Fipronil-sulfide

Base Information

• Chemical Name: Fipronil-sulfide
• CAS No.: 120067-83-6
• Molecular Formula: C12H4 Cl2 F6 N4 S
• Molecular Weight: 421.153
• European Community (EC) Number: 601-662-9
• DSSTox Substance ID: DTXSID50869644
• Nikkaji Number: J514.721B
• Wikidata: Q27156871
• Mol file: 120067-83-6.mol

Synonyms:fipronil-sulfide;Fipronil Sulfide;120067-83-6;5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfanyl)pyrazole-3-carbonitrile;Fipronil-sulfide 10 microg/mL in Acetonitrile;Fipronil-sulfide 100 microg/mL in Acetonitrile;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;5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)thio]pyrazole-3-carbonitrile;MB 45950;SCHEMBL15406;CHEBI:83488;DTXSID50869644;AKOS015908768;Fipronil-sulfide 1000 microg/mL in Acetone;FT-0668542;NS00000351;Fipronil sulfide, PESTANAL(R), analytical standard;Q27156871;4-trifluoromethylthio-3-cyano-5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole;5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylthiopyrazole;5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)3-cyano-4-trifluoromethylthiopyrazole;5-amino-3-cyano-1-(2,6-dichloro-4-trifluoro methyl-phenyl)-4-trifluoromethylthio pyrazole;5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethyl- phenyl)-4-trifluoromethylthiopyrazole;5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylthiopyrazole;5-amino-3-cyano-1-(2,6-dichloro-4-trifluromethylphenyl)-4-trifluromethylthio pyrazole;5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfanyl]-1H-pyrazole-3-carbonitrile

Chemical Property of Fipronil-sulfide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 161-163 °C(Solv: toluene (108-88-3))
• Refractive Index: 1.592
• Boiling Point: 393.242oC at 760 mmHg
• PKA: -4.16±0.20(Predicted)
• Flash Point: 191.626oC
• PSA: 92.93000
• Density: 1.761g/cm3
• LogP: 5.84488
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 2
• Exact Mass: 419.9437917
• Heavy Atom Count: 25
• Complexity: 526

Purity/Quality:

99.9% ^*data from raw suppliers

FipronilSulfide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=C(C(=C1Cl)N2C(=C(C(=N2)C#N)SC(F)(F)F)N)Cl)C(F)(F)F
• Uses: Fipronil Sulfide is a degradation product of the insecticide Fipronil (F342200).

Technology Process of Fipronil-sulfide

There total 17 articles about Fipronil-sulfide 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%

Langlois reagent (2926-29-6) + 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (120068-79-3) → 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile (120067-83-6)

Guidance literature:

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;

With phosphorus trichloride; In toluene; at 50 ℃; for 5h; Temperature;

Reference yield: 90.8%

5-amino-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-4-thiocyanato-1H-pyrazole-3-carbonitrile (120069-10-5) + Bromotrifluoromethane (75-63-8) → 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile (120067-83-6)

Guidance literature:

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;

Bromotrifluoromethane; In DMF (N,N-dimethyl-formamide); at 20 - 45 ℃; for 1.5h; under 8625.86 Torr; Product distribution / selectivity;

Reference yield: 85.0%

Bromotrifluoromethane (75-63-8) + 4,4'-dithiobis [5-amino-3-cyano-1-{2,6-dichloro-4-(trifluoromethyl)phenyl}-1H-pyrazole] (130755-46-3) → 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile (120067-83-6)

Guidance literature:

With sulfur dioxide; sodium formate; In N,N-dimethyl-formamide; at 60 ℃; for 4h; under 9000.7 - 9750.8 Torr; Mechanism; Product distribution; other reagent, other perhalogenoalkanes, other disulfide;

upstream raw materials:

Bromotrifluoromethane

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

Trifluoromethylsulfenyl chloride

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

Downstream raw materials:

fipronil

fipronil sulfone

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

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

Refernces

• 1、 Hainzl, Dominik,Cole, Loretta M.,Casida, John E.. "Mechanisms for selective toxicity of fipronil insecticide and its sulfone metabolite and desulfinyl photoproduct". . p. 1529 - 1535. Retrieved 1998.
• 2、 Paolini, Léa,Hausser, Nicolas,Zhang, Tong. "Chiral resolution of the insecticide fipronil enantiomers and the simultaneous determination of its major transformation products by high-performance liquid chromatography interfaced with mass spectrometry". supporting information. p. 473 - 483. Retrieved 2022/01/22.
• 3、 -. "Preparation method of 5-amino-1-(2,6-dihydro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylmercapto)-1H-parazole-3-nitrile". Paragraph 0028; 0029. . Retrieved 2016/12/07.