176969-34-9

Basic information

• Product Name: 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid
• Synonyms: 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid;3-Difluoromethyl-1-methyl-1H-pyrazol-4-carboxylic acid;3-Difluoromethyl-1-methylpyrazole-4-carboxylic acid;1H-Pyrazole-4-carboxylicacid, 3-(difluoroMethyl)-1-Methyl-;3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxyl
• CAS NO: 176969-34-9
• Molecular Formula: C₆H₆F₂N₂O₂
• Molecular Weight: 176.121
• Product Categories: Building Blocks;Pyrazole
• Mol File: 176969-34-9.mol

Chemical Properties

• Boiling Point: 315.9 °C at 760 mmHg
• Flash Point: 144.851 °C
• Appearance: /
• Density: 1.52
• Vapor Pressure: 0.000179mmHg at 25°C
• Refractive Index: 1.533
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Sparingly)
• PKA: 3.12±0.36(Predicted)
• CAS DataBase Reference: 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid(176969-34-9)
• EPA Substance Registry System: 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid(176969-34-9)

Safety Data

• Hazardous Substances Data: 176969-34-9(Hazardous Substances Data)

Usage

Uses

Used in Pesticide Industry:
3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid is used as an active ingredient for the preparation of pesticides. Its chemical structure suggests that it may possess properties effective in controlling pests, particularly in agricultural settings. The difluoromethyl group might enhance its pesticidal activity by potentially increasing its lipophilicity and bioavailability to target pests, while the methyl group could influence its stability and metabolic profile in the environment.

InChI:InChI=1/C6H6F2N2O2/c1-10-2-3(6(11)12)4(9-10)5(7)8/h2,5H,1H3,(H,11,12)

Synthetic route

1-(3-(difluoromethyl)-1-methyl-1H-pyrazol-4-yl)ethan-1-one → 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9)

Conditions	Yield
With manganese(II) acetate dihydrate; acetic acid at 100℃; for 18h; Reagent/catalyst;	100%
With sodium hypochlorite; sodium hydroxide In water at 70℃; for 2h; Temperature; Reagent/catalyst;	98%
With sodium hypochlorite In water at 0℃; for 0.166667h; Temperature; Time;	98%

ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate (141573-95-7) → 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9)

Conditions	Yield
With sodium hydroxide In toluene at 65℃; for 0.75h;	98%
With sodium hydroxide In ethanol; water at 50 - 80℃; for 3h;	95%
With water; sodium hydroxide	95%

hexylene glycol bis((3-(difluoromethyl)-1-methyl-1H-pyrazol-4-yl)carboxylate) → 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9)

Conditions	Yield
With water; sodium hydroxide In methanol at 60℃; for 4h;	96.3%

3‐difluoromethyl‐1‐methylpyrazole-4-carbonyl chloride (141573-96-8) + C12H13Cl2NO (1263184-89-9) → 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9) + benzovindiflupyr

Conditions	Yield
Stage #1: 3‐difluoromethyl‐1‐methylpyrazole-4-carbonyl chloride; C12H13Cl2NO With triethylamine In 1,4-dioxane at 25 - 82℃; for 3h; Stage #2: With sodium hydroxide In tert-butyl methyl ether; water for 0.5h; Stage #3: With hydrogenchloride In tert-butyl methyl ether; water	A 96% B 92%

3-difluoromethyl-1-methyl-1H-pyrazole-4-carbonitrile (1049772-84-0) → 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9)

Conditions	Yield
With sodium hydroxide In water at 90 - 100℃;	95%
Stage #1: 3-difluoromethyl-1-methyl-1H-pyrazole-4-carbonitrile With water; sodium hydroxide at 95℃; for 4h; Stage #2: With hydrogenchloride; water at 20℃; Cooling with ice;	92%
With water; sodium hydroxide In methanol for 2h; Solvent; Reflux; Further stages;	92.1%
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In water; toluene at 70℃; for 8h;

hexyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate → 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9)

Conditions	Yield
With water; sodium hydroxide at 60℃; for 2h;	95%

methyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate → 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9)

Conditions	Yield
With manganese(II) nitrate; oxygen; acetic acid; ferric nitrate at 80℃; for 20h;	95%

