g/mol

Usage

Organic synthesis and pharmaceutical research (building block for the synthesis of biologically active compounds)

Chemical structure

Pyrazole ring with two methyl groups at positions 3 and 4, and a phenyl group at position 5

Potential applications

Medicinal chemistry and drug discovery (due to pharmacological properties)

Upstream product

• 98-88-4 benzoyl chloride 
• 78-94-4 methyl vinyl ketone 
• 4812-23-1 2-nitro-but-2-ene 
• 1666-17-7 benzaldehyde p-toluenesulfonylhydrazone 
• 42968-14-9 (E)-3-methyl-4-phenyl-3-buten-2-one 
• 6668-24-2 2-methyl-1-phenyl-1,3-butanedione 

Downstream Products

• 59843-48-0 2-(4,5-dimethyl-3-phenyl-pyrazol-1-yl)-N,N-dimethyl-propionamide 
• 1335210-49-5 C₂₅H₂₀N₂ 
• 131339-05-4 (4,5-dimethyl-3-phenyl-1H-pyrazol-1-yl)(phenyl)methanone 
• 143950-74-7 1-acetyl-4,5-dimethyl-3-phenyl-1H-pyrazole 
• 131339-06-5 1-benzoyl-4,5-bis(bromomethyl)-3-phenyl-1H-pyrazole 
• 143950-62-3 1-acetyl-4,5-bis(bromomethyl)-3-phenyl-1H-pyrazole 
• 143950-68-9 2'-benzoyl-3,3-bis(2,6-dichlorophenyl)-5'-phenyl-isoxazole-5(4H)-spiro-3'(2'H)-pyrazole-4'-spiro-5(4H)-isoxazole 
• 143950-65-6 syn 2'-acetyl-3,3-bis(2,4,6-trimethylphenyl)-5'-phenyl-isoxazole-5(4H)-spiro-3'(2'H)-pyrazole-4'-spiro-5(4H)-isoxazole 
• 131339-07-6 1-benzoyl-4,5-dihydro-4,5-dimethylene-3-phenyl-1H-pyrazole 
• 131339-16-7 1-(1-Benzoyl-3-phenyl-4,5,6,7-tetrahydro-1H-indazol-5-yl)-ethanone 
• 131339-15-6 1-Benzoyl-3-phenyl-4,5,6,7-tetrahydro-1H-indazole-5-carbonitrile 
• 131339-13-4 1-(1-Benzoyl-3-phenyl-4,5,6,7-tetrahydro-1H-indazol-6-yl)-ethanone 
• 131339-12-3 1-Benzoyl-3-phenyl-4,5,6,7-tetrahydro-1H-indazole-6-carbonitrile 
• 131339-17-8 methyl 1-benzoyl-4,5,6,7-tetrahydro-3-phenyl-1H-indazole-56-carboxylate 

Relevant academic research and scientific papers

DABCO-promoted synthesis of pyrazoles from tosylhydrazones and nitroalkenes

An efficient synthesis of pyrazoles from tosylhydrazones and nitroalkenes was developed. In comparison with the previously reported 1,3-dipolar cycloaddition reaction of diazo compounds with electron-deficient alkenes or alkynes, this methodology proceeded with a sequential Baylis-Hillman/ intramolecular cyclization mechanism and a variety of reversed regioselectivity products were prepared in good yields.

Efficient one-pot synthesis of substituted pyrazoles

An efficient, one-pot synthesis of substituted pyrazoles from enones, hydrazides, and halides was developed. In comparison with the classical Knorr pyrazole synthesis, this methodology gave a different type of product (R 3≥R5). A range of substituted pyrazoles were prepared in good to high yields with complete regioselectivity.

Direct synthesis of 1,3-diketones by Rh-catalyzed reductive α-acylation of enones

(Chemical Equation Presented) 1,3-Diketones were synthesized from α,β-unsaturated ketones by treatment with acid chlorides and Et 2Zn in the presence of RhCl(PPh3)3. This is a very simple and extremely chemoselective reaction to give the adduct at the α-position of α,β-unsaturated ketones.

The Application of Microreactor Technology for the Synthesis of 1,2-Azoles

We demonstrate the successful synthesis of an array of 1,2-azoles within a borosilicate glass microreactor whereby conversions in the range of 98-100% were obtained. In terms of large-scale production, this corresponds to 0.339 g day-1 per microreactor when employing reagent concentrations of 1.0 M.