Fipronil sulfone

Base Information

• Chemical Name: Fipronil sulfone
• CAS No.: 120068-36-2
• Molecular Formula: C12H4 Cl2 F6 N4 O2 S
• Molecular Weight: 453.152
• European Community (EC) Number: 690-359-5
• UNII: KE7T0T1PQ7
• DSSTox Substance ID: DTXSID6074750
• Nikkaji Number: J1.048.279H
• Wikidata: Q27156870
• Mol file: 120068-36-2.mol

Synonyms:fipronil sulfone;fipronil sulphone

Chemical Property of Fipronil sulfone

Chemical Property:

• Vapor Pressure: 2.2E-11mmHg at 25°C
• Melting Point: 225℃
• Boiling Point: 531.6°Cat760mmHg
• PKA: -8.12±0.20(Predicted)
• Flash Point: 275.3°C
• PSA: 110.15000
• Density: 1.85g/cm³
• LogP: 5.60728
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 2
• Exact Mass: 451.9336209
• Heavy Atom Count: 27
• Complexity: 706

Purity/Quality:

99% ^*data from raw suppliers

Fipronil sulfone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T,N
• Statements: 25-50
• Safety Statements: 45-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=C(C(=C1Cl)N2C(=C(C(=N2)C#N)S(=O)(=O)C(F)(F)F)N)Cl)C(F)(F)F
• Uses: Fipronil Sulfone is a sulfone metabolite of the insecticide Fipronil (F342200). Fipronil Sulfone blocks γ-aminobutyric acid- and glutamate-activated chloride channels in mammalian and insect neurons.

Technology Process of Fipronil sulfone

There total 6 articles about Fipronil sulfone 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: 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

Reference yield:

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

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In chloroform; water;

Reference yield:

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

Guidance literature:

With potassium permanganate; magnesium sulfate; In water; acetone; at 20 ℃;

DOI:10.1021/tx980157t

upstream raw materials:

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

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

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

fipronil

Downstream raw materials:

1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-[(2-hydroxy-ethyl)(methyl)amino]-4-[(trifluoromethyl)sulfonyl]-1H-pyrazole-3-carbonitrile

5-bromo-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethanesulphonylpyrazole

5-amino-1-(2-chloro-6-dimethylamino-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfonylpyrazole

5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-iodo-4-methanesulphonylpyrazole

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF FIPRONIL AND ANALOGUES THEREOF". Page/Page column 29-30. . Retrieved 2009/07/18.
• 2、 -. "Antiparasitical agents and methods for treating, preventing and controlling external parasites in animals". Page/Page column 27. . Retrieved 2008/06/13.