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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.
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile
fipronil
| Conditions | Yield |
|---|---|
|
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;
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% |
|
With
dihydrogen peroxide;
In
dichloro-acetic acid; water; trichloroacetic acid;
at 20 ℃;
for 1h;
|
95% |
|
With
dihydrogen peroxide;
In
dichloromethane; water; trichloroacetic acid;
at 20 ℃;
for 3h;
Product distribution / selectivity;
|
93.8% |
|
With
dihydrogen peroxide;
In
dichloromethane; water; trichloroacetic acid;
at 20 ℃;
for 2h;
|
93.8% |
|
With
sodium bromate; ammonium cerium(IV) nitrate;
In
dichloromethane; water;
for 0.583333h;
Product distribution / selectivity;
Silica gel;
|
90% |
|
With
dihydrogen peroxide;
chloroauric acid;
In
methanol; water;
at 20 ℃;
for 1h;
Product distribution / selectivity;
|
90% |
|
With
1,1-dihydroperoxycyclohexane;
In
dichloromethane;
for 1h;
Product distribution / selectivity;
|
90% |
|
With
dihydrogen peroxide; trifluoroacetic acid;
In
toluene;
at 20 ℃;
for 10h;
Solvent;
|
90% |
|
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile;
With
trifluoromethylsulfonic anhydride; dihydrogen peroxide;
In
ethanol; water;
at 18 - 22 ℃;
for 0.333333h;
With
Oxone;
at -15 ℃;
Product distribution / selectivity;
|
86% |
|
With
dibenzoyl peroxide;
In
dichloromethane;
at 20 ℃;
for 2h;
Concentration;
|
82% |
|
With
dihydrogen peroxide;
In
dibromoacetic acid; water; chlorobenzene;
at 15 - 17 ℃;
Product distribution / selectivity;
|
55.5% |
|
With
dihydrogen peroxide; trifluoroacetic acid;
In
chlorobenzene;
at 0 - 20 ℃;
Product distribution / selectivity;
Silica gel;
|
95 %Chromat. |
|
With
dihydrogen peroxide; trifluoroacetic acid;
zinc(II) oxide;
In
water;
at 10 - 12 ℃;
for 4h;
Product distribution / selectivity;
|
|
|
With
dichloro-acetic acid; dihydrogen peroxide; boric acid; trichloroacetic acid;
In
water;
at 15 - 20 ℃;
for 20h;
|
|
|
With
dihydrogen peroxide;
dichloro-acetic acid;
at 20 ℃;
Product distribution / selectivity;
|
|
|
With
dihydrogen peroxide;
In
dichloro-acetic acid; water;
at 20 ℃;
Product distribution / selectivity;
|
|
|
With
sulfuric acid; dihydrogen peroxide;
In
1,2-dichloro-ethane;
at 5 - 13 ℃;
Product distribution / selectivity;
|
|
|
With
dihydrogen peroxide; boric acid; trichloroacetic acid;
In
water; chlorobenzene;
at 15 - 20 ℃;
for 20h;
Reagent/catalyst;
Concentration;
Time;
Temperature;
|
371 g |
|
With
sulfuric acid; dihydrogen peroxide;
In
water; 1,2-dichloro-ethane;
at 5 - 15 ℃;
Temperature;
|
358 g |
|
With
hydrogenchloride; sodium tungstate; dihydrogen peroxide;
In
1,2-dichloro-ethane;
at 2 - 8 ℃;
Large scale;
|
505 kg |
trifluoromethylsulfinyl chloride
5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole
fipronil
| 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% |
|
With
p-toluenesulfonic acid dimethylamine salt;
In
chloroform;
at 50 ℃;
Inert atmosphere;
|
88% |
|
With
diethyl amine hydrochloride; boric acid; calcium chloride;
In
1,2-dichloro-ethane;
at 50 ℃;
for 5h;
Reagent/catalyst;
Temperature;
Green chemistry;
|
87% |
|
5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole;
With
dimethylamine p-toluenesulfonate; sodium sulfate; trichlorophosphate;
In
chloroform;
at 20 ℃;
for 0.5h;
trifluoromethylsulfinyl chloride;
In
chloroform;
at 0 ℃;
for 5h;
Solvent;
Reagent/catalyst;
Reflux;
|
81% |
|
pyridine hydrochloride;
In
toluene;
at 0 - 35 ℃;
for 11.75h;
Product distribution / selectivity;
|
|
|
trimethylamine hydrochloride;
In
toluene;
at 0 - 35 ℃;
for 11.75h;
Product distribution / selectivity;
|
The CAS number of Fipronil is 120068-37-3.
More information of Fipronil 120068-37-3 are:
|
CAS Number |
120068-37-3 |
|
Density |
1.87 g/cm3 |
|
Melting Point |
200-201 ºC |
|
Boiling Point |
510.1 ºC at 760 mmHg |
|
Flash Point |
262.3 ºC |
|
Vapor Pressure |
1.61E-10mmHg at 25°C |
|
Refractive Index |
1.617 |
|
HS CODE |
29331990 |
|
PSA |
103.91000 |
|
LogP |
5.72608 |
|
Pka |
-5.86±0.20(Predicted) |
Synonyms for Fipronil 120068-37-3:5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfinyl)pyrazole-3-carbonitrile;MB 46030;RM 1601;Fipronil (JAN);1H-Pyrazole-3-carbonitrile, 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-;Fluocyanobenpyrazole;Fipronil 95%TC;
The chemical formula of Fipronil is C12H4Cl2F6N4OS which containing 12 Carbon atoms,4 Hydrogen atoms,2 Chlorine atoms,6 Fluorine atoms,4 Nitrogen atoms,1 Oxygen atoms and 1 Sulfur atoms,and the molecular weight of Fipronil is 437.152.
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.
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
Relevant articles related to Fipronil:
|
Article |
Source |
|
Method for preparing fipronil (by machine translation) |
- Paragraph 0015-0021, (2020/04/22) |
|
A PROCESS FOR SYNTHESIS OF FIPRONIL |
- Page/Page column 9-15, (2020/10/09) |
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