Fipronil

Base Information

• Chemical Name: Fipronil
• CAS No.: 120068-37-3
• Molecular Formula: C12H4Cl2F6N4OS
• Molecular Weight: 437.152
• Hs Code.: 29331990
• European Community (EC) Number: 424-610-5,601-663-4
• ICSC Number: 1503
• NSC Number: 758960
• UNII: QGH063955F
• DSSTox Substance ID: DTXSID4034609
• Nikkaji Number: J562.376F
• Wikipedia: Fipronil
• Wikidata: Q415933
• NCI Thesaurus Code: C74341
• Pharos Ligand ID: CZCBGBLM1734
• Metabolomics Workbench ID: 53175
• ChEMBL ID: CHEMBL101326
• Mol file: 120068-37-3.mol

Synonyms:5-amino-1-(2,6-dichloro-alpha,alpha,alpha-trifluoro-p-tolyl)-4-trifluoromethylsulfinylpyrazole-3-carbonitile;fipronil

Chemical Property of Fipronil

Chemical Property:

• Appearance/Colour: clear colorless or slightly yellow liquid
• Vapor Pressure: 1.61E-10mmHg at 25°C
• Melting Point: 200-201 ºC
• Refractive Index: 1.617
• Boiling Point: 510.1 ºC at 760 mmHg
• PKA: -5.86±0.20(Predicted)
• Flash Point: 262.3 ºC
• PSA: 103.91000
• Density: 1.87 g/cm³
• LogP: 5.72608
• Storage Temp.: 0-6°C
• Water Solubility.: 1.9-2.4 mg 1l-1 (20 °C）
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 2
• Exact Mass: 435.9387063
• Heavy Atom Count: 26
• Complexity: 599

Purity/Quality:

≥95% ^*data from raw suppliers

Fipronil ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T,N
• Statements: 23/24/25-48/25-50/53-55-57-36
• Safety Statements: 26-36/37/39-45-60-61-36/37-28

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Other Insecticides
• Canonical SMILES: C1=C(C=C(C(=C1Cl)N2C(=C(C(=N2)C#N)S(=O)C(F)(F)F)N)Cl)C(F)(F)F
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed.
• Effects of Short Term Exposure: The substance may cause effects on the central nervous system. This may result in irritability and convulsions. The effects may be delayed.
• Effects of Long Term Exposure: The substance may have effects on the liver. This may result in tissue lesions.
• 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.
• Uses: antifungal Pesticide. A broad spectrum insecticide which actively disrupts the CNS of contacted insects by blocking the passage of chloride ions through GABA receptors. 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.

Technology Process of Fipronil

There total 16 articles about Fipronil which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

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

Guidance literature:

With dimethylamine p-toluenesulfonate; for 10h; Heating;

Reference yield: 98.0%

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile (120067-83-6) → fipronil (120068-37-3)

Guidance literature:

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;

Reference yield: 96.0%

5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile (120067-83-6) → fipronil (120068-37-3) + fipronil sulfone (120068-36-2)

Guidance literature:

With dihydrogen peroxide; trifluoroacetic acid; In dichloromethane; at 10 - 12 ℃; for 3h;

DOI:10.1016/j.jfluchem.2006.04.002

upstream raw materials:

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

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

sulfur dioxide

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

Downstream raw materials:

1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-5-(prop-2-yn-1-ylamino)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carbonitrile

N-(3-cyano-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfinyl)-1H-pyrazol-5-yl)acetamide

3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-iodo-4-trifluoromethylsulphinylpyrazole

1,4-dioxane

Refernces

• 1、 -. "Method for preparing fipronil (by machine translation)". Paragraph 0015-0021. . Retrieved 2020/04/22.
• 2、 -. "A PROCESS FOR SYNTHESIS OF FIPRONIL". Page/Page column 9-15. . Retrieved 2020/10/09.