Welcome to LookChem.com Sign In|Join Free

CAS

  • or

120067-83-6 Suppliers

Post Buying Request

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier
  • 1H-Pyrazole-3-Carbonitrile, 5-Amino-1-[2, 6-Dichloro-4-(Trifluoromethyl)Phenyl]-4-[(Trifluoromethyl)Thio]-

    Cas No: 120067-83-6

  • No Data

  • 1 Metric Ton

  • 1 million Metric Ton/Year

  • COLORCOM LTD.
  • Contact Supplier
  • 120067-83-6 Structure
  • Basic information

    1. Product Name: FIPRONIL-SULFIDE
    2. Synonyms: 1h-pyrazole-3-carbonitrile,5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)s;1H-Pyrazole-3-carbonitrile, 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)thio)-;5-Amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)thio)pyrazole-3-carbonitrile;1-(2,6-Dichloro-4-trifluoroMethylphenyl)-3-cyano-5-aMino-4-(trifluoroMethylthio)pyrazole;5-AMino-1-(2,6-dichloro-4-trifluoroMethylphenyl)-4-trifluoroMethylthio-1H-pyrazole- 3-carbonitrile;5-AMino-3-cyano-1-(2,6-dichloro-4-trifluoroMethylphenyl)-4-(trifluoroMethylthio)pyrazole;MB 45950;Fipronil-sulde
    3. CAS NO:120067-83-6
    4. Molecular Formula: C12H4Cl2F6N4S
    5. Molecular Weight: 421.152
    6. EINECS: N/A
    7. Product Categories: Agro-Products;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
    8. Mol File: 120067-83-6.mol
    9. Article Data: 23
  • Chemical Properties

    1. Melting Point: 161-163 °C(Solv: toluene (108-88-3))
    2. Boiling Point: 393.242oC at 760 mmHg
    3. Flash Point: 191.626oC
    4. Appearance: /
    5. Density: 1.761g/cm3
    6. Vapor Pressure: 0mmHg at 25°C
    7. Refractive Index: 1.592
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. PKA: -4.16±0.20(Predicted)
    11. CAS DataBase Reference: FIPRONIL-SULFIDE(CAS DataBase Reference)
    12. NIST Chemistry Reference: FIPRONIL-SULFIDE(120067-83-6)
    13. EPA Substance Registry System: FIPRONIL-SULFIDE(120067-83-6)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 120067-83-6(Hazardous Substances Data)

120067-83-6 Usage

Description

Fipronil-Sulfide is a member of the pyrazole class, specifically a 1H-pyrazole derivative with substitutions at various positions by different groups. It is a degradation product of the insecticide Fipronil and is also considered a metabolite of the agrochemical fipronil.

Uses

Used in Pesticide Industry:
Fipronil-Sulfide is used as a degradation product for [application reason] in the pesticide industry. As a metabolite of the agrochemical fipronil, it plays a role in the breakdown and environmental impact of the parent compound, Fipronil, which is an insecticide used for controlling a wide range of pests in various agricultural applications.

Check Digit Verification of cas no

The CAS Registry Mumber 120067-83-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,0,0,6 and 7 respectively; the second part has 2 digits, 8 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 120067-83:
(8*1)+(7*2)+(6*0)+(5*0)+(4*6)+(3*7)+(2*8)+(1*3)=86
86 % 10 = 6
So 120067-83-6 is a valid CAS Registry Number.
InChI:InChI=1/C12H4Cl2F6N4S/c13-5-1-4(11(15,16)17)2-6(14)8(5)24-10(22)9(7(3-21)23-24)25-12(18,19)20/h1-2H,22H2

120067-83-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name fipronil-sulfide

1.2 Other means of identification

Product number -
Other names Fipronil sulfide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:120067-83-6 SDS

120067-83-6Synthetic route

Langlois reagent
2926-29-6

Langlois reagent

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

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
120067-83-6

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile

Conditions
ConditionsYield
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
120069-10-5

