120068-79-3

Basic information

• Product Name: 5-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole
• Synonyms: 5-AMINO-1-(2,6-DICHLORO-4-(TRIFLUOROMETHYL)PHENYL)-1H-PYRAZOLE-3-CARBONITRILE;5-AMINO-1-(2,6-DICHLORO-4-TRIFLUOROMETHYLPHENYL)-3-CYCANO PYRAZOLE;5-AMINO-3-CYANO-1-(2,6-DICHLORO-4-TRIFLUOROMETHYLPHENYL)-1H-PYRAZOLE;5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole;FIPRONIL INTERMEDIATE;5-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyanopyrazole;5-Amino-3-cyano-(2,6-dichloro-4-trifluoromethyl-phenyl)pyrazole;5-AMino-3-Cyano-l-(2,6-dichloro-4-trifluoroMethylphenyl)pyrazole
• CAS NO: 120068-79-3
• Molecular Formula: C₁₁H₅Cl₂F₃N₄
• Molecular Weight: 321.09
• Mol File: 120068-79-3.mol
• Article Data: 27

Chemical Properties

• Melting Point: 132-141 °C
• Boiling Point: 433 °C at 760 mmHg
• Flash Point: 215.6 °C
• Appearance: /
• Density: 1.65 g/cm³
• Vapor Pressure: 1.06E-07mmHg at 25°C
• Refractive Index: 1.62
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: -1.27±0.14(Predicted)
• CAS DataBase Reference: 5-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole(120068-79-3)
• EPA Substance Registry System: 5-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole(120068-79-3)

Safety Data

• Hazardous Substances Data: 120068-79-3(Hazardous Substances Data)

Usage

Description

5-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole is a chemical compound characterized by its unique molecular structure, which features a pyrazole ring with an amino group at the 5th position, a cyano group at the 3rd position, and a 2,6-dichloro-4-trifluoromethylphenyl group attached to the 1st position. 5-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole is known for its potential applications in various industries due to its specific chemical properties.

Uses

Used in Pharmaceutical Industry:
5-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole is used as an intermediate in the synthesis of various pharmaceutical compounds, particularly those targeting GABA receptors. Its unique structure allows it to interact with these receptors, making it a valuable component in the development of new drugs for treating neurological disorders and conditions.
Used in Insecticide Production:
In the agricultural industry, 5-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole serves as a key intermediate in the production of Fipronil (F342200), a widely used insecticide. Fipronil is a GABA receptor antagonist that effectively controls a broad spectrum of insects, making it a crucial component in modern pest management strategies.
Used in Chemical Research:
5-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole is also utilized in chemical research and development, where its unique properties can be explored for the creation of new compounds with potential applications in various fields. Researchers can use this compound as a starting point for designing new molecules with specific functions and properties, contributing to the advancement of chemical science and technology.

InChI:InChI=1/C11H5Cl2F3N4/c12-7-1-5(11(14,15)16)2-8(13)10(7)20-9(18)3-6(4-17)19-20/h1-3H,18H2

Synthetic route

2-(2, 6-Dichloro-4-trifluoromethylphenylhydrazono)succinonitrile (213132-03-7) → 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3)

Conditions	Yield
With ammonia In ethanol; water at 0℃; for 0.166667h;	97%
With sodium hydroxide; sodium hydrogencarbonate; sodium carbonate In dichloromethane
With ammonium hydroxide In ethanol at 10 - 15℃; for 10h; pH=>= 11;

syn-2-(2, 6-Dichloro-4-trifluoromethylphenylhydrazono)succinonitrile → 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3)

Conditions	Yield
With ammonia In ethanol; water	97%

5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-carboethoxypyrazole (213457-39-7) → 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3)

Conditions	Yield
With water In 5,5-dimethyl-1,3-cyclohexadiene for 2h; Reagent/catalyst; Reflux;	96.63%

ethyl 2,3-dicyanopropanoate (40497-11-8) + 2,6-dichloro-4-(trifluoromethyl)aniline (24279-39-8) → 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3)