3-(difluoromethyl)-1-methyl-4-(1,3-dioxolan-2-yl)-1H-pyrazole → 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9)

Conditions	Yield
Stage #1: 3-(difluoromethyl)-1-methyl-4-(1,3-dioxolan-2-yl)-1H-pyrazole With hydrogenchloride In water at 50 - 60℃; for 5h; Stage #2: With dihydrogen peroxide In water at 10 - 100℃; for 5h; Reagent/catalyst;	93.2%

3-(difluoromethyl)-1-methyl-4-(2-methyl-1,3-dioxan-2-yl)-1H-pyrazole → 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9)

Conditions	Yield
Stage #1: 3-(difluoromethyl)-1-methyl-4-(2-methyl-1,3-dioxan-2-yl)-1H-pyrazole With hydrogenchloride In water at 50 - 60℃; for 5h; Stage #2: With dihydrogen peroxide In water at 10 - 100℃; for 5h;	92.3%

ethylene glycol bis((3-(difluoromethyl)-1-methyl-1H-pyrazol-4-yl)carboxylate) → 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9)

Conditions	Yield
With water; sodium hydroxide In methanol at 60℃; for 4h; Reagent/catalyst;	92%

3-(difluoromethyl)-1-methyl-4-(2-methyl-1,3-dioxepan-2-yl)-1H-pyrazole → 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9)

Conditions	Yield
Stage #1: 3-(difluoromethyl)-1-methyl-4-(2-methyl-1,3-dioxepan-2-yl)-1H-pyrazole With hydrogenchloride In water at 50 - 60℃; for 5h; Stage #2: With dihydrogen peroxide In water at 10 - 100℃; for 5h;	92%

3-(difluoromethyl)-1-methyl-4-(2-methyl-1,3-dioxolan-2-yl)-1H-pyrazole → 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9)

Conditions	Yield
Stage #1: 3-(difluoromethyl)-1-methyl-4-(2-methyl-1,3-dioxolan-2-yl)-1H-pyrazole With hydrogenchloride In water at 50 - 60℃; for 5h; Stage #2: With sodium hypochlorite In water at 10 - 100℃; for 5h;	91.8%

3-(difluoromethyl)-4-(1,3-dioxan-2-yl)-1-methyl-1H-pyrazole → 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9)

Conditions	Yield
Stage #1: 3-(difluoromethyl)-4-(1,3-dioxan-2-yl)-1-methyl-1H-pyrazole With hydrogenchloride In water at 50 - 60℃; for 5h; Stage #2: With dihydrogen peroxide In water at 10 - 100℃; for 5h; Reagent/catalyst;	91.6%

3-(difluoromethyl)-1-methyl-4-(1,3-dioxepan-2-yl)-1H-pyrazole → 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9)

Conditions	Yield
Stage #1: 3-(difluoromethyl)-1-methyl-4-(1,3-dioxepan-2-yl)-1H-pyrazole With hydrogenchloride In water at 50 - 60℃; for 5h; Stage #2: With dihydrogen peroxide In water at 10 - 100℃; for 5h; Reagent/catalyst;	91.5%

3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde (1094484-55-5) → 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9)

Conditions	Yield
With sodium hypochlorite at 10 - 100℃; for 5h;	91.3%
Stage #1: 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde With sodium hydroxide; dihydrogen peroxide In water at 40 - 45℃; for 1.5h; Stage #2: With hydrogenchloride In water pH=2.5; Product distribution / selectivity;	69 %Chromat.
With copper(II) oxide; sodium hydroxide In water at 25 - 30℃; for 24h;	32 g

3-(difluoromethyl)-1-methyl-4-(2-methyl-1,3-dioxetan-2-yl)-1H-pyrazole → 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9)

Conditions	Yield
Stage #1: 3-(difluoromethyl)-1-methyl-4-(2-methyl-1,3-dioxetan-2-yl)-1H-pyrazole With hydrogenchloride In water at 50 - 60℃; for 5h; Stage #2: With sodium hypochlorite In water at 10 - 100℃; for 5h; Reagent/catalyst;	91.3%

