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122454-29-9

122454-29-9 Structure

122454-29-9 Structure
IdentificationBack Directory
[Name]

4-Bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile
[CAS]

122454-29-9
[Synonyms]

Tralopyril
N-Deethoxymethyl Chlorfenapyr
4-broMo-2-(4-chlorophenyl)-5-(trifluoroMethyl)-3H-pyrrole-3-carbonitrile
4-bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitri le
1H-Pyrrole-3-carbonitrile, 4-bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-
[Molecular Formula]

C12H5BrClF3N2
[MDL Number]

MFCD13184274
[MOL File]

122454-29-9.mol
[Molecular Weight]

349.53
Questions And AnswerBack Directory
[Description]

Tralopyril (TP) is a biocide that has recently been introduced into marine antifouling paints, applied to boat hulls or static structures such as oil rig and drilling platform legs, which are submerged under water.
[preparation]

Tralopyril is an important intermediate in the synthesis of carbofuran, and bromine is the core raw material for the synthesis of Tralopyril. Tralopyril is a pyrrole resulting from the N-dealkylation of the ethoxymethyl group of chlorfenapyr. Chlorfenapyr is the first commercial proinsecticide developed by introducing ethoxymethyl group into the pyrrole N of tralopyril.
Chemical PropertiesBack Directory
[Boiling point ]

450.6±45.0 °C(Predicted)
[density ]

1.78±0.1 g/cm3(Predicted)
[pka]

10.24±0.50(Predicted)
[Henry's Law Constant]

4.5×103 mol/(m3Pa) at 25℃, Ebert et al. (2023)
[InChI]

InChI=1S/C12H5BrClF3N2/c13-9-8(5-18)10(19-11(9)12(15,16)17)6-1-3-7(14)4-2-6/h1-4,19H
[InChIKey]

XNFIRYXKTXAHAC-UHFFFAOYSA-N
[SMILES]

N1C(C(F)(F)F)=C(Br)C(C#N)=C1C1=CC=C(Cl)C=C1
[EPA Substance Registry System]

4-Bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile (122454-29-9)
Safety DataBack Directory
[Symbol(GHS) ]

Environment (GHS09)
GHS09
[Signal word ]

Warning
[Hazard statements ]

H410
[Precautionary statements ]

P273-P391-P501
[Hazard Codes ]

N
[Risk Statements ]

50/53
[Safety Statements ]

60-61
Hazard InformationBack Directory
[Uses]

N-Deethoxymethyl Chlorfenapyr is a primary metabolite of Chlorfenapyr (C428500). Chlorfenapyr is a halogenated pyrrole based pro-insecticide. Chlorfenapyr functions by metabolizing into an active insecticide after entering the host. Chlorfenapyr is used primarily as a means of pest control on cotton.
[Application]

Tralopyril was developed as a marine antifouling agent for use in antifouling coatings. The compound has been registered with the US EPA since 2007. Since then, a range of marine coatings have been developed utilizing tralopyril for control of barnacles and other invertebrate animal fouling organisms, frequently, but not exclusively, in combination with a soft fouling control agent. 
[Definition]

ChEBI: Tralopyril is a pyrrole resulting from the N-dealkylation of the ethoxymethyl group of chlorfenapyr. It is the active insecticide of the proinsecticide chlorfenapyr. It has a role as an acaricide, an insecticide and an antifouling biocide. It is an organochlorine acaricide, an organochlorine insecticide, an organofluorine acaricide, an organofluorine insecticide, a member of pyrroles, a nitrile, a member of monochlorobenzenes and an organobromine compound.
[Mechanism of action]

Acts by disrupting mitochondrial function, leading to energy depletion and cell death in target pests
[Synthesis]

Tralopyril is a pyrrole resulting from the N-dealkylation of the ethoxymethyl group of chlorfenapyr.
[Pesticide Type]

Insecticide; Acaricide; Molluscicide; Metabolite
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