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120068-37-3

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  • Factory supply high quality powerful agrochemical lnsecticide Fipronil,120068-37-3 with reasonable price on

    Cas No: 120068-37-3

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  • Factory Supply fipronil (ISO); (±)-5-amino-1-(2,6-dichloro-α,α,α-trifluoro-para-tolyl)-4-trifluoromethylsulfinyl-pyrazole-3-carbonitrile

    Cas No: 120068-37-3

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120068-37-3 Usage

Description

Fipronil is a white powder with a mouldy odour. It has a low solubility in water and is a slow-acting poison. It does not bind strongly with soil, and the half-life of fipronil– sulphone is 34 days. Fipronil is a broadspectrum insecticide of the phenylpyrazole group. Fipronil was first used extensively for the control of ants, beetles, cockroaches, fleas; ticks, termites, mole crickets, thrips, rootworms, weevils, flea of pets, field pest of corn, golf courses, and commercial turf, and other insects. Fipronil was first used in the United States in 1996. Fipronil is a topical insecticide. It kills adult fleas and larvae, ticks, and chewing lice. As a liquid, fipronil is applied on the back side skin of dogs and cats. Reports indicate that some animals do become hypersensitive (allergic) to fipronil.

Chemical Properties

Different sources of media describe the Chemical Properties of 120068-37-3 differently. You can refer to the following data:
1. White crystalline solid.
2. White SOlid

Uses

Different sources of media describe the Uses of 120068-37-3 differently. You can refer to the following data:
1. antifungal
2. Pesticide.
3. A broad spectrum insecticide which actively disrupts the CNS of contacted insects by blocking the passage of chloride ions through GABA receptors.
4. Fipronil is used for the control of a wide range of insect species in rice, cereals, corn, cotton, top fruit, sugar beet, sugar cane, oilseed rape, many vegetables and other high-value crops. It also has a veterinary use as an ectoparasiticide.

Agricultural Uses

Insecticide, Veterinary medicine: Not approved for use in EU countries. Fipronil was introduced into the U.S. in 1996 for use in animal health and indoor pest control. It is the constituent of many products for controlling a wide spectrum of domestic animal and residential pests.

Trade name

BES? 602; CEASEFIRE?; CHIPCO?; COMBAT?; FRONTLINE; MB-46030?; H&G?; ICON?; MAXFORCE? ANT STATION; MAXFORCE? ROACH STATION; REGENCY SOFION?; REGENT?; REGENT? 500-FS; TERMIDOR? L VI-NIL

Pharmacology

Fipronil is a phenylpyrazole, the mode of action of which is to inhibit nerve transmission in arthropods by blocking γ -aminobutyric acid-gated chloride channels. Fipronil is available as spray and spot-on formulations to control fleas and ticks on cats and dogs. The adulticidal activity of fipronil accounts for the majority of its activity, although additional activity against flea eggs and larvae results from the presence of fipronil on hairs and debris shed into the environment from treated pets.Autohistoradiography studies (11) into the cutaneous distribution of 14C-fipronil in the cat and dog following spot-on administration demonstrated that radioactivity was restricted principally to the stratum corneum, the viable epidermis, and the pilosebaceous units. Following its slow release from sebaceous glands, fipronil migrates in the sebum covering the skin and hairs by passive diffusion and was shown to persist on hair for up to 2 months after treatment.

Potential Exposure

Pyrazole/phenylpyrazole/organofluor ine insecticide; veterinary medicine. Fipronil was intro duced into the United States in 1996 for use in animal health and indoor pest control. It is the constituent of many products for controlling a wide spectrum of domestic ani mal and residential pests. Banned for use in EU.

Metabolic pathway

Through the abiotic degradation of fipronil in aqueous solution and on the soil surface, 5-amino-3- carbamoyl-1-[2,6-dichloro-4-(trifluoromethyl)-phenyl]-4- [(trifluoromethyl)sulfinyl]pyrazole is the only hydrolysis product detected. Fipronil in acidic aqueous solution exposed under a xenon lamp degrades with the concomitant appearance of 5-amino-3-cyano-1-[2,6- dichloro-4-(trifluoromethyl)-phenyl]-4- (trifluoromethyl)pyrazole and 5-amino-3-cyano-1-[2,6- dichloro-4-(trifluoromethyl)phenyl]pyrazole-4-sulfonic acid. Under field conditions, when fipronil is applied in formulation, four metabolites which include one product resulting from reduction on the sulfur atom of fipronil are detected.

