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

• ChemBase ID: 168985
• Molecular Formular: C12H4Cl2F6N4O2S
• Molecular Mass: 453.1471792
• Monoisotopic Mass: 451.93362107
• SMILES: c1(c(c(n(n1)c1c(cc(cc1Cl)C(F)(F)F)Cl)N)S(=O)(=O)C(F)(F)F)C#N
• Canonical SMILES: N#Cc1nn(c(c1S(=O)(=O)C(F)(F)F)N)c1c(Cl)cc(cc1Cl)C(F)(F)F
• InChI: InChI=1S/C12H4Cl2F6N4O2S/c13-5-1-4(11(15,16)17)2-6(14)8(5)24-10(22)9(7(3-21)23-24)27(25,26)12(18,19)20/h1-2H,22H2
• InChIKey: LGHZJDKSVUTELU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-trifluoromethanesulfonyl-1H-pyrazole-3-carbonitrile
• IUPAC Traditional name: 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-trifluoromethanesulfonylpyrazole-3-carbonitrile
• Synonyms: 5-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfonylpyrazole; 5-Amino-1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfonyl)pyrazole-3-carbonitrile; MB 46136; Fipronil Sulfone

Database IDs

• CAS Number: 120068-36-2
• PubChem SID: 162263117
• PubChem CID: 3078139

CALCULATED PROPERTIES

• Acid pKa: 19.364098
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 4.596032
• LogD (pH = 7.4): 4.596033
• Log P: 4.596033
• Molar Refractivity: 83.1399 cm^3
• Polarizability: 31.496307 Å^3
• Polar Surface Area: 101.77 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F342215

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.

REFERENCES

• Zhao, X. et al.: J. Pharmacol. Exp. Therap., 314, 363 (2005)
• Mulrooney, J.E. et al.: J. Econ. Entomol., 92, 1364 (2005)
• Hainzl, D. et al.: Chem. Res. Toxicol., 11, 1529 (2005)