141573-95-7

Basic information

• Product Name: Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate
• Synonyms: Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate;3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester;1H-Pyrazole-4-carboxylic acid, 3-(difluoroMethyl)-1-Methyl-, ethyl ester;Ethyl-3-difluoromethyl-1-methyl-1H-pyraz.
• CAS NO: 141573-95-7
• Molecular Formula: C₈H₁₀F₂N₂O₂
• Molecular Weight: 204.175
• Product Categories: Building Blocks;Pyrazole
• Mol File: 141573-95-7.mol
• Article Data: 70

Chemical Properties

• Melting Point: 58-59 °C
• Boiling Point: 288.448 °C at 760 mmHg
• Flash Point: 128.249 °C
• Appearance: /
• Density: 1.307 g/cm³
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.494
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: -2.00±0.10(Predicted)
• Water Solubility: 4.63g/L at 22℃
• CAS DataBase Reference: Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate(141573-95-7)
• EPA Substance Registry System: Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate(141573-95-7)

Safety Data

• Hazardous Substances Data: 141573-95-7(Hazardous Substances Data)

Usage

Description

Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate is an organic compound that serves as a crucial synthetic intermediate in the chemical industry. It is characterized by its unique molecular structure, which includes a difluoromethyl group, a methyl group, and a pyrazole ring, all attached to an ester functional group. Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate is known for its potential applications in various fields due to its versatile chemical properties.

Uses

Used in Pharmaceutical Industry:
Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate is used as a synthetic intermediate for the development of various pharmaceutical compounds. Its unique structure allows for the creation of new molecules with potential therapeutic applications, contributing to the advancement of drug discovery and development.
Used in Agrochemical Industry:
Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate is used as a key intermediate in the synthesis of 3-difluoromethylpyrazole-carboxamide fungicides. These fungicides are designed to protect crops from fungal infections, ensuring higher yields and better quality produce. The compound's role in the development of these fungicides highlights its importance in the agrochemical industry.

InChI:InChI=1/C8H10F2N2O2/c1-3-14-8(13)5-4-12(2)11-6(5)7(9)10/h4,7H,3H2,1-2H3

Upstream product

• 60-34-4 methylhydrazine 
• 851725-87-6 ethyl 3-(dichloromethyl)-1-methyl-1H-pyrazole-4-carboxylate 
• 1086400-66-9 (Z)-2-(ethoxymethylene)-4,4-difluoro-3-oxobutanoic acid ethyl ester 
• 176969-33-8 (E/Z)-ethyl 2-(ethoxymethylene)-4,4-difluoro-3-oxobutanoate 
• 512-56-1 trimethyl phosphite 
• 151733-96-9 ethyl 3-(difluoromethyl)-1H-pyrazole-4-carboxylate 
• 64-17-5 ethanol 
• 1089212-38-3 4-bromo-3-(difluoromethyl)-1-methyl-1H-pyrazole 
• 201230-82-2 carbon monoxide 
• 72153-33-4 1-methyl-2-dfluoroacetylhydrazine 
• 623-47-2 propynoic acid ethyl ester 
• 1094495-17-6 4,4-difluoro-2-[1-methylamino-meth-(E)-ylidene]-3-oxo-butyric acid ethyl ester 
• 1009318-76-6 N-[(2E)-1-(difluoromethyl)-3-(dimethylamino)-2-(ethoxycarbonyl)prop-2-en-1-ylidene]-N-methylmethanaminium tetrafluoroborate 
• 571-55-1 ethyl 2-(ethoxymethylidene)-4,4,4-trifluoro-3-oxobutanoate 

Downstream Products

• 176969-34-9 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid 
• 956481-28-0 3-(difluoromethyl)-1-methyl-N-(2-biphenyl)-4-pyrazole carboxamide 
• 1373886-87-3 C₁₃H₁₂F₃N₃O 
• 1373886-86-2 C₁₂H₁₀F₃N₃O 
• 1373886-88-4 C₁₂H₈Cl₃F₂N₃O 
• 581809-46-3 bixafen 
• 874967-67-6 sedaxane 
• 881685-58-1 isopyrazam 
• 141573-96-8 3‐difluoromethyl‐1‐methylpyrazole-4-carbonyl chloride 

Relevant articles and documents

Crystal structure and molecular docking studies of new pyrazole-4-carboxamides

Two pyrazol-4-carboxamides, 3-(difluoromethyl)-N-(mesitylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxa-mide (7a) and 3-(difluoromethyl)-N-((3,5-dimethylphenyl) carbamoyl)-1-methyl-1H-pyrazole-4-carboxamide (7b) were synthesized and their structures were confirmed by the aid of 1H NMR and HRMS analyses. The structure of the pyrazole-4-carboxamide, 7a was also determined by X-ray diffraction. The preliminary activity results demonstrate that these two compounds exhibit good inhibitory activity against Botrytis cinerea. Further docking results indicated that the key active group is difluoromethyl pyrazole moiety.