2,2-dichloro-1-(3-(difluoromethyl)-1-methyl-1H-pyrazol-4-yl)ethanone → 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9)

Conditions	Yield
With sodium hypochlorite; water In chloroform at 24℃; for 4h; Reagent/catalyst; Inert atmosphere;	91%
With sodium hypochlorite; sodium hydroxide In water at 22 - 70℃; for 2h;

3-(difluoromethyl)-4-(1,3-dioxetan-2-yl)-1-methyl-1H-pyrazole → 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9)

Conditions	Yield
Stage #1: 3-(difluoromethyl)-4-(1,3-dioxetan-2-yl)-1-methyl-1H-pyrazole With hydrogenchloride In water at 50 - 60℃; for 5h; Stage #2: With sodium hypochlorite In water at 10 - 100℃; for 5h; Reagent/catalyst;	91%

methyl-3-(dichloromethyl)-1-methyl-1H-pyrazole-4-carboxylate → 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9) + 5-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (1204298-65-6)

Conditions	Yield
With 1,3-dimethyl-2-imidazolidinone; hydrogen fluoride; triethylamine at 125 - 155℃; Reagent/catalyst; Temperature; Concentration; Autoclave;	A 90.1% B n/a

3-(difluoromethyl)-4-(furan-2-yl)-1-methyl-1H-pyrazole → 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9)

Conditions	Yield
With sodium periodate; rhodium(III) chloride hydrate In tetrachloromethane; water; acetonitrile at 20℃; for 0.75h;	90%

3-bromo-1-methyl-1H-pyrazole-4-carboxylic acid + difluoromethylboronic acid → 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 65 - 75℃; for 1.5h; Solvent; Reagent/catalyst; Inert atmosphere;	89.2%

(E/Z)-ethyl 2-(ethoxymethylene)-4,4-difluoro-3-oxobutanoate + methylhydrazine (60-34-4) → 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9)

Conditions	Yield
Stage #1: methylhydrazine With benzaldehyde In water; toluene at 25 - 60℃; for 6.16667h; Inert atmosphere; Stage #2: (E/Z)-ethyl 2-(ethoxymethylene)-4,4-difluoro-3-oxobutanoate In water; toluene at 20 - 30℃; for 19h; Product distribution / selectivity;	86.1%

4-bromo-3-(difluoromethyl)-1-methyl-1H-pyrazole (1089212-38-3) + carbon dioxide (124-38-9) → 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9)

Conditions	Yield
Stage #1: 4-bromo-3-(difluoromethyl)-1-methyl-1H-pyrazole With TurboGrignard In 2-methyltetrahydrofuran at -5℃; for 2h; Inert atmosphere; Heating; Stage #2: carbon dioxide In 2-methyltetrahydrofuran at -25 - 0℃; for 5h; Reagent/catalyst; Solvent; Inert atmosphere;	84.6%

ethyl 4,4-difluoro-3-oxobutyrate (352-24-9) + methylhydrazine (60-34-4) → 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9)

Conditions	Yield
Stage #1: ethyl 4,4-difluoro-3-oxobutyrate With calcium acetate; orthoformic acid triethyl ester at 100 - 110℃; for 2h; Stage #2: methylhydrazine With sodium hydroxide In 5,5-dimethyl-1,3-cyclohexadiene; water at 10 - 20℃; for 0.5h;	83.3%

carbon dioxide (124-38-9) + 3-(difluoromethyl)-4-iodo-1-methyl-1H-pyrazole → 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9)

Conditions	Yield
Stage #1: 3-(difluoromethyl)-4-iodo-1-methyl-1H-pyrazole With isopropylmagnesium chloride In tetrahydrofuran at -5℃; for 2h; Inert atmosphere; Heating; Stage #2: carbon dioxide With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at -25 - 0℃; for 5h; Inert atmosphere;	83.2%

potassium 2-difluoroacetyl-3-(diethylamino)acrylate + methylhydrazine (60-34-4) → 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9)

Conditions	Yield
With potassium iodide In water at -30 - -20℃; for 2h; Inert atmosphere;	79.6%

sodium 2-difluoroacetyl-3-(dimethylamino)acrylate + methylhydrazine (60-34-4) → 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9)