Shipping

UN2588 Pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN2902 Pesticide, liquid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Degradation

Fipronil is stable in water at pH 5 and 7 but is slowly hydrolysed at pH 9 (DT50 28 days) to the amide (2). It undergoes rapid aqueous photolysis with a DT50 of ﹤0.5 day. The major photodecomposition product in water and on soil surfaces is desulfinyl-fipronil(3) which is formed by extrusion of the SO group. A minor photoproduct in water, on soil and on plant surfaces is the sulfonic acid (4). The mechanisms of these reactions are discussed in a recent paper by Bobe et al. (1998).

Toxicity evaluation

Acute oral LD50 for rats: 100 mg/kg

Waste Disposal

It is the responsibility of chemical waste generators to determine the toxicity and physical properties and of a discarded chemical and to properly identify its classification and certification as a haz ardous waste and to determine the disposal method. United States Environmental Protection Agency guidelines for the classification determination are listed in 40 CFR Parts 261.3. Additionally, waste generators must consult and fol low all regional, national, state and local hazardous waste laws to ensure complete and accurate classification and dis posal methods.

Check Digit Verification of cas no

The CAS Registry Mumber 120068-37-3 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 8 respectively; the second part has 2 digits, 3 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 120068-37:
(8*1)+(7*2)+(6*0)+(5*0)+(4*6)+(3*8)+(2*3)+(1*7)=83
83 % 10 = 3
So 120068-37-3 is a valid CAS Registry Number.
InChI:InChI=1/C12H4Cl2F6N4OS/c13-5-1-4(11(15,16)17)2-6(14)8(5)24-10(22)9(7(3-21)23-24)26(25)12(18,19)20/h1-2H,22H2

120068-37-3SDS

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

1.2 Other means of identification

Product number -
Other names 5-amino-1-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)-4-[(trifluoromethyl)sulfinyl]pyrazole-3-carbonitrile

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:120068-37-3 SDS

120068-37-3Synthetic route

trifluoromethylsulfinyl chloride
20621-29-8

trifluoromethylsulfinyl 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

fipronil
120068-37-3

fipronil

Conditions
ConditionsYield
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%
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;
trifluoromethylsulfinyl chloride
20621-29-8

trifluoromethylsulfinyl chloride

dimethylamine p-toluenesulfonate
2840-22-4

dimethylamine p-toluenesulfonate

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

fipronil
120068-37-3

fipronil

Conditions
ConditionsYield
In water; toluene88%
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

fipronil
120068-37-3

fipronil

Conditions
ConditionsYield
With trichlorophosphate; dimethylamine p-toluenesulfonate at 40℃; for 14h; Product distribution / selectivity;80.2%
With thionyl chloride; dimethylamine p-toluenesulfonate at 40℃; for 10h; Product distribution / selectivity;74.8%
Stage #1: Langlois reagent With thionyl chloride; dimethylamine p-toluenesulfonate In toluene at 0 - 5℃; for 0.5h;
Stage #2: 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole In toluene at 5 - 50℃; for 6.08333h; Product distribution / selectivity;
73%
potassium triflinate
41804-89-1

potassium triflinate

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

fipronil
120068-37-3

fipronil

Conditions
ConditionsYield
Stage #1: potassium triflinate With thionyl chloride; triethylamine hydrochloride In toluene at 0 - 5℃; for 0.5 - 0.833333h;
Stage #2: 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole In toluene at 5 - 35℃; for 11.75h; Product distribution / selectivity;
66%
Stage #1: potassium triflinate With thionyl chloride; pyridine hydrochloride In toluene at 0 - 5℃; for 0.833333h;
Stage #2: 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole In toluene at 5 - 35℃; for 11.75h; Product distribution / selectivity;
Stage #1: potassium triflinate With thionyl chloride; trimethylamine hydrochloride In toluene at 0 - 5℃; for 0.833333h;
Stage #2: 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole In toluene at 5 - 35℃; for 11.75h; Product distribution / selectivity;
5-amino-4-trifluoromethylsulfinyl-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-thiocarbamoylpyrazole
208652-17-9

5-amino-4-trifluoromethylsulfinyl-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-thiocarbamoylpyrazole

fipronil
120068-37-3

fipronil

Conditions
ConditionsYield
With hydrogenchloride In water; acetonitrile Product distribution / selectivity;
In water; acetonitrile Product distribution / selectivity; fluorescent light;
In water; acetonitrile at 65℃; Product distribution / selectivity;
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-3-bromo-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylthiopyrazole
120067-94-9

5-amino-3-bromo-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylthiopyrazole

A

5-amino-3-bromo-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulphinylpyrazole
120068-43-1

