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

• ChemBase ID: 127424
• Molecular Formular: C12H4Cl2F6N4OS
• Molecular Mass: 437.1477792
• Monoisotopic Mass: 435.93870645
• SMILES: FC(F)(F)S(=O)c1c(C#N)nn(c2c(Cl)cc(cc2Cl)C(F)(F)F)c1N
• Canonical SMILES: N#Cc1nn(c(c1S(=O)C(F)(F)F)N)c1c(Cl)cc(cc1Cl)C(F)(F)F
• InChI: InChI=1S/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
• InChIKey: ZOCSXAVNDGMNBV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-trifluoromethanesulfinyl-1H-pyrazole-3-carbonitrile
• IUPAC Traditional name: fipronil
• Synonyms: 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile; (+/-)-Fipronil; 1-(2,6-Dichloro-4-trifluoromethylphenyl)-3-cyano-5-amino-4-(trifluoromethylsulfinyl)pyrazole; Frontline Spot-on; Frontline Spray; Frontline Top Spot; Goliath gel; Granedo MC; Grenade MC; Maxforce FC; Maxforce FC Select Roach Killer Bait Gel; Over'n Out; Regent; Regent TS; Termidor 80WG; TopChoice; Fipronil; Fluocyanobenpyrazole; Termidor; Fipronil; Fipronil; 氟虫腈/锐劲特

Database IDs

• CAS Number: 120068-37-3
• EC Number: 424-610-5
• MDL Number: MFCD00867812
• Beilstein Number: 8090115
• PubChem SID: 162221745; 24870190
• PubChem CID: 3352
• CHEBI ID: 5063
• ATC CODE: QP53AX15
• CHEMBL: 101326
• Chemspider ID: 3235
• KEGG ID: D01042
• Unique Ingredient Identifier: QGH063955F
• Wikipedia Title: Fipronil

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 4.4891367
• LogD (pH = 7.4): 4.489139
• Log P: 4.489139
• Molar Refractivity: 83.6635 cm^3
• Polarizability: 30.806074 Å^3
• Polar Surface Area: 84.7 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White SOlid
• Melting Point: 196-201 °C; 200.5 °C; 202-204°C
• Density: 1.477-1.626 g/cm3

Safety Information

• Storage Condition: Refrigerator
• RTECS: UQ4430250
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 23/24/25-48/25-50/53
• Safety Statements: 28-36/37-45-60-61
• GHS Pictograms: GHS06; GHS08; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H331-H372-H410
• GHS Precautionary statements: P261-P273-P280-P301 + P310-P311-P501
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

Product Information

• Grade: PESTANAL®, analytical standard
• Empirical Formula (Hill Notation): C12H4Cl2F6N4OS

DETAILS

Sigma Aldrich - 46451

Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH

Toronto Research Chemicals - F342200

A broad spectrum insecticide which actively disrupts the CNS of contacted insects by blocking the passage of chloride ions through GABA receptors.

REFERENCES

• Ling, S., et al.: App. Entomol. Zool., 44, 543 (2009)
• Li, X., et al.: Environ. Toxicol. Chem., 29, 127 (2009)
• Savant, R., et al.: J. Agric. Food Chem., 58, 1447 (2009)