Conditions	Yield
With sodium iodide In water at -30 - 20℃; for 2h; Inert atmosphere;	78.3%

sodium 2-difluoroacetyl-3-(diethylamino)acrylate + methylhydrazine (60-34-4) → 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9)

Conditions	Yield
With sodium iodide at -30 - -25℃; for 2h; Inert atmosphere;	77.1%

potassium 2-difluoroacetyl-3-(dimethylamino)acrylate → 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9)

Conditions	Yield
With methylhydrazine; potassium iodide In water at -30 - -20℃; for 2h; Inert atmosphere;	75.9%

sodium 2-difluoroacetyl-3-(2,2,6,6-tetramethylpiperidin-1yl)acrylate + methylhydrazine (60-34-4) → 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9)

Conditions	Yield
With sodium iodide at -30 - -20℃; for 2h; Inert atmosphere;	75.8%

3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9) → 3‐difluoromethyl‐1‐methylpyrazole-4-carbonyl chloride (141573-96-8)

Conditions	Yield
With thionyl chloride In chlorobenzene at 110℃; for 3h;	98%
With thionyl chloride In toluene at 90℃;	92.1%
With thionyl chloride; N,N-dimethyl-formamide In 1,2-dichloro-ethane for 5h; Reflux;	90%

3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9) → 1-methyl-3-(difluoromethyl)-1H-pyrazole-4-amide (925689-10-7)

Conditions	Yield
Stage #1: 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 0.5h; Stage #2: With ammonium hydroxide In dichloromethane Cooling with ice;	98%
Multi-step reaction with 2 steps 1: thionyl chloride / 4 h / Reflux 2: ammonium hydroxide / dichloromethane / 4 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: thionyl chloride / 4 h / Reflux 2: ammonium hydroxide / tetrahydrofuran View Scheme
Multi-step reaction with 2 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.5 h / 20 °C 2: ammonium hydroxide / dichloromethane / 0 °C View Scheme
Stage #1: 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: With ammonium hydroxide at 0 - 20℃;

methanol (67-56-1) + 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9) → methyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate

Conditions	Yield
With sulfuric acid at 75℃; for 8h;	97.2%

3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9) + tert-butyl alcohol (75-65-0) → tert-butyl (3-(difluoromethyl)-1-methyl-1H-pyrazol-4-yl)carbamate

Conditions	Yield
With diphenylphosphoranyl azide; N-ethyl-N,N-diisopropylamine at 20 - 90℃; for 4.16667h; Inert atmosphere;	94%
With diphenyl phosphoryl azide; N-ethyl-N,N-diisopropylamine at 20 - 90℃; for 4.16667h; Curtius Rearrangement; Inert atmosphere;	94%
With diphenyl phosphoryl azide; N-ethyl-N,N-diisopropylamine at 20 - 90℃; for 4.5h; Inert atmosphere;	91%

3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9) + 5-amino-9-syn-isopropyl-benzonorbornene → C20H23F2N3O

Conditions	Yield
With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine In dichloromethane at 20℃; for 21h;	92.6%

3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9) + C14H19N → C20H23F2N3O

Conditions	Yield
With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine In dichloromethane at 20℃; for 3h;	91.7%

3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9) → tert-butyl (3-(difluoromethyl)-1-methyl-1H-pyrazol-4-yl)carbamate

Conditions	Yield
With diphenylphosphoranyl azide; N-ethyl-N,N-diisopropylamine In tert-butyl alcohol at 20 - 90℃; for 4.5h; Inert atmosphere;	91%

3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → N-methoxy,N-methyl-1-methyl-3-(difluoromethyl)-1H-pyrazole-4-carboxylic amide

Conditions	Yield
Stage #1: 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride In dichloromethane at 20℃;	91%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃;	91%

3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9) → 3-(difluoromethyl)-4-iodo-1-methyl-1H-pyrazole