Conditions	Yield
Stage #1: 2,6-dichloro-4-(trifluoromethyl)aniline With nitrosylsulfuric acid; acetic acid at 5 - 50℃; for 11h; Large scale; Stage #2: ethyl 2,3-dicyanopropanoate In water at 10 - 30℃; for 20h; Large scale;	95%
Stage #1: 2,6-dichloro-4-(trifluoromethyl)aniline With nitrosylsulfuric acid; sulfuric acid In hexane at 10 - 30℃; Stage #2: ethyl 2,3-dicyanopropanoate In hexane at 0 - 30℃; for 6h; Solvent;	95.2%
Stage #1: 2,6-dichloro-4-(trifluoromethyl)aniline With hydrogenchloride; sulfuric acid In water; toluene at 30 - 40℃; for 1.5h; Green chemistry; Stage #2: With sodium nitrite In water; toluene at 15 - 20℃; for 1h; Green chemistry; Stage #3: ethyl 2,3-dicyanopropanoate In water; toluene at 10 - 25℃; for 12h; Temperature; Green chemistry;	90%

C14H9Cl2F3N4O2 → 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3)

Conditions	Yield
With urea In ethanol at 25 - 35℃; pH=12 - 13; Large scale;	90.85%

2,3-dicyanopropionic acid methyl ester (61760-68-7) + 2,6-dichloro-4-(trifluoromethyl)aniline (24279-39-8) → 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3)

Conditions	Yield
Stage #1: 2,6-dichloro-4-(trifluoromethyl)aniline With hydrogenchloride; sulfuric acid In water; toluene at 30 - 50℃; for 1h; Green chemistry; Stage #2: With sodium nitrite In water; toluene at 15 - 20℃; for 4h; Green chemistry; Stage #3: 2,3-dicyanopropionic acid methyl ester In water; toluene at 10 - 25℃; for 12.5h; Green chemistry;	85%

2-butynedinitrile (1071-98-3) + 2,6-dichloro-4-(trifluoromethyl)phenyl hydrazine (86398-94-9) → 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3)

Conditions	Yield
In chloroform at 20 - 50℃; for 3.5h;	81%

ethyl 2,3-dicyanopropanoate (40497-11-8) + C7H2Cl2F3N2(1+)*Cl(1-) → 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3)

Conditions	Yield
for 2h;	74.7%
Stage #1: ethyl 2,3-dicyanopropanoate; C7H2Cl2F3N2(1+)*Cl(1-) for 2h; Stage #2: With ammonium hydroxide at 20℃; for 2h; pH=9 - 10;	48.8%

chloromaleo(fumaro)nitrile (26459-70-1) + 2,6-dichloro-4-(trifluoromethyl)phenyl hydrazine (86398-94-9) → 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3)

Conditions	Yield
With 2,6-dimethylpyridine In methanol at 20 - 25℃;	71%

N'-(2,6-dichloro-4-trifluoromethylphenyl)-chloroacetohydrazonoyl chloride (288066-46-6) → 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3)

Conditions	Yield
In ethanol; water	53%

2-methoxyethyl cyanoacetate (10258-54-5) → 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3)

Conditions	Yield
Stage #1: 2-methoxyethyl cyanoacetate With hydrogenchloride; 2,6-dichloro-4-(trifluoromethyl)aniline; sodium nitrite In 2-methoxy-ethanol for 3h; Stage #2: pH=9;

5-amino-3-chloro-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-ethoxycarbonylpyrazole (120068-87-3) + 1,1-dichloroheptane (821-25-0) → 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3)

Conditions	Yield
In 1,4-dioxane; hydrogenchloride; acetic acid

1,2-dichloro-4-(trifluoromethyl)benzene (328-84-7) → 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3)

Conditions	Yield
Multi-step reaction with 3 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 View Scheme
Multi-step reaction with 3 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 View Scheme

2-chloro-4-(trifluoromethyl)aniline (39885-50-2) → 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3)

Conditions	Yield
Multi-step reaction with 2 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 View Scheme

2,6-dichloro-4-(trifluoromethyl)aniline (24279-39-8) → 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogenchloride; sodium nitrite; ethanol / water / 0.5 h / Cooling with ice 2.1: 2 h 2.2: 2 h / 20 °C / pH 9 - 10 View Scheme
Multi-step reaction with 2 steps 1: hydrogenchloride; sodium nitrite / ethanol; water / 0.5 h / Cooling with ice 2: 2 h View Scheme
Multi-step reaction with 2 steps 1.1: hydrogenchloride / ethanol / 0.5 h 1.2: 0 - 10 °C 1.3: 0 - 15 °C / pH 12 2.1: hydrogenchloride / water / 80 °C / pH Ca. 7 View Scheme

ethanol (64-17-5) + C14H9Cl2F3N4O2 → 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3) + Diethyl carbonate (105-58-8)

Conditions	Yield
With hydrogenchloride In water at 80℃; pH=Ca. 7;	A 6.1 g B 40.78 g

methanol (67-56-1) + C14H9Cl2F3N4O2 → ethyl methyl carbonate (623-53-0) + 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3)

