110821-33-5

Basic information

• Product Name: ethyl 1-(4-chlorophenyl)-1H-pyrazole-4-carboxylate
• Synonyms: ethyl 1-(4-chlorophenyl)-1H-pyrazole-4-carboxylate;1-(4-Chlorophenyl)-1H-pyrazole-4-carboxylic acid ethyl ester
• CAS NO: 110821-33-5
• Molecular Formula: C₁₂H₁₁ClN₂O₂
• Molecular Weight: 250.68094
• Mol File: 110821-33-5.mol

Chemical Properties

• Melting Point: 127-129℃ (ethanol )
• Appearance: /
• CAS DataBase Reference: ethyl 1-(4-chlorophenyl)-1H-pyrazole-4-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 1-(4-chlorophenyl)-1H-pyrazole-4-carboxylate(110821-33-5)
• EPA Substance Registry System: ethyl 1-(4-chlorophenyl)-1H-pyrazole-4-carboxylate(110821-33-5)

Safety Data

• Hazardous Substances Data: 110821-33-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 1-(4-chlorophenyl)-1H-pyrazole-4-carboxylate is used as a research compound for exploring its potential therapeutic applications. Its unique structure may contribute to the development of new drugs targeting various diseases and conditions.
Used in Agrochemical Industry:
In the agrochemical sector, ethyl 1-(4-chlorophenyl)-1H-pyrazole-4-carboxylate is utilized as a building block in the synthesis of novel agrochemicals. Its chemical properties may enable the creation of innovative products for crop protection and pest management.
Used in Chemical Synthesis:
Ethyl 1-(4-chlorophenyl)-1H-pyrazole-4-carboxylate serves as a key intermediate in the synthesis of other organic compounds. Its unique structure allows for the development of new chemical entities with potential applications in various industries.
Used in Research and Development:
ethyl 1-(4-chlorophenyl)-1H-pyrazole-4-carboxylate is employed as a research tool in laboratories to study its chemical properties, reactivity, and potential interactions with other molecules. Understanding its behavior can lead to the discovery of new applications and uses in different fields.

Upstream product

• 225930-54-1 3-amino-1-(4-chloro-phenyl)-1H-pyrazole-4-carboxylic acid ethyl ester 
• 1073-69-4 N-4-chlorophenylhydrazine 
• 623-73-4 diazoacetic acid ethyl ester 
• 75119-97-0 glyoxal 4-chlorophenylhydrazone 
• 4830-74-4 (4-chlorophenyl)azo 4-methylphenyl sulfone 
• 37622-90-5 4-ethoxycarbonylpyrazole 
• 352-33-0 1-Chloro-4-fluorobenzene 
• 637-87-6 1-Chloro-4-iodobenzene 
• 1073-70-7 4-chlorophenylhydrazine hydrochloride 
• 144918-37-6 (E)-ethyl 2-cyano-3-ethoxyacrylate 
• 94-05-3 ethyl (ethoxymethylene)cyanoacetate 
• 14678-87-6 ethyl 5-amino-1-(4-chlorophenyl)-1H-pyrazole-4-carboxylate 
• 80370-42-9 ethyl 2-formyl-3-oxopropanoate 
• 108-90-7 chlorobenzene 

Downstream Products

• 138907-80-9 1-(4-chlorophenyl)-1H-pyrazole-4-carboxylic acid 

Relevant articles and documents

Process research, development, and pilot-plant preparation of clofencet, a novel wheat hybridizing agent: Lewis acid-catalyzed reaction of ethyl diazoacetate with 4-chlorophenyl hydrazonoacetaldehyde

Described are studies directed toward the chemical research and development of an alternative synthesis to 9, the penultimate intermediate of clofencet (1), a novel wheat-hybridizing agent. Retrosynthetic analyses as well as the results obtained from feasibility studies are detailed, leading to the successful development of an alternative process. The key features of the novel route are a method for preparing on-scale ethyl diazoacetate (28) in a safe and effective manner, and the Lewis acid-catalyzed reaction of 28 with hydrazonoacetaldehyde 29, affording β-ketoester 30. The synthesis is completed via propionylation of 30, acid-catalyzed cyclization of 31 to pyridazinecarboxylic acid ester 32, followed by saponification and isolation of carboxylic acid 9. The results and challenges of eight pilot-plant runs are reported. The baseline process developed produced over 45 kg of 9 in 43-45% yield.