Conditions	Yield
With potassium iodate; sulfuric acid; iodine; acetic acid In sulfolane at 45 - 60℃; for 1.33h;	90%
Multi-step reaction with 3 steps 1.1: diphenylphosphoranyl azide; N-ethyl-N,N-diisopropylamine / 4.17 h / 20 - 90 °C / Inert atmosphere 2.1: trifluoroacetic acid / dichloromethane / 2.5 h / 20 °C 3.1: hydrogenchloride; sodium nitrite / water / 1 h / 0 °C 3.2: 0.5 h View Scheme
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine; diphenyl phosphoryl azide / 4.17 h / 20 - 90 °C / Inert atmosphere 2.1: trifluoroacetic acid / dichloromethane / 2.5 h / 20 °C 3.1: hydrogenchloride; sodium nitrite / water / 1 h / 0 °C 3.2: 0.5 h / 20 °C View Scheme

3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (176969-34-9) + C12H17BrN2O2S → N-(2-bromophenyl)-2-(1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylamino)-cyclohexylsulfonamide

Conditions	Yield
Stage #1: 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0℃; for 2h; Inert atmosphere; Stage #2: C12H17BrN2O2S In dichloromethane at 0℃; for 3h; Inert atmosphere;	90%

Upstream product

• 141573-95-7 ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate 
• 1086400-66-9 (Z)-2-(ethoxymethylene)-4,4-difluoro-3-oxobutanoic acid ethyl ester 
• 60-34-4 methylhydrazine 
• 1089212-38-3 4-bromo-3-(difluoromethyl)-1-methyl-1H-pyrazole 
• 201230-82-2 carbon monoxide 
• 1094484-55-5 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde 
• 851725-87-6 ethyl 3-(dichloromethyl)-1-methyl-1H-pyrazole-4-carboxylate 
• 1049772-84-0 3-difluoromethyl-1-methyl-1H-pyrazole-4-carbonitrile 
• 53927-12-1 ethyl-3-(pyrrolidin-1-yl)prop-2-enoate 
• 1550-50-1 1,1,2,2-tetrafluoro-N,N-dimethylethan-1-amine 
• 1001-26-9 ethyl 3-ethoxyacrylate 
• 34846-90-7 methyl 3-methoxyprop-2-enoate 
• 90608-65-4 3-piperidin-1-yl-acrylic acid methyl ester 
• 2925-22-6 2,2-difluoroacetyl fluoride 

Downstream Products

• 141573-96-8 3‐difluoromethyl‐1‐methylpyrazole-4-carbonyl chloride 
• 1105713-20-9 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid [1-methyl-2-(2,4,6-tribromo-phenoxy)-ethyl]amide 
• 1191991-07-7 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid [1-methyl-4-(2,4,6-trichloro-phenyl)-butyl]-amide 
• 1191990-12-1 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid [1-methyl-3-(2,4,6-trichloro-phenyl)-propyl]-amide 
• 874967-67-6 sedaxane 
• 1382600-78-3 benzovindiflupyr 

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The invention relates to a preparation method of a pyrazole derivative. The compound shown in the formula I reacts with a silanization reagent shown in a formula II to generate an intermediate productshown in a formula III, the intermediate product shown in the formula III reacts with a halogenated acid derivative shown in a formula IV to generate a halogenated compound shown in a formula V, andthe halogenated compound shown in the formula V reacts under acidic conditions to generate a pyrazole derivative shown in a formula VI. The preparation method of the pyrazole derivative is suitable for industrial production.

Synthesis and biological activity of acyl thiourea containing difluoromethyl pyrazole motif

A series of new acyl thiourea derivatives containing difluoromethyl pyrazole moiety were designed and synthesized. Their structures were confirmed by 1H NMR, 31C NMR, MS and HRMS. The bioassay results showed that some of title compounds exhibited good in vivo fungicidal activity against Botrytis cinerea and Fusarium oxysporum and good antibacterial activity against Pseudomonas syringae pv. Lachrymans at 50 mg/L respectively.

3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate compounds, and preparation method and application thereof

The invention discloses 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate compounds, and a preparation method and an application thereof. The 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylatecompounds are 2-(benzoyloxy)ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate compounds, and have a structural formula represented by formula (I) shown in the description; and in the formula(I), a substituent group R is a phenyl group or a substituted phenyl group, and a substituent group on the benzene ring of the substituted phenyl group is halogen or a C1-C3 alkyl group. The 2-(benzoyloxy)ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate compounds are new compounds with bactericidal activity, have a good inhibition rate on Fusarium graminerum at the concentration of 50ppm, and provide a basis for research and development of new pesticides.