Conditions	Yield
With hydrogenchloride In water at 80℃; pH=Ca. 7;	A 37.6 g B 5.8 g

Reaxys ID: 35961796 + Reaxys ID: 35961797 → Reaxys ID: 35961795 + 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3)

4-trifluoromethylphenylamine (455-14-1) → 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogenchloride; sodium nitrite / ethanol; water / 12 h / -5 - 5 °C 2: 2,2'-azobis(isobutyronitrile); chlorine / 1,2-dichloro-ethane / 8 h / 15 - 80 °C 3: water / 5,5-dimethyl-1,3-cyclohexadiene / 2 h / Reflux View Scheme

trifluoromethylsulfinyl chloride (20621-29-8) + 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3) → fipronil (120068-37-3)

Conditions	Yield
With dimethylamine p-toluenesulfonate for 10h; Heating;	99%
With dimethylamine p-toluenesulfonate at 50℃; for 8h;	92%
With benzyltrimethylammonium chloride In 1,2-dichloro-ethane at 35℃; for 2h; Temperature; Industrial scale;	90.3%

Langlois reagent (2926-29-6) + 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3) → 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile (120067-83-6)

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-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3) → 4,4'-dithiobis [5-amino-3-cyano-1-{2,6-dichloro-4-(trifluoromethyl)phenyl}-1H-pyrazole] (130755-46-3)

Conditions	Yield
With disulfur dichloride In dichloromethane at 20℃;	95%
With disulfur dichloride In dichloromethane at 0 - 20℃;	95%
With disulfur dichloride In dichloromethane at 0 - 20℃;

bis(4-fluorophenyl)disulfide (405-31-2) + 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3) → C17H8Cl2F4N4S (1158997-67-1)

Conditions	Yield
With ferric(III) bromide; iodine In acetonitrile at 80℃; for 42h; regioselective reaction;	95%

1-Bromopentane (110-53-2) + 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3) → N-5-pentylamino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-1H-pyrazole

Conditions	Yield
With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 3h; Sonication; Microwave irradiation; Heating;	94.1%

5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3) → 5-amino-4-chloro-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-1H-pyrazole-3-carbonitrile

Conditions	Yield
With N-chloro-succinimide In acetonitrile at 20℃; for 1h;	94%

4,4'-dichlorodiphenyl disulfide (1142-19-4) + 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3) → 5-amino-4-[(4-chlorophenyl)thio]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1H-pyrazole-3-carbonitrile (1158997-68-2)

Conditions	Yield
With ferric(III) bromide; iodine In acetonitrile at 80℃; for 42h; regioselective reaction;	93%
With ferric(III) bromide; iodine In acetonitrile at 85℃; for 30h;	81%

benzyl bromide (100-39-0) + 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3) → N-5-benzylamino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-1H-pyrazole

Conditions	Yield
With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 3h; Sonication; Microwave irradiation; Heating;	92.6%

di(p-tolyl) disulfide (103-19-5) + 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3) → 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(p-tolylthio)-1H-pyrazole-3-carbonitrile (1158997-61-5)

Conditions	Yield
With ferric(III) bromide; iodine In acetonitrile at 80℃; for 42h; regioselective reaction;	92%
With ferric(III) bromide; iodine In acetonitrile at 85℃; for 36h;	81%

dibenzyl disulphide (150-60-7) + 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3) → 5-amino-4-(benzylthio)-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1H-pyrazole-3-carbonitrile

Conditions	Yield
With ferric(III) bromide; iodine In acetonitrile at 80℃; for 42h; regioselective reaction;	90%
With ferric(III) bromide; iodine In acetonitrile at 85℃; for 16h;	79%

methanesulfonyl chloride (124-63-0) + 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3) → 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-di(methylsulfonyl)amide-1H-pyrazole-3-carbonitrile (849950-10-3)

Conditions	Yield
With pyridine at 20℃;	88.7%

trifluoromethylsulfinyl chloride (20621-29-8) + dimethylamine p-toluenesulfonate (2840-22-4) + 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3) → fipronil (120068-37-3)

Conditions	Yield
In water; toluene	88%

4-methoxyphenylboronic acid (5720-07-0) + 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3) → 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(4-methoxyphenyl)-1H-pyrazole-3-carbonitrile

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; N-iodo-succinimide; sodium hydrogencarbonate In ethanol; water at 80℃; for 18h; Inert atmosphere;	88%

diphenyldisulfane (882-33-7) + 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3) → 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(phenylthio)-1H-pyrazole-3-carbonitrile (1127335-86-7)

