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

Uses

3-Difluoromethyl-1-methylpyrazole-4-carboxylic Acid Ethyl Ester is useful synthetic intermediate. It can be used to prepare 3-difluoromethylpyrazolecarboxamide fungicides.

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

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• 60-34-4 methylhydrazine 
• 50-00-0 formaldehyd 
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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.

Expanding the Chemical Space of Succinate Dehydrogenase Inhibitors via the Carbon-Silicon Switch Strategy

The carbon-silicon switch strategy has become a key technique for structural optimization of drugs to widen the chemical space, increase drug activity against targeted proteins, and generate novel and patentable lead compounds. Flubeneteram, targeting succinate dehydrogenase (SDH), is a promising fungicide candidate recently developed in China. We describe the synthesis of novel SDH inhibitors with enhanced fungicidal activity to enlarge the chemical space of flubeneteram by employing the C-Si switch strategy. Several of the thus formed flubeneteram-silyl derivatives exhibited improved fungicidal activity against porcine SDH compared with the lead compound flubeneteram and the positive controls. Disease control experiments conducted in a greenhouse showed that trimethyl-silyl-substituted compound W2 showed comparable and even higher fungicidal activities compared to benzovindiflupyr and flubeneteram, respectively, even with a low concentration of 0.19 mg/L for soybean rust control. Furthermore, compound W2 encouragingly performed slightly better control than azoxystrobin and was less active than benzovindiflupyr at the concentration of 100 mg/L against soybean rust in field trials. The computational results showed that the silyl-substituted phenyl moiety in W2 could form strong van der Waals (VDW) interactions with SDH. Our results indicate that the C-Si switch strategy is an effective method for the development of novel SDH inhibitors.

Preparation method of 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester

The invention discloses a preparation method of 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester, and belongs to the technical field of organic synthesis. The preparation method comprises the following steps: with 1,3-dimethylpyrazole as a raw material, carrying out halogenation to obtain 4-halogenated-1,3,5-tetrahydronaphthalene; carrying out a reaction under the conditions of a bromination reagent and AIBN and hydrolysis with hexamethylenetetramine to obtain 4-halogen-1-methyl-1H-pyrazole-3-formaldehyde, then performing a reaction with a fluorination reagent to obtain 4-halogen-3-difluoromethyl-1-methylpyrazole; finally carrying out a reaction on the 4-halogen-3-difluoromethyl-1-methylpyrazole and a Grignard reagent to obtain 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester. The method is simple and convenient to operate and high in reaction yield, the purity of the obtained product can reach 99.5% or above, and the method has a potential process amplification prospect.