CAS 122454-29-9 Tralopyril (HCID 183559)

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Basic information

CAS: 122454-29-9
Standard SMILES: N#Cc1c(-c2ccc(Cl)cc2)[nH]c(C(F)(F)F)c1Br
InChIKey: XNFIRYXKTXAHAC-UHFFFAOYSA-N
Molecular formula: C12H5BrClF3N2
Average molar mass: 349.53 g/mol
Monoisotopic mass: 347.9276726

Overview

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 a nitrile, an organochlorine insecticide, a member of pyrroles, an organobromine compound, an organochlorine acaricide, an organofluorine insecticide, an organofluorine acaricide and a member of monochlorobenzenes.

Names & identifiers

Preferred name: Tralopyril
IUPAC: 4-bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile
English name: Tralopyril
Molecular formula: C12H5BrClF3N2
Molecular weight: 349.53

Names & synonyms

Tralopyril122454-29-94-bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrileEconea1H-Pyrrole-3-carbonitrile, 4-bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-DTXSID6041503MEC6MCY7QB4-Bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrileAC-303268DTXCID4021503CHEBI:1414974-bromo-2-(p-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile

Show more names

ralopyril4-Bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-...TralopyhrilBromopyrrolic nitrileTralopyril (Standard)Hexazinone Impurity 20? Bromopyrrolidone (Tralopyril)

CL-303268RefChem:190553602-784-5Tralopyril [ISO]MFCD13184274N-Deethoxymethyl Chlorfenapyr1H-Pyrrole-3-carbonitrile,4-bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-UNII-MEC6MCY7QB

Database identifiers

Properties

Computed structural properties

XLogP: 4.3
Topological polar surface area: 39.6 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 4
Rotatable bonds: 1
Heavy atoms: 19
Formal charge: 0
Complexity: 373

Experimental & physicochemical properties

Collision Cross Section157.9 Å² [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID6041503]

Physicochemical properties

Boiling point: 450.6 · 450.6±45.0 °C(Predicted)
Density: 1.78 · 1.78±0.1 g/cm3(Predicted)
pka: 10.24 · 10.24±0.50(Predicted)
Henry's Law Constant: 4.5 · 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
FDA UNII: 6 MCY7QB · MEC6MCY7QB
EPA Substance Registry System: 4 · 4-Bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile (122454-29-9)
Symbol(GHS): 9 · GHS09

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 5.7% (5 of 87) of reports.

Danger

H300 (21.8%): Fatal if swallowed [Danger Acute toxicity, oral]

P260, P261, P262, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P316, P319, P320, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 87 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

Hazard information

Regulatory Information1H-Pyrrole-3-carbonitrile, 4-bromo-2-(4-chlorophenyl)-5-: HSNO Approval: HSR006716 Approved with controls

Hazard Classes and Categories · 2 items

Acute Tox. 2 (21.8%)

Hazardous to the aquatic environment (Acute) - Category 1

Safety data

risk_code: 50/53
Signal word: Warning
Symbol(GHS): GHS09
hazard_code: N
safety_code: 60-61
Hazard statements: H410
Precautionary statements: P273-P391-P501

Chemistry & industry

Applications · 2 items

DescriptionTralopyril (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.

UsesN-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.