Conditions	Yield
With ferric(III) bromide; iodine In acetonitrile at 85℃; for 26h;	88%
With ferric(III) bromide; iodine In acetonitrile at 80℃; for 42h; regioselective reaction;	82%

4-Ethynylbenzaldehyde (63697-96-1) + 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3) → 1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-5-(4-ethynylbenzylideneamino)-1H-pyrazole-3-carbonitrile

Conditions	Yield
With hydrogenchloride In water for 48h; Ionic liquid;	88%

5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3) → 3-cyano-4-bromo-5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-1H-pyrazole

Conditions	Yield
With N-Bromosuccinimide In acetonitrile at 50℃; for 1h;	87%

4-methylphenylboronic acid (5720-05-8) + 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3) → 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-p-tolyl-1H-pyrazole-3-carbonitrile

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; N-iodo-succinimide; sodium hydrogencarbonate In ethanol; water at 80℃; for 18h; Inert atmosphere;	87%

benzenesulfonyl chloride (98-09-9) + 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3) → 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-phenylsulfonylamino-1H-pyrazole-3-carbonitrile (912462-94-3)

Conditions	Yield
With pyridine at 20℃;	86.5%

4-ethylphenylboronic acid (63139-21-9) + 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3) → 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(4-ethylphenyl)-1H-pyrazole-3-carbonitrile (1373210-80-0)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; N-iodo-succinimide; sodium hydrogencarbonate In ethanol; water at 80℃; for 18h; Inert atmosphere;	86%

p-toluenesulfonyl chloride (98-59-9) + 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3) → 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(4-methylphenylsulfonylamino)-1H-pyrazole-3-carbonitrile (901418-28-8)

Conditions	Yield
With pyridine at 20℃;	85.2%

5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3) → 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-iodo-1H-pyrazole-3-carbonitrile (188539-59-5)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; N-iodo-succinimide; copper(l) iodide; caesium carbonate In dimethyl sulfoxide at 100℃; for 18h; Solvent; Schlenk technique;	85%
With N-iodo-succinimide In acetonitrile
With N-iodo-succinimide In acetonitrile for 1h; Heating;

5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3) + phenylboronic acid (98-80-6) → 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-phenyl-1H-pyrazole-3-carbonitrile

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; N-iodo-succinimide; sodium hydrogencarbonate In ethanol; water at 80℃; for 18h; Inert atmosphere;	85%

4-n-chlorophenylacetylene (873-73-4) + 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3) → 5-amino-4-((4-chlorophenyl)ethynyl)-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; N-iodo-succinimide; copper(l) iodide; caesium carbonate In ethanol; water at 100℃; for 18h; Schlenk technique; Green chemistry;	85%

4-methoxy-phenyl-sulphonyl chloride (98-68-0) + 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3) → 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(4-methoxyphenylsulfonylamino)-1H-pyrazole-3-carbonitrile (870087-78-8)

Conditions	Yield
With pyridine at 20℃;	84.5%

Upstream product

• 40497-11-8 ethyl 2,3-dicyanopropanoate 
• 24279-39-8 2,6-dichloro-4-(trifluoromethyl)aniline 
• 455-14-1 4-trifluoromethylphenylamine 
• 213457-39-7 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-carboethoxypyrazole 
• 67-56-1 methanol 
• 64-17-5 ethanol 
• 61760-68-7 2,3-dicyanopropionic acid methyl ester 
• 39885-50-2 2-chloro-4-(trifluoromethyl)aniline 
• 328-84-7 1,2-dichloro-4-(trifluoromethyl)benzene 
• 26459-70-1 chloromaleo(fumaro)nitrile 
• 86398-94-9 2,6-dichloro-4-(trifluoromethyl)phenyl hydrazine 
• 120068-87-3 5-amino-3-chloro-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-ethoxycarbonylpyrazole 
• 821-25-0 1,1-dichloroheptane 
• 288066-46-6 N'-(2,6-dichloro-4-trifluoromethylphenyl)-chloroacetohydrazonoyl chloride 

Downstream Products

• 315208-01-6 N-[3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole-5-yl]pyrazine-2-carboxamide 
• 120067-92-7 5-amino-3-cyano-4-dichlorofluoromethylthio-1-(2,6-dichloro-4-trifluoromethylphenyl)-1-H-pyrazole 
• 169046-52-0 5-(N-trifluoromethylsulfinyl)-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole 
• 120068-37-3 fipronil 
• 1373210-81-1 5-amino-4-(4-chloro-2-methoxyphenyl)-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile 
• 1373210-80-0 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(4-ethylphenyl)-1H-pyrazole-3-carbonitrile 
• 120067-83-6 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile 

