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inquiry1H-Pyrazole-3-carbonitrile,5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)thio]-Appearance:white crystalline powder Storage:Store in dry, dark and ventilated place Package:25KG drum Application:intermediate Transportation:by a
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Langlois reagent
5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
Conditions | Yield |
---|---|
Stage #1: Langlois reagent; 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole With C7H16O3P(1-)*C6H11N2O(1+) In toluene at -2℃; for 0.0833333h; Stage #2: With phosphorus trichloride In toluene at 50℃; for 5h; Temperature; | 96% |
Stage #1: Langlois reagent; 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole; dimethylamine p-toluenesulfonate In N,N-dimethyl-formamide; toluene at 20 - 25℃; for 0.75h; Stage #2: With phosphorus trichloride In N,N-dimethyl-formamide; toluene at 0 - 70℃; for 8h; Product distribution / selectivity; | 66.7% |
Stage #1: Langlois reagent; 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole; dimethylamine p-toluenesulfonate In N,N-dimethyl-formamide; toluene at 25℃; for 0.75h; Industry scale; Stage #2: With phosphorus trichloride In N,N-dimethyl-formamide; toluene at 0 - 70℃; for 10h; Product distribution / selectivity; |
5-amino-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-4-thiocyanato-1H-pyrazole-3-carbonitrile
Bromotrifluoromethane
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
Conditions | Yield |
---|---|
Stage #1: 5-amino-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-4-thiocyanato-1H-pyrazole-3-carbonitrile With sulfur dioxide; sodium formate In DMF (N,N-dimethyl-formamide) at 20℃; for 0.0833333h; Stage #2: Bromotrifluoromethane In DMF (N,N-dimethyl-formamide) at 20 - 45℃; under 8625.86 Torr; for 1.5h; Product distribution / selectivity; | 90.8% |
Stage #1: 5-amino-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-4-thiocyanato-1H-pyrazole-3-carbonitrile With sulfur dioxide In DMF (N,N-dimethyl-formamide) at 20℃; for 0.0333333h; Stage #2: Bromotrifluoromethane With sodium formate In DMF (N,N-dimethyl-formamide) at 20 - 54℃; for 2.33333h; Product distribution / selectivity; | 84.7% |
With sulfur dioxide; potassium formate In DMF (N,N-dimethyl-formamide); water at -60 - 55℃; for 3h; Product distribution / selectivity; | 81% |
Bromotrifluoromethane
4,4'-dithiobis [5-amino-3-cyano-1-{2,6-dichloro-4-(trifluoromethyl)phenyl}-1H-pyrazole]
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
Conditions | Yield |
---|---|
With sulfur dioxide; sodium formate In N,N-dimethyl-formamide at 60℃; under 9000.7 - 9750.8 Torr; for 4h; Mechanism; Product distribution; other reagent, other perhalogenoalkanes, other disulfide; | 85% |
With sulfur dioxide; sodium formate In N,N-dimethyl-formamide at 60℃; under 9000.7 - 9750.8 Torr; for 4h; | 85% |
With disodium hydrogenphosphate; sodium dithionite In water; N,N-dimethyl-formamide at 20℃; for 4h; | 51% |
Trifluoromethylsulfenyl chloride
5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
Conditions | Yield |
---|---|
In dichloromethane at 18 - 20℃; for 12h; Large scale; | 68% |
With sodium hydroxide In dichloromethane at 10 - 20℃; for 12h; Large scale; | 68% |
In dichloromethane for 2h; Heating; |
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
Conditions | Yield |
---|---|
With copper dichloride In chlorobenzene at 100℃; for 4h; | 65% |
fipronil
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
Conditions | Yield |
---|---|
With trifluoroacetic anhydride; sodium iodide In acetone at 0℃; for 10h; | 60% |
5-amino-3-cyano-4-(trifluoromethylsulfenyl)-1-(2,6-dinitro-4-trifluoromethylphenyl)pyrazole
aminosulfonic acid
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
Conditions | Yield |
---|---|
With lithium chloride In 1-methyl-pyrrolidin-2-one; water | 48% |
Bromotrifluoromethane
sulfur dioxide
4,4'-dithiobis [5-amino-3-cyano-1-{2,6-dichloro-4-(trifluoromethyl)phenyl}-1H-pyrazole]
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