Synthesis, nematocidal activity and SAR study of novel difluoromethylpyrazole carboxamide derivatives containing flexible alkyl chain moieties

A series of novel difluoromethylpyrazole carboxamides derivatives were synthesized by introduction of flexible alkyl chain. Nematicidal bioassay results showed that some of them exhibited good control efficacy against M. incognita, which indicated that these difluoromethylpyrazole carboxamides derivatives might be potential novel lead compounds for discovery new nematicides. The nematicidal activity was affected by the substituted position in the molecule, especially the substitution group on the alkyl chain. It was found that the compound 6-9 and 6-23 possess about 50% inhibition effect against M. incognita even at 5.0 and 1.0 mg L?1. Meanwhile, greenhouse field trial showed the nematicidal activity of compound 6-9 is a litter weaker than that of Abamectin. The mammalian toxicology results indicated that compound 6-9 was a low-toxicity and low-sensitive compound. In conclusion compound 6-9 is a potential candidate for further development. In addition, the molecular docking simulations revealed that compounds 6 with a flexible NHCOO show its binding affinities for the acetylcholine receptor (AChR), which may provide useful information for further design novel nematicides.

Synthesis, Crystal Structure, Antifungal Activity, and Docking Study of Difluoromethyl Pyrazole Derivatives

Nine novel difluoromethylpyrazole acyl urea derivatives were synthesized via seven steps conveniently. All the structures were determined by 1H-NMR, 13C-NMR, HRMS, and X-ray diffraction. The in vivo fungicidal activities were determined against Corynespora mazei, Botrytis cinerea, Fusarium oxysporum, and Pseudomonas syringae, respectively. The bioassay results indicated that some of them displayed good control effective (around 50 and 80%) against P. syringae and B. cinerea at 50 mg/L, respectively, which is better than control. It is possible that difluoromethylpyrazole acyl urea derivatives can be a leading compound for the development of new fungicides against the two fungi with further structure optimization. Furthermore, docking model was studied to establish structure–activity relationship of difluoromethylpyrazole acyl urea derivatives.

Synthesis and preparation method of 4-pyrazole ethyl formate

The invention discloses a synthesis and preparation method of 4-pyrazole ethyl formate. The method comprises the following steps: dissolving ethyl 2-dichloroacetyl-3-(dimethylamino) acrylate in an organic solvent, and reacting with methylhydrazine to obtain ethyl 1-methyl-3-dichloromethyl-4-pyrazole formate; reacting the obtained ethyl 1-methyl-3-dichloromethyl-4-pyrazole formate with a fluorination reagent to obtain 1-methyl- 3-difluoromethyl-4-pyrazole ethyl formate; mixing 1-methyl- 3-difluoromethyl-4-pyrazole ethyl formate with glacial acetic acid, dropwise adding a strong acidic solutionat the temperature of 0 DEG C, and then adding dichloromethane and water for stirring and layering to obtain an organic layer; and recrystallizing the organic layer by using a mixed solvent of petroleum ether and ethyl acetate to obtain the 4-pyrazole ethyl formate. The method has the advantages of wide raw material source, low raw material price and simple preparation process, and the obtained product is easy to purify, low in production cost and suitable for large-scale industrial production.

Expedient discovery for novel antifungal leads targeting succinate dehydrogenase: Pyrazole-4-formylhydrazide derivatives bearing a diphenyl ether fragment

The pyrazole-4-carboxamide scaffold containing a flexible amide chain has emerged as the molecular skeleton of highly efficient agricultural fungicides targeting succinate dehydrogenase (SDH). Based on the above vital structural features of succinate dehydrogenase inhibitors (SDHI), three types of novel pyrazole-4-formylhydrazine derivatives bearing a diphenyl ether moiety were rationally conceived under the guidance of a virtual docking comparison between bioactive molecules and SDH. Consistent with the virtual verification results of a molecular docking comparison, the in vitro antifungal bioassays indicated that the skeleton structure of title compounds should be optimized as an N′-(4-phenoxyphenyl)-1H-pyrazole-4-carbohydrazide scaffold. Strikingly, N′-(4-phenoxyphenyl)-1H-pyrazole-4-carbohydrazide derivatives 11o against Rhizoctonia solani, 11m against Fusarium graminearum, and 11g against Botrytis cinerea exhibited excellent antifungal effects, with corresponding EC50 values of 0.14, 0.27, and 0.52 μg/mL, which were obviously better than carbendazim against R. solani (0.34 μg/mL) and F. graminearum (0.57 μg/mL) as well as penthiopyrad against B. cinerea (0.83 μg/mL). The relative studies on an in vivo bioassay against R. solani, bioactive evaluation against SDH, and molecular docking were further explored to ascertain the practical value of compound 11o as a potential fungicide targeting SDH. The present work provided a non-negligible complement for the structural optimization of antifungal leads targeting SDH.