5-amino-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-4-thiocyanato-1H-pyrazole-3-carbonitrile

Bromotrifluoromethane
75-63-8

Bromotrifluoromethane

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
120067-83-6

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile

Conditions
ConditionsYield
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
75-63-8

Bromotrifluoromethane

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

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
120067-83-6

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile

Conditions
ConditionsYield
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
421-17-0

Trifluoromethylsulfenyl chloride

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

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
120067-83-6

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile

Conditions
ConditionsYield
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;
Reaxys ID: 12045767

Reaxys ID: 12045767

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
120067-83-6

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile

Conditions
ConditionsYield
With copper dichloride In chlorobenzene at 100℃; for 4h;65%
fipronil
120068-37-3

fipronil

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
120067-83-6

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile

Conditions
ConditionsYield
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
183288-98-4

5-amino-3-cyano-4-(trifluoromethylsulfenyl)-1-(2,6-dinitro-4-trifluoromethylphenyl)pyrazole

aminosulfonic acid
5329-14-6

aminosulfonic acid

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
120067-83-6

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile

Conditions
ConditionsYield
With lithium chloride In 1-methyl-pyrrolidin-2-one; water48%
Bromotrifluoromethane
75-63-8

Bromotrifluoromethane

sulfur dioxide
7446-09-5

sulfur dioxide

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

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
120067-83-6

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile

Conditions
ConditionsYield
With sodium formate; sodium hydrogencarbonate In water; N,N-dimethyl-formamide
CF3 Br

CF3 Br

sodium hydrogen phosphate 12H2 O

sodium hydrogen phosphate 12H2 O

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

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
120067-83-6

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile

Conditions
ConditionsYield
In N-methyl-acetamide; water
2,6-dichloro-4-(trifluoromethyl)aniline
24279-39-8

2,6-dichloro-4-(trifluoromethyl)aniline

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
120067-83-6

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile

Conditions
ConditionsYield
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
328-84-7

1,2-dichloro-4-(trifluoromethyl)benzene

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
120067-83-6

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile

Conditions
ConditionsYield
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
594-42-3

chlorothio-trichloro-methane

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

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
120067-83-6

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile

Conditions
ConditionsYield
In dichloromethane225 g
2-chloro-4-(trifluoromethyl)aniline
39885-50-2

2-chloro-4-(trifluoromethyl)aniline

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
120067-83-6

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile

Conditions
ConditionsYield
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
120068-79-3

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
120067-83-6

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile

Conditions
ConditionsYield
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
118754-53-3

2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene

5-amino-4-((trifluoromethyl)thio)-1H-pyrazole-3-carbonitrile
183288-97-3

5-amino-4-((trifluoromethyl)thio)-1H-pyrazole-3-carbonitrile

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
120067-83-6

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile

Conditions
ConditionsYield
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
120067-83-6

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile

fipronil
120068-37-3

fipronil

Conditions
ConditionsYield
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
120067-83-6

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile

A

fipronil
120068-37-3

fipronil

B

fipronil sulfone
120068-36-2

fipronil sulfone

Conditions
ConditionsYield
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
542-81-4

sulfure de methyle et de 2-chloroethyle

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
120067-83-6

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
847779-93-5

1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-(N-methyl-N-(2-methylthioethyl)amino)-4-trifluoromethylthiopyrazole

Conditions
ConditionsYield
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
624-48-6

dimethyl cis-but-2-ene-1,4-dioate

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
120067-83-6

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile

C18H11ClF6N4O4S

C18H11ClF6N4O4S

Conditions
ConditionsYield
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
120067-83-6

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile

5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylthio-1H-pyrazole-3-carboxylic acid

5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylthio-1H-pyrazole-3-carboxylic acid

Conditions
ConditionsYield
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
120067-83-6

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

5-(2'-bromo-2'-carbomethoxy)ethyl-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylthio-1H-pyrazole-3-carbonitrile
192988-64-0