5-amino-3-bromo-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulphinylpyrazole

B

fipronil
120068-37-3

fipronil

trifluoromethanesulfinic acid
34642-42-7

trifluoromethanesulfinic acid

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

fipronil
120068-37-3

fipronil

Conditions
ConditionsYield
Stage #1: trifluoromethanesulfinic acid With thionyl chloride; triethylamine In toluene at 0 - 5℃; for 0.5h;
Stage #2: 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole; triethylamine hydrochloride In toluene at 50℃; for 6h; Product distribution / selectivity;
With thionyl chloride; N,N-dimethylisopropyl amine; potassium chloride; isopropyl-dimethyl-amine; hydrochloride In ethylbenzene at 0 - 35℃; for 11.75h; Inert atmosphere;
2,6-dichloro-4-(trifluoromethyl)aniline
24279-39-8

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

fipronil
120068-37-3

fipronil

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: nitrosylsulfuric acid; acetic acid / 30 - 55 °C
1.2: 0 - 15 °C
2.1: dichloromethane
3.1: boric acid; trichloroacetic acid; dihydrogen peroxide / chlorobenzene; water / 20 h / 15 - 20 °C
View Scheme
1,2-dichloro-4-(trifluoromethyl)benzene
328-84-7

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

fipronil
120068-37-3

fipronil

Conditions
ConditionsYield
Multi-step reaction with 5 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
5.1: boric acid; trichloroacetic acid; dihydrogen peroxide / chlorobenzene; water / 20 h / 15 - 20 °C
View Scheme
Multi-step reaction with 5 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
5.1: boric acid; trichloroacetic acid; dihydrogen peroxide / chlorobenzene; water / 20 h / 15 - 20 °C
View Scheme
2-chloro-4-(trifluoromethyl)aniline
39885-50-2

2-chloro-4-(trifluoromethyl)aniline

fipronil
120068-37-3

fipronil

Conditions
ConditionsYield
Multi-step reaction with 4 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
4.1: boric acid; trichloroacetic acid; dihydrogen peroxide / chlorobenzene; water / 20 h / 15 - 20 °C
View Scheme
dihydrogen peroxide
7722-84-1

dihydrogen peroxide

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 hydrogenchloride; sodium tungstate In water; 1,2-dichloro-ethane at 2 - 8℃; Large scale;
orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

fipronil
120068-37-3

fipronil

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

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

Conditions
ConditionsYield
99%
99%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

fipronil
120068-37-3

fipronil

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

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

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene at 200℃; for 3h; Temperature; Time; Molecular sieve; High pressure; Sonication; Autoclave; Sealed tube;98.9%
n-Butyl chloride
109-69-3

n-Butyl chloride

fipronil
120068-37-3

fipronil

N-5-butylamino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfinyl-1H-pyrazole

N-5-butylamino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfinyl-1H-pyrazole

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 80℃; for 8h; Sonication;96.7%
4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

fipronil
120068-37-3

fipronil

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

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

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene at 200℃; for 3h; Temperature; Time; Molecular sieve; High pressure; Sonication; Autoclave; Sealed tube;96.5%
With toluene-4-sulfonic acid In chlorobenzene for 1h; Molecular sieve; Microwave irradiation; Sealed tube;73%
2-Nitrobenzenesulfonyl chloride
1694-92-4

2-Nitrobenzenesulfonyl chloride

fipronil
120068-37-3

fipronil

C18H7Cl2F6N5O5S2
1225373-70-5

C18H7Cl2F6N5O5S2

Conditions
ConditionsYield
With sodium hydride In ethyl acetate at 0 - 20℃;96%
With sodium hydride In ethyl acetate at 2 - 20℃; for 4h;79.3%
1,4-dibromo-butane
110-52-1

1,4-dibromo-butane

fipronil
120068-37-3

fipronil

N-bis(1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfinyl-1H-pyrazol-5ylamino)butyl

N-bis(1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfinyl-1H-pyrazol-5ylamino)butyl

Conditions
ConditionsYield
With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 3h; Sonication; Microwave irradiation; Heating;95.2%
1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(4-bromophenylsulfonylamino)-1H-pyrazole-3-carbonitrile
1014394-95-6