Preparation method and application of -4- (S)-2-(1H- pyrazolecarboxamide)-P-methylbenzoate compound as well as preparation method and application thereof (by machine translation)

The invention discloses (S)- 2 - (1 a system. H-pyrazol-4 (propyl-formamide)-based) propyl benzoate compound as well as preparation method, (S)- 2 - (1 and application thereofHThe structural formula of the-pyrazol-4-formamide)-based ethyl (I) benzoate compound is shown in a formula shown: in the specification. Substituent groups R in the (I) formula (No.No. STR3No.No., No.No. STR7No.No.No.). 1 The number of substituents on the, phenyl ring, which is a phenyl group or a substituted phenyl group, is, each independently selected from the group consisting of one, C1 - C4 or, more, C1 - C4 substituents, C1 - C3 each; of which R is independently selected from the group consisting of a halogen atom, an alkyl group, an alkyl group, an alkyl group, and a substituted phenyl group. 2 The preparation method of the novel compound with the. bactericidal activity is simple, and the compound obtained by the method, disclosed by the invention, is simple, in preparation method, 50mg/mL and the compound obtained by, the method disclosed by the invention has a good inhibition activity on. cucumber Botrytis cinerea and pathogenic bacteria such as cucumbers. (by machine translation)

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.

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

The invention discloses a preparation method of 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, and belongs to the field of pesticide organic synthesis. The preparation method comprises thefollowing steps: step 1, enabling 1-methyl-3-(trimethylsilyl) pyrazole to react with halogen to obtain 4-halogen-1-methyl-3-(trimethylsilyl) pyrazole; step 2, after exchange is conducted through a Grignard reagent, enabling the 4-halogen-1-methyl-3-(trimethylsilyl) pyrazole to react with chloroformate to obtain 1-methyl-3-trimethylsilyl-1H-pyrazole-4-carboxylic acid; step 3, then carrying out a heating reaction with bromine, so as to obtain 3-bromo-1-methyl-1H-pyrazole-4-carboxylic acid; and step 4, finally, carrying out heating coupling on the 3-bromo-1-methyl-1H-pyrazole-4-carboxylic acid and difluoromethylboronic acid by adopting a palladium catalyst, and performing recrystallization to obtain the 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid. The invention provides a new synthesis path for the synthesis of the compound, and has a potential industrial method prospect.

Method for synthesizing 3- difluoro methyl -1- methyl -1H- pyrazole -4- carboxylic acid by one-pot method

The invention discloses a method for synthesizing 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid by a one-pot method, wherein the method includes the following steps: in xylene, carrying outa condensation reaction of 4,4-difluoroethylacetoacetate and triethyl orthoformate under heating and catalysis of metal carboxylate, cooling, then dropwise adding a methylhydrazine aqueous solution, then heating up, carrying out a ring closing reaction, carrying out saponification and acidification of the obtained ring-closed reaction liquid, and thus obtaining the 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid. The method is reasonable in design, high in yield, simple in process operation, low in cost, and suitable for industrialized production.

METHOD FOR PRODUCING HALOGEN-CONTAINING PYRAZOLE CARBOXYLIC ACID AND INTERMEDIATE THEREOF

The invention provides a method capable of more simply and efficiently producing halogen-containing pyrazolecarboxylic acids and intermediates thereof, which are useful as pharmaceutical or agrochemical intermediates, in a manner suitable for industrial production. In particular, the invention provides a method of producing a compound represented by the formula (b), which comprises reacting a compound represented by the formula (a) with a halogenating agent selected from the group consisting of a compound represented by X2 (formula (1)), a compound represented by SOX2 (formula (2)), and a compound represented by SO2X2 (formula (3)) to obtain the compound represented by the formula (b): formula (1) X2 formula (2) SOX2 formula (3) SO2X2 wherein each symbol is as described in the description.