Conditions | Yield |
---|---|
With sodium formate; sodium hydrogencarbonate In water; N,N-dimethyl-formamide |
4,4'-dithiobis [5-amino-3-cyano-1-{2,6-dichloro-4-(trifluoromethyl)phenyl}-1H-pyrazole]
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
Conditions | Yield |
---|---|
In N-methyl-acetamide; water |
2,6-dichloro-4-(trifluoromethyl)aniline
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: nitrosylsulfuric acid; acetic acid / 30 - 55 °C 1.2: 0 - 15 °C 2.1: dichloromethane View Scheme |
1,2-dichloro-4-(trifluoromethyl)benzene
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: dimethylsulfone; potassium fluoride; ammonia / 6 h / 30 - 235 °C / 18751.9 - 19502 Torr / Autoclave 2.1: sulfuryl dichloride; 1-methyl-pyrrolidin-2-one / 1-methyl-pyrrolidin-2-one; chlorobenzene / 8 h / 55 - 60 °C 3.1: nitrosylsulfuric acid; acetic acid / 30 - 55 °C 3.2: 0 - 15 °C 4.1: dichloromethane View Scheme | |
Multi-step reaction with 4 steps 1.1: 1-methyl-pyrrolidin-2-one; potassium fluoride; ammonia / 10 h / 245 - 250 °C / 22502.3 - 30003 Torr / Autoclave 2.1: sulfuryl dichloride; 1-methyl-pyrrolidin-2-one / 1-methyl-pyrrolidin-2-one; chlorobenzene / 8 h / 55 - 60 °C 3.1: nitrosylsulfuric acid; acetic acid / 30 - 55 °C 3.2: 0 - 15 °C 4.1: dichloromethane View Scheme |
chlorothio-trichloro-methane
5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
Conditions | Yield |
---|---|
In dichloromethane | 225 g |
2-chloro-4-(trifluoromethyl)aniline
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sulfuryl dichloride; 1-methyl-pyrrolidin-2-one / 1-methyl-pyrrolidin-2-one; chlorobenzene / 8 h / 55 - 60 °C 2.1: nitrosylsulfuric acid; acetic acid / 30 - 55 °C 2.2: 0 - 15 °C 3.1: dichloromethane View Scheme |
5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
Conditions | Yield |
---|---|
With dimethylamine p-toluenesulfonate; Langlois reagent; trichlorophosphate In N,N-dimethyl-formamide; toluene at 0 - 45℃; for 20h; Reagent/catalyst; Temperature; Solvent; | 4.95 g |
2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene
5-amino-4-((trifluoromethyl)thio)-1H-pyrazole-3-carbonitrile
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; copper In tetrahydrofuran; dimethyl sulfoxide at 60℃; for 8h; Temperature; |
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
fipronil
Conditions | Yield |
---|---|
Stage #1: 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile With dichloro-acetic acid; sulfuric acid at 15℃; for 0.5h; Stage #2: With dihydrogen peroxide In water at 15℃; Product distribution / selectivity; | 98% |
With caro's acid In dichloromethane at 0 - 5℃; Reagent/catalyst; Industrial scale; | 97.9% |
With dihydrogen peroxide In dichloro-acetic acid; water; trichloroacetic acid at 20℃; for 2h; Product distribution / selectivity; | 95% |
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
A
fipronil
B
fipronil sulfone
Conditions | Yield |
---|---|
With dihydrogen peroxide; trifluoroacetic acid In dichloromethane at 10 - 12℃; for 3h; | A 96% B n/a |
Stage #1: 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile With trifluoroacetic acid for 0.25h; Stage #2: With Oxone at -15℃; Product distribution / selectivity; | A 55.4% B n/a |
Stage #1: 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile With trifluoroacetic acid for 0.25h; Industry scale; Stage #2: With Oxone at -15℃; Product distribution / selectivity; Industry scale; |
sulfure de methyle et de 2-chloroethyle
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-(N-methyl-N-(2-methylthioethyl)amino)-4-trifluoromethylthiopyrazole
Conditions | Yield |
---|---|
With potassium phosphate In acetonitrile at 20 - 30℃; for 8h; Conversion of starting material; Heating / reflux; | 89% |
With potassium phosphate In 1-methyl-pyrrolidin-2-one at 20 - 30℃; for 8h; Conversion of starting material; Heating / reflux; | 7 %Spectr. |
With sodium hydride In dimethyl sulfoxide; N,N-dimethyl-formamide at 20 - 30℃; for 8h; Conversion of starting material; Heating / reflux; | 10 %Spectr. |
With sodium hydride In N,N-dimethyl-formamide at 20 - 30℃; for 8h; Conversion of starting material; Heating / reflux; | 10 %Spectr. |