5-(2'-bromo-2'-carbomethoxy)ethyl-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylthio-1H-pyrazole-3-carbonitrile

Conditions
ConditionsYield
With tert.-butylnitrite; copper(I) bromide In acetonitrile78%
With tert.-butylnitrite; copper(ll) bromide In acetonitrile at 0 - 20℃; for 12h;
Methoxyacetyl chloride
38870-89-2

Methoxyacetyl chloride

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
120067-83-6

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile

1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfenyl-5-(methoxyacetamido)pyrazole

1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfenyl-5-(methoxyacetamido)pyrazole

Conditions
ConditionsYield
With dmap; triethylamine In chloroform52%
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
120067-83-6

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile

fipronil sulfone
120068-36-2

fipronil sulfone

Conditions
ConditionsYield
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
120067-83-6

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
120068-75-9

5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-trifluoromethylthio-1H-pyrazole-3-carboxaldehyde

Conditions
ConditionsYield
aluminum nickel In formic acid
aluminum nickel In formic acid
Ethyl oxalyl chloride
4755-77-5

Ethyl oxalyl chloride

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
120067-83-6

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile

1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-(ethoxycarbonyl)carbonylamino-4-trifluoromethylthiopyrazole

1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-(ethoxycarbonyl)carbonylamino-4-trifluoromethylthiopyrazole

Conditions
ConditionsYield
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
120067-83-6

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile

2-chloropropionyl chloride
625-36-5

2-chloropropionyl chloride

3-chloropropionylamino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylthiopyrazole

3-chloropropionylamino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylthiopyrazole

Conditions
ConditionsYield
With zinc(II) chloride In toluene for 4h; Heating / reflux;
2-chloropropionyl chloride
7623-09-8

2-chloropropionyl chloride

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
120067-83-6

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile

5-(2-chloropropionylamino)-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylthiopyrazole

5-(2-chloropropionylamino)-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylthiopyrazole

Conditions
ConditionsYield
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
120067-83-6

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile

isopropyl alcohol
67-63-0

isopropyl alcohol

1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-isopropyloxymethylamino-4-trifluoromethylthiopyrazole

1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-isopropyloxymethylamino-4-trifluoromethylthiopyrazole

Conditions
ConditionsYield
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
120067-83-6

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile

dimethyl amine
124-40-3

dimethyl amine

5-amino-3-cyano-1-[2,6-bis(dimethylamino)-4-trifluoromethylphenyl]-4-trifluoromethylthiopyrazole
865854-41-7

5-amino-3-cyano-1-[2,6-bis(dimethylamino)-4-trifluoromethylphenyl]-4-trifluoromethylthiopyrazole

Conditions
ConditionsYield
In 1,4-dioxane; water at 200℃; for 0.666667h; Microwave irradiation;
ethanol
64-17-5

ethanol

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
120067-83-6

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
865854-38-2

5-amino-1-(2-chloro-6-ethoxy-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylthiopyrazole

Conditions
ConditionsYield
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
120067-83-6

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile

methylamine
74-89-5

methylamine

5-amino-1-(2-chloro-6-methylamino-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylthiopyrazole
865854-36-0

5-amino-1-(2-chloro-6-methylamino-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylthiopyrazole

Conditions
ConditionsYield
In 1,4-dioxane; water at 200℃; for 0.666667h; Microwave irradiation;
N-Ethylmethylamine
624-78-2

N-Ethylmethylamine

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
120067-83-6

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
865854-58-6

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
865854-42-8

5-amino-3-cyano-1-[2,6-bis(ethyl-methylamino)-4-trifluoromethylphenyl]-4-trifluoromethylthiopyrazole

Conditions
ConditionsYield
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
120067-83-6

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile

5-(dichlorophosphorylamino)-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylthiopyrazole

5-(dichlorophosphorylamino)-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylthiopyrazole

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; trichlorophosphate In 1,2-dichloro-ethane for 7h; Heating / reflux;
sulfur dioxide
7446-09-5

sulfur dioxide

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
120067-83-6

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile

fipronil
120068-37-3

fipronil

Conditions
ConditionsYield
With dihydrogen peroxide; boric acid; trifluoroacetic acid In chlorobenzene
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
120067-83-6

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile

3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-ethoxymethylideneamino-4-trifluoromethylthiopyrazole

3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-ethoxymethylideneamino-4-trifluoromethylthiopyrazole

Conditions
ConditionsYield
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
120067-83-6

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile

acetyl chloride
75-36-5

acetyl chloride

5-acetamido-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylthiopyrazole
120068-03-3

5-acetamido-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylthiopyrazole

Conditions
ConditionsYield
With pyridine In dichloromethane; acetonitrile
With pyridine In dichloromethane; acetonitrile

120067-83-6Relevant articles and documents

Synthesis of fipronil sulfide, an active metabolite, from the parent insecticide fipronil

Beeler, Aaron B.,Schlenk, Daniel K.,Rimoldi, John M.

, p. 5371 - 5372 (2001)

A convenient procedure for the synthesis of fipronil sulfide, one of several active metabolites identified from the insecticide fipronil, has been developed. Reduction of fipronil with trifluoroacetic anhydride-sodium iodide in acetone, followed by flash chromatography afforded fipronil sulfide in 60% yield and >99.9 percent purity. This represents the first direct synthesis of this key metabolite from fipronil.

A convenient conversion of pyrazolyl disulfide to sulfides by sodium dithionite and synthesis of sulfoxides

Tang, Ri-Yuan,Zhong, Ping,Lin, Qiu-Lian

, p. 948 - 953 (2006)

Indirectly introduce trifluoromethylthio-, alkylthio-, and trifluoromethylsulfinyl to pyrazole ring by a convenient reaction of a pyrazolyl disulfide with F3CBr and alkyl halides in the presence of sodium dithionite at room temperature. Followed by selective oxidation with H2O2 or trichloroisocyanuric acid (TCCA) to give trifluoromethylsulfenyl phenylpyrazole, alkylsulfenyl phenylpyazole, trifluoromethylsulfinyl phenylpyrazole 4a (a highly efficient insecticide named fipronil) and ethylsulfinyl phenylpyrazole 4c derivatives, respectively.

Method for preparing fipronil

-

Paragraph 0007; 0008; 0009; 0010; 0011; 0012, (2019/01/23)

The invention relates to a method for preparing fipronil. The method comprises the following steps: taking 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene as an initial raw material, reacting the initial raw material with 5-amino-4-((trifluoromethyl)sulfenyl)-1H-pyrazol-3-formonitrile, wherein the product does not need to be treated; and further reacting to obtain the target product fipronil. Compared with the traditional synthetic method, the method disclosed by the invention takes Cu as a catalyst, and is more efficient and relatively high in yield. Moreover, the operating method is simple and convenient, and the reaction conditions are mild.

Preparation method of 5-amino-1-(2,6-dihydro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylmercapto)-1H-parazole-3-nitrile

-

Paragraph 0028; 0029, (2016/12/07)

The invention discloses a preparation method of 5-amino-1-(2,6-dihydro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylmercapto)-1H-parazole-3-nitrile, which comprises the following steps: (1) adding 5-amino-3-cyano-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-parazole, trifluoromethyl sulfinate, an organic solvent, and a phosphorus-containing iminazole liquid to a reactor, mixing under stirring, and cooling the mixture in an ice bath; and (2) dropwise adding phosphorus trihalide or an organic solution of phosphorus trihalide to the reactor under stirring, reacting at 30-60 DEG C for 1-5h under stirring, quenching the reaction with ice water, extracting with an extracting agent, washing, drying and concentrating to obtain 5-amino-1-(2,6-dihydro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylmercapto)-1H-parazole-3-nitrile. The method is simple and convenient to operate, and can obtain the effects of good yield and purity, etc.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 120067-83-6