Relevant articles and documents

Design, synthesis, crystal structure and bioactivity evaluation of novel diethyl (arylfuranyl)(arylpyrazolylamino)methanephosphonates

Aseries of novel arylpyrazole derivatives containing aminomethanephosphonate and phenylfuran moieties were designed, synthesized and characterized by 1H NMR, 31P NMR and IR spectroscopy and elemental analyses. The single crystal structure of diethyl [5-(4-chlorophenyl)furan-2-yl][3-cyano-1-(2,3,4-trifluorophenyl)- 1H-pyrazol-5-ylamino]methanephosphonate (4l)was determined by X-ray diffraction. Preliminary bioassays showed that these phosphonates exhibit satisfactory insecticidal activities against Culexpipiens and Musca domestica at 0.1%. In particular, compound 4l exhibited a most promising KT50 value, which is superior to that of Dextraltetramethrin and similar to Prallehtrin. The structure-activity relationship was also preliminarily investigated.

Production method of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole

The invention provides a production method of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole. The production method of the 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole comprises the following steps: (1) adding nitrosyl sulfuric acid into a four-necked bottle, and adding mixed liquid of 4-amino-3,5-dichlorobenzotrifluoride and an organic solvent dropwise to produce diazonium liquid; (2) adding the diazonium liquid back into ice water, conducting stirring, standing for layering, separating out a water layer, and adding ethyl 2,3-dicyanopropionate dropwise for coupling; and (3) conducting toluene extraction and combining, adding ammonium hydroxide dropwise for cyclization, and conducting filtering, washing and drying to obtain a finished product. According to the production method of the 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole, the yield is high, the quality is good, single impurity is lower than or equal to 0.1%, the level ofdifficulty of treating three waste is effectively lowered, discharge of the three waste is reduced, and the cost is low.

Method for synthesizing aryl pyrazonitrile and by-producing carbonic acid diester

The invention discloses a method for synthesizing aryl pyrazonitrile and by-producing carbonic acid diester. The method comprises the steps: taking 2,6-dichloro-4-trifluoromethylaniline, 2,3-dicyanopropionate and nitrite as main raw materials, carrying out diazotization and coupling reaction in a solvent containing fatty alcohol, adding a reaction terminating agent after coupling, and then carrying out alcoholysis and cyclization under an alkaline condition to generate aryl pyrazonitrile and carbonic acid diester. Different raw materials and process conditions are selected, the quality and theyield of the aryl pyrazonitrile are not influenced, and the generated by-product is purposefully controlled, so that after the cyclization liquid for synthesizing aryl pyrazonitrile is distilled andseparated, the distillate is subjected to multi-stage rectification, and solvents (methanol, ethanol or propanol and the like) can be recycled; meanwhile, carbonic acid diester of which the quality meets the industrial standard is obtained, and reduction and resource utilization of aryl pyrazonitrile synthesis waste liquid are realized.

Synthesis method of 5-amidogen-3-cyano-1-(2,6-dichloro-4-trifluoromethyl phenyl) pyrazole

The invention discloses a synthesis method of 5-amidogen-3-cyano-1-(2,6-dichloro-4-trifluoromethyl phenyl) pyrazole. The synthesis method comprises the following steps that at 0 to 5 DEG C, an ethanol solution of 2,6-dichloro-4-trifluoromethyl aniline salt and a sodium nitrite solution with the mass concentration being 40 to 45 percent are simultaneously and dropwise added into a hydrochloric acid ethanol solution of 2,3-dicyan ethyl propionate; reaction liquid is subjected to heat insulation for 2 to 12h at 0 to 5 DEG C until the concentration of 2,6-dichloro-4-trifluoromethyl aniline in the reaction liquid is smaller than or equal to 0.5 percent; reducing reagents are dropwise added into the reaction liquid to remove excessive nitrous acid in the reaction liquid until the nitrous acid in the reaction liquid is completely removed; at 10 to 15 DEG C, ammonium hydroxide and ethanol are added into the reaction liquid, so that the pH of the reaction liquid is greater than or equal to 11; heat insulation is performed for 8 to 24h. The synthesis method has the advantages that the technology prejudice of technicians in the field is broken; the cost is reduced; the generation of three wastes is greatly reduced.