dimethyl cis-but-2-ene-1,4-dioate
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 50℃; for 3h; | 84% |
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
Conditions | Yield |
---|---|
With sulfuric acid In water at 135℃; for 7h; | 82% |
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
acrylic acid methyl ester
5-(2'-bromo-2'-carbomethoxy)ethyl-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylthio-1H-pyrazole-3-carbonitrile
Conditions | Yield |
---|---|
With tert.-butylnitrite; copper(I) bromide In acetonitrile | 78% |
With tert.-butylnitrite; copper(ll) bromide In acetonitrile at 0 - 20℃; for 12h; |
Methoxyacetyl chloride
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
Conditions | Yield |
---|---|
With dmap; triethylamine In chloroform | 52% |
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
fipronil sulfone
Conditions | Yield |
---|---|
With potassium permanganate; magnesium sulfate In water; acetone at 20℃; |
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-trifluoromethylthio-1H-pyrazole-3-carboxaldehyde
Conditions | Yield |
---|---|
aluminum nickel In formic acid | |
aluminum nickel In formic acid |
Ethyl oxalyl chloride
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
Conditions | Yield |
---|---|
With dmap; triethylamine In tetrahydrofuran at 50 - 70℃; for 8h; Heating / reflux; |
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
2-chloropropionyl chloride
Conditions | Yield |
---|---|
With zinc(II) chloride In toluene for 4h; Heating / reflux; |
2-chloropropionyl chloride
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
Conditions | Yield |
---|---|
With zinc(II) chloride In toluene for 16h; Heating / reflux; |
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
isopropyl alcohol
Conditions | Yield |
---|---|
Stage #1: 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile; isopropyl alcohol for 0.0833333h; Stage #2: With formaldehyd at 20℃; for 120h; |
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
dimethyl amine
5-amino-3-cyano-1-[2,6-bis(dimethylamino)-4-trifluoromethylphenyl]-4-trifluoromethylthiopyrazole
Conditions | Yield |
---|---|
In 1,4-dioxane; water at 200℃; for 0.666667h; Microwave irradiation; |
ethanol
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
5-amino-1-(2-chloro-6-ethoxy-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylthiopyrazole
Conditions | Yield |
---|---|
With copper(I) bromide; sodium t-butanolate In DMF (N,N-dimethyl-formamide) at 90℃; for 7h; |
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
methylamine
5-amino-1-(2-chloro-6-methylamino-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylthiopyrazole
Conditions | Yield |
---|---|
In 1,4-dioxane; water at 200℃; for 0.666667h; Microwave irradiation; |
N-Ethylmethylamine
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
A
5-amino-3-cyano-1-[2-chloro-6-(ethyl-methylamino)-4-trifluoromethylphenyl]-4-trifluoromethylthiopyrazole
B
5-amino-3-cyano-1-[2,6-bis(ethyl-methylamino)-4-trifluoromethylphenyl]-4-trifluoromethylthiopyrazole
Conditions | Yield |
---|---|
In 1,4-dioxane at 140 - 145℃; under 12751.3 - 13501.4 Torr; Microwave irradiatio; |
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; trichlorophosphate In 1,2-dichloro-ethane for 7h; Heating / reflux; |
sulfur dioxide
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
fipronil
Conditions | Yield |
---|---|
With dihydrogen peroxide; boric acid; trifluoroacetic acid In chlorobenzene |
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
Conditions | Yield |
---|---|
With hydrogenchloride In orthoformic acid triethyl ester | |
With hydrogenchloride In orthoformic acid triethyl ester |
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
acetyl chloride
5-acetamido-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylthiopyrazole
Conditions | Yield |
---|---|
With pyridine In dichloromethane; acetonitrile | |
With pyridine In dichloromethane; acetonitrile |
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