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CAS No.: | 120067-83-6 |
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Name: | FIPRONIL-SULFIDE |
Article Data: | 22 |
Molecular Structure: | |
Formula: | C12H4 Cl2 F6 N4 S |
Molecular Weight: | 421.153 |
Synonyms: | 1-(2,6-Dichloro-4-trifluoromethylphenyl)-3-cyano-5-amino-4-(trifluoromethylthio)pyrazole;5-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylthiopyrazole;5-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylthio-1H-pyrazole-3-carbonitrile;5-Amino-1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylthio)pyrazole-3-carbonitrile;5-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-(trifluoromethylthio)pyrazole;Fipronil sulfide; MB 45950 |
Density: | 1.761g/cm3 |
Melting Point: | 161-163 °C(Solv: toluene (108-88-3)) |
Boiling Point: | 393.242oC at 760 mmHg |
Flash Point: | 191.626oC |
PSA: | 92.93000 |
LogP: | 5.84488 |
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 |
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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 |
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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 |
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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 |
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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 |
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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 |
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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 |
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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 |
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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 |
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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 |