1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(4-bromophenylsulfonylamino)-1H-pyrazole-3-carbonitrile

fipronil
120068-37-3

fipronil

C18H7BrCl2F6N4O3S2
1225373-68-1

C18H7BrCl2F6N4O3S2

Conditions
ConditionsYield
With sodium hydride In ethyl acetate at 0 - 20℃;95%
benzaldehyde
100-52-7

benzaldehyde

fipronil
120068-37-3

fipronil

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

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

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene at 200℃; for 3h; Temperature; Time; Molecular sieve; High pressure; Sonication; Autoclave; Sealed tube;94.8%
With toluene-4-sulfonic acid In toluene for 1h; Reagent/catalyst; Molecular sieve; Microwave irradiation; Sealed tube;84%
5-bromo-2-thiophenesulfonyl chloride
55854-46-1

5-bromo-2-thiophenesulfonyl chloride

fipronil
120068-37-3

fipronil

C16H5BrCl2F6N4O3S3

C16H5BrCl2F6N4O3S3

Conditions
ConditionsYield
With sodium hydride In ethyl acetate at 0 - 20℃;93%
1-bromo-butane
109-65-9

1-bromo-butane

fipronil
120068-37-3

fipronil

N-5-butylamino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfinyl-1H-pyrazole

N-5-butylamino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfinyl-1H-pyrazole

Conditions
ConditionsYield
With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 3h; Time; Sonication; Microwave irradiation; Heating;92.6%
With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 1h;92.6%
4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

fipronil
120068-37-3

fipronil

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

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

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene at 200℃; for 3h; Temperature; Time; Molecular sieve; High pressure; Sonication; Autoclave; Sealed tube;92.6%
3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

fipronil
120068-37-3

fipronil

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

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

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene at 200℃; for 3h; Temperature; Time; Molecular sieve; High pressure; Sonication; Autoclave; Sealed tube;91.8%
ethyl bromoacetate
105-36-2

ethyl bromoacetate

fipronil
120068-37-3

fipronil

ethyl N-[3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)-phenyl]-4-[(trifluoromethyl)-sulfinyl]-1H-pyrazol-5-yl]-aminoacetate
1430089-22-7

ethyl N-[3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)-phenyl]-4-[(trifluoromethyl)-sulfinyl]-1H-pyrazol-5-yl]-aminoacetate

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 20℃; for 3h; Cooling with ice;91%
1,4-diphenyl-but-2-ene-1,4-dione
4070-75-1

1,4-diphenyl-but-2-ene-1,4-dione

fipronil
120068-37-3

fipronil

C28H15ClF6N4O3S

C28H15ClF6N4O3S

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 50℃;91%
ethoxyacetyl chloride
14077-58-8

ethoxyacetyl chloride

triethylamine
121-44-8

triethylamine

fipronil
120068-37-3

fipronil

triethylamine salt of 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfinyl-5-(ethoxyacetamido)pyrazole
379215-14-2

triethylamine salt of 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfinyl-5-(ethoxyacetamido)pyrazole

Conditions
ConditionsYield
In tetrahydrofuran at 60℃; for 1.5h;90%
benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

fipronil
120068-37-3

fipronil

C18H8Cl2F6N4O3S2
1225373-74-9

C18H8Cl2F6N4O3S2

Conditions
ConditionsYield
With sodium hydride In ethyl acetate at 0 - 20℃;90%
fipronil
120068-37-3

fipronil

1,4-dimethyl but-2-enedioate
23055-10-9

1,4-dimethyl but-2-enedioate

C18H11ClF6N4O5S

C18H11ClF6N4O5S

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 50℃;90%
1,4-bibromocyclohexane
35076-92-7

1,4-bibromocyclohexane

fipronil
120068-37-3

fipronil

N-bis(1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfinyl-1H-pyrazol-5-ylamino)cyclohexyl

N-bis(1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfinyl-1H-pyrazol-5-ylamino)cyclohexyl

Conditions
ConditionsYield
With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 3h; Sonication; Microwave irradiation; Heating;89.5%
1,4-bis(bromomethyl)benzene
623-24-5

1,4-bis(bromomethyl)benzene

fipronil
120068-37-3

fipronil

N-bis(1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfinyl-1H-pyrazol-5ylamino)benzyl

N-bis(1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfinyl-1H-pyrazol-5ylamino)benzyl

Conditions
ConditionsYield
With potassium hydroxide In toluene at 20℃; for 3h; Sonication; Microwave irradiation; Heating;89.3%
ortho-anisaldehyde
135-02-4

ortho-anisaldehyde

fipronil
120068-37-3

fipronil

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

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

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene at 200℃; for 3h; Temperature; Time; Molecular sieve; High pressure; Sonication; Autoclave; Sealed tube;88.7%
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

fipronil
120068-37-3

fipronil

C19H10Cl2F6N4O3S2
1225373-72-7

C19H10Cl2F6N4O3S2

Conditions
ConditionsYield
With sodium hydride In ethyl acetate at 0 - 20℃;88%
C7H12O7S