Synthesis of pyrazole-carboxamides and pyrazole-carboxylic acids derivatives: Simple methods to access powerful building blocks

Hybrid systems containing pyrazole moiety show a wide spectrum of biological activities. To access novel hybrids with pyrazole ring, in this work we synthesized twenty pyrazole-carboxylic acids and twenty pyrazole-carboxamides, using simple synthetic methods, to be used as building blocks in the development of new structures.

Unveiling Potent Photooxidation Behavior of Catalytic Photoreductants

We describe a photocatalytic system that reveals latent photooxidant behavior from one of the most reducing conventional photoredox catalysts, N-phenylphenothiazine (PTH). This aerobic photochemical reaction engages difficult to oxidize feedstocks, such as benzene, in C(sp2)-N coupling reactions through direct oxidation. Mechanistic studies are consistent with activation of PTH via photooxidation and with Lewis acid cocatalysts scavenging inhibitors inextricably formed in this process.

Design, synthesis, biological evaluation and in silico studies of pyrazole‐based nh2‐acyl oseltamivir analogues as potent neuraminidase inhibitors

Oseltamivir represents one of the most successful neuraminidase (NA) inhibitors in the current anti‐influenza therapy. The 150‐cavity of NA was identified as an additional binding pocket, and novel NA inhibitors have been designed to occupy the 150‐cavity

Electrophotocatalytic SNAr Reactions of Unactivated Aryl Fluorides at Ambient Temperature and Without Base

The electrophotocatalytic SNAr reaction of unactivated aryl fluorides at ambient temperature without strong base is demonstrated.

Organophotochemical SNAr Reactions of Mildly Electron-Poor Fluoroarenes

C–F functionalization of arenes with a range of alcohol and pyrazole nucleophiles has been achieved without the need for metal catalysts or highly electron-poor substrates. Treatment of fluoroarenes with alcohols or pyrazoles and DDQ under irradiation by blue LED light provides the corresponding substituted products. The procedure is complementary to classical SNAr chemistry which generally requires basic reaction conditions and high temperatures, and provides products under non-basic conditions at ≈ 40 °C.

Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication

Visible-light photocatalysis and electrocatalysis are two powerful strategies for the promotion of chemical reactions. Here, these two modalities are combined in an electrophotocatalytic oxidation platform. This chemistry employs a trisaminocyclopropenium (TAC) ion catalyst, which is electrochemically oxidized to form a cyclopropenium radical dication intermediate. The radical dication undergoes photoexcitation with visible light to produce an excited-state species with oxidizing power (3.33 V vs. SCE) sufficient to oxidize benzene and halogenated benzenes via single-electron transfer (SET), resulting in C?H/N?H coupling with azoles. A rationale for the strongly oxidizing behavior of the photoexcited species is provided, while the stability of the catalyst is rationalized by a particular conformation of the cis-2,6-dimethylpiperidine moieties.

nBu3P-catalyzed desulfonylative [3 + 2] cycloadditions of allylic carbonates with arylazosulfones to pyrazole derivatives

Highly efficient nBu3P-catalyzed desulfonylative [3 + 2] cycloadditions of allylic carbonates with arylazosulfones were developed for the synthesis of pyrazole derivatives. The reactions proceed smoothly under mild conditions to gene

Synthesis and structure - Activity relationships of 1-phenylpyrazoles as xanthine oxidase inhibitors

A series of 1-phenylpyrazoles was evaluated for inhibitory activity against xanthine oxidase in vitro. Of the compounds prepared, 1-(3-cyano-4-neopentyloxyphenyl)pyrazole-4-carboxylic acid (Y-700) had the most potent enzyme inhibition and displayed longer-lasting hypouricemic action than did allopurinol in a rat model of hyperuricemia induced by the uricase inhibitor potassium oxonate.

N-1 Substituted Ethyl 4-Pyrazolecarboxylates: Synthesis and Spectroscopic Investigations

The synthesis of various N-1 substituted ethyl 4-pyrazolecarboxylates via reaction of ethyl 2-formyl-3-oxopropionate (= ethoxycarbonylmalondialdehyde) with appropriately substituted hydrazines is described.Moreover, detailed nmr-spectroscopic investigations with the title compounds are presented.