6963-62-8

Usage

Uses

Used in Pharmaceutical Industry:
1H-Pyrazole-3-carboxylic acid, 4-phenyl-, ethyl ester is used as a building block for the synthesis of various pharmaceutical compounds. Its unique structure allows for the creation of new drugs with potential therapeutic applications.
Used in Chemical Research:
1H-Pyrazole-3-carboxylic acid, 4-phenyl-, ethyl ester is used as a research compound in the field of organic chemistry. It serves as a model for studying the properties and reactions of pyrazole derivatives, contributing to the understanding of their chemical behavior and potential applications.
Used in Material Science:
1H-Pyrazole-3-carboxylic acid, 4-phenyl-, ethyl ester is used as a component in the development of new materials with specific properties. Its incorporation into polymers or other materials can lead to the creation of materials with unique characteristics, such as improved stability or enhanced reactivity.

InChI:InChI=1/C12H12N2O2/c1-2-16-12(15)11-10(8-13-14-11)9-6-4-3-5-7-9/h3-8H,2H2,1H3,(H,13,14)

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 102-96-5 (2-nitroethenyl)benzene 
• 14802-30-3 (E)-1-(4-methylphenyl)-3-phenyl-2-propen-1-one 
• 72758-71-5 3c-phenyl-1-p-tolyl-propenone 
• 187158-58-3 5-(4-Methyl-benzoyl)-4-phenyl-3,4-dihydro-2H-pyrazole-3-carboxylic acid ethyl ester 
• 5292-53-5 diethyl benzalmalonate 
• 2725-60-2 1-(p-methylphenylsulfonyl)-1-diazopropan-2-one 
• 620-80-4 ethyl 2-benzylidene acetoacetate 
• 98-86-2 acetophenone 
• 27262-63-1 ethyl 2-diazo-3-hydroxy-3-phenylbutanoate 
• 126580-13-0 ethyl 2-diazo-3-phenyl-3-butenoate 

Downstream Products

• 142598-53-6 2-methyl-4-phenyl-2H-pyrazole-3-carboxylic acid 
• 94033-65-5 4-phenyl-1⁽²⁾H-pyrazole-3-carboxylic acid hydrazide 
• 7510-56-7 4-phenyl-1H-pyrazole-3-carboxylic acid 
• 10199-68-5 4-phenyl-1H-pyrazole 
• 142598-52-5 ethyl 1-methyl-4-phenyl-1H-pyrazole-5-carboxylate 

Relevant academic research and scientific papers

1,3-Dipolar cycloaddition of chalcones and arylidene-1,3-dicarbonyls with diazosulfone for the regioselective synthesis of functionalized pyrazoles and pyrazolines

A convenient method for the synthesis of 3-acylpyrazoles and pyrazole-3-carboxylates using diazosulfone as a reactive 1,3-dipole and a diazomethane equivalent is reported here. Chalcones, arylidenemalonates and other arylidene-1,3-dicarbonyls performed we

Highly regioselective organocatalyzed synthesis of pyrazoles from diazoacetates and carbonyl compounds

A general, organocatalytic inverse-electron-demand [3+2] cycloaddition reaction between a range of carbonyl compounds and diazoacetates has been developed. This reaction is catalyzed by secondary amines as a "green promoter" to generate substituted pyrazoles with high levels of regioselectivity. It is noteworthy that this [3+2] cycloaddition reaction proceeds efficiently at room temperature with a simple and inexpensive catalyst. Considering the large variety and ready availability of the starting materials (e.g. ketones, β-ketoesters, β-diketones, and aldehydes), as well as the operational simplicity of this process, a convenient, practical, and highly modular pyrazole synthesis has been developed. We believe that this work will arouse more research interest in the organocatalytic synthesis of other biologically active heterocycles. Such studies are currently underway in our laboratory. Dipoles apart: In situ formed enamines react with diazoacetates under mild conditions to afford the corresponding polysubstituted pyrazoles in good-to-excellent yields through an inverse-electron-demand 1,3-dipolar cycloaddition process (see scheme). Copyright

Efficient method for the synthesis of functionalized pyrazoles by catalyst-free one-pot tandem reaction of nitroalkenes with ethyl diazoacetate

The one-pot synthesis of multisubstituted pyrazole derivatives was achieved via catalyst-free 1,3-dipolar cycloaddition of ethyl diazoacetate and nitroalkenes as the key step and elimination of the leaving group (NO 2 or Br) followed by intramo

Synthesis and reactions of some ethyl 3-aroyl-4-aryl-2-pyrazoline-5-carboxylates

A series of ethyl 3-aroyl-4-aryl-2-pyrazoline-5-carboxylates 1 was prepared. Their reactions with bromine water, potassium permanganate and potassium hydroxide afforded the corresponding pyrazoles. With aryl and aroyl hydrazines the pyrazolines 1 gave the Schiff bases 9 while with hydrazine hydrate they yielded the corresponding acid hydrazides 11. Condensation of 11 with aromatic aldehydes gave the arylidene derivatives 12, which on cyclization with the proper reagent afforded 13 or 14. Reaction of 1 with hydrochloric acid gave the corresponding dipyrazolo-pyrazine derivatives 10.

Synthesis and reactions of some ethyl 3(5)aroyl-4-aryl-2-pyrazoline-5(3)carboxylates

A series of ethyl 3(5)aroyl-4-aiyl-2-pyrazoline-5(3)carboxylates 1 was prepared. Their reactions with bromine water, potassium permanganate and potassium hydroxide afforded the corresponding pyrazoles. With aryl and aroyl hydrazines the pyrazolines 1 gave the Schiff bases 9 while with hydrazine hydrate they yielded the corresponding acid hydrazides 11. Condensation of 11 with aromatic aldehydes gave the arylidene derivatives 12, which, on cyclization with the propar reagent, afforded 13 or 14. Reaction of 1 with hydrochloric acid gave the corresponding dipyrazolo-pyrazine derivatives 10.

Reaction of Carbonyl Compounds with Ethyl Lithiodiazoacetate. Studies Dealing with the Rhodium(II)-Catalyzed Behavior of the Resulting Adducts

The carbenoid intermediate derived by treating ethyl 2-diazo-4-phthalimidobutyrate with rhodium(II) octanoate undergoes transannular cyclization onto the adjacent imido carbonyl group.The resulting cyclic carbonyl ylide diploe was trapped with several dipolarophiles.In an attempt to prepare related substrates for cyclization studies, the reaction of ethyl lithiodiazoacetate with various aldehydes and ketones was studied.Treatment of the α-diazo-β-hydroxy ester derived from acetone or cyclopentanone with rhodium(II) octanoate gave rise to a β-keto ester.The exclusive phenyl shift encountered with acetophenone is in keeping with migration to an electron-deficient center.The reaction works well with acrolein, leading to high yields of 3-oxo-4-pentenoate.The 1,2-hydrogen shift pathway was found to proceed much faster than intramolecular cyclopropanation.Dehydration of the α-diazo-β-hydroxy esters generates vinyl diazo esters, which readily cyclize to 1H-pyrazoles on thermolysis.