C7H12O7S

fipronil
120068-37-3

fipronil

C18H11ClF6N4O5S

C18H11ClF6N4O5S

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 50℃;88%
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

fipronil
120068-37-3

fipronil

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

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

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene at 200℃; for 3h; Temperature; Time; Molecular sieve; High pressure; Sonication; Autoclave; Sealed tube;87.4%
With toluene-4-sulfonic acid In 1,3,5-trimethyl-benzene for 1h; Molecular sieve; Microwave irradiation; Sealed tube;78%
α,α',α''-trichloromesitylene
17299-97-7

α,α',α''-trichloromesitylene

fipronil
120068-37-3

fipronil

N-1,3,5-tri(1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfinyl-1H-pyrazol-5ylamino)benzyl

N-1,3,5-tri(1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfinyl-1H-pyrazol-5ylamino)benzyl

Conditions
ConditionsYield
With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 3h; Sonication; Microwave irradiation; Heating;87.2%
ethoxyacetyl chloride
14077-58-8

ethoxyacetyl chloride

fipronil
120068-37-3

fipronil

potassium salt of 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfinyl-5-(ethoxyacetamido)pyrazole

potassium salt of 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfinyl-5-(ethoxyacetamido)pyrazole

Conditions
ConditionsYield
With potassium hydroxide In acetonitrile at -5℃; for 4h;87%
Stage #1: ethoxyacetyl chloride; fipronil With triethylamine In tetrahydrofuran at 30℃; for 5h;
Stage #2: With hydrogenchloride In tetrahydrofuran; dichloromethane; water pH=2;
Stage #3: With potassium carbonate In tetrahydrofuran; dichloromethane; water
65%
Dimethyl oxalate
553-90-2

Dimethyl oxalate

fipronil
120068-37-3

fipronil

N,N'-bis[3-cyano-4-trifluoromethylsulfinyl-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazolyl]ethanediamide

N,N'-bis[3-cyano-4-trifluoromethylsulfinyl-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazolyl]ethanediamide

Conditions
ConditionsYield
With sodium ethanolate In toluene at 120℃; for 12h; Temperature; Time;86.5%

120068-37-3Relevant articles and documents

Preparation method of trifluoromethyl sulfinyl chloride

-

Paragraph 0019; 0021-0022, (2021/07/24)

The invention relates to a preparation method of trifluoromethyl sulfinyl chloride. The preparation method does not need to use a toxic reagent, namely thiophosgene, does not need to be further oxidized, and has the advantages of simple production process and low cost. The trifluoromethyl sulfinyl chloride is prepared from bis(trifluoromethyl) disulfide, a chlorination reagent and an oxidizing agent in a solvent by a one-pot method, the weight ratio of the solvent to the bis(trifluoromethyl) disulfide is (1: 1)-(500: 1), the temperature of the chlorination reaction is -30 DEG C to 80 DEG C, and the temperature of the oxidation reaction is -30 DEG C to 30 DEG C. The preparation method has the advantages that the preparation of the trifluoromethyl sulfinyl chloride does not need to use a toxic reagent, namely thiophosgene, further oxidation is not needed, meanwhile, the production process is simple, the conversion rate is high, and the production cost is low.

A PROCESS FOR SYNTHESIS OF FIPRONIL

-

Page/Page column 9-15, (2020/10/09)

The present disclosure relates to a process for the synthesis of Fipronil which is a broad spectrum insecticide (I). The process of the present disclosure provides fipronil with a yield in the range of 75% to 90% and purity in the range of 95% to 97%. By the process of the present disclosure, the amount of sulfone impurity i.e., 5-amino- 1 -(2, 6-dichloro-4-trifluoromethylphenyl)-3-cyano- 4-trifluoro methylsulfonyl pyrazole in fipronil observed is in the range of 0 % to 0.5 %.

Synthetic method of fipronil and analogues thereof

-

Paragraph 0040-0066, (2019/10/04)

The invention discloses a method for synthesizing fipronil and analogues thereof. The fipronil and analogues thereof are shown as a formula (I). The synthesis method comprises the following steps: (a) mixing a thioether compound shown as a formula (II) with trichloroacetic acid and an aprotic organic solvent; (b) adding hydrogen peroxide into the mixture obtained in the step (a), and carrying out oxidation reaction, so as to obtain fipronil as shown in a formula (I) and analogues thereof; the substituents in the formula (I) and the formula (II) are defined in the specification. The novel synthetic method is simple in condition and easy for industrial production.

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