122454-29-9

Basic information

• Product Name: 4-Bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile
• Synonyms: 1H-Pyrrole-3-carbonitrile, 4-bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-;4-bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitri le;Tralopyril;4-broMo-2-(4-chlorophenyl)-5-(trifluoroMethyl)-3H-pyrrole-3-carbonitrile;N-Deethoxymethyl Chlorfenapyr
• CAS NO: 122454-29-9
• Molecular Formula: C₁₂H₅BrClF₃N₂
• Molecular Weight: 349.53
• Product Categories: paint
• Mol File: 122454-29-9.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 450.6 ºC at 760 mmHg
• Flash Point: 226.3 ºC
• Appearance: Beige to slightly brown powder
• Density: 1.78 g/cm³
• Vapor Pressure: 2.61E-08mmHg at 25°C
• Refractive Index: 1.606
• PKA: 10.24±0.50(Predicted)
• CAS DataBase Reference: 4-Bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile(122454-29-9)
• EPA Substance Registry System: 4-Bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile(122454-29-9)

Safety Data

• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61
• Hazardous Substances Data: 122454-29-9(Hazardous Substances Data)

Usage

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.

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.

InChI:InChI=1/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

Upstream product

• 122454-23-3 2-(p-chlorophenyl)-5-(trifluoromethyl)-pyrrole-3-carbonitrile 
• 623-03-0 4-Cyanochlorobenzene 
• 122460-66-6 4-(p-chlorophenyl)-2-(trifluoromethyl)-1,3-oxazol-5-one 
• 6212-33-5 2-(4-Chlorophenyl)glycine 

Downstream Products

• 144032-68-8 N-((3-bromo-5-(4-chlorophenyl)-4-cyano-2-(trifluoromethyl)-1H-pyrrol-1-yl) methyl) acetamide 
• 890929-78-9 4-bromo-1-((2-chloroethoxy)methyl)-2-(4-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile 
• 122453-73-0 chlorfenapyr 
• 890929-81-4 4-bromo-1-((2-bromoethoxy)methyl)-2-(4-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile 
• 890929-80-3 4-bromo-2-(4-chlorophenyl)-1-((2-fluoroethoxy)methyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile 
• 890929-87-0 4-bromo-1-((3-chloropropoxy)methyl)-2-(4-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile 
• 890929-76-7 4-bromo-1-((chloromethoxy)methyl)-2-(4-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile 
• 890929-86-9 4-bromo-2-(4-chlorophenyl)-1-((2-(methylsulfonyl)ethoxy)methyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile 
• 890929-85-8 4-bromo-2-(4-chlorophenyl)-1-((2-(methylsulfinyl)ethoxy)methyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile 
• 1413929-73-3 benzyl 3-bromo-5-(4-chlorophenyl)-4-cyano-1H-pyrrole-2-carboxylate 

Relevant articles and documents

Preparation method of trobiglide

The present invention discloses a method of preparation of trilobiril, specifically related to the field of agricultural technology, the preparation method provided by the present invention comprises the following steps: step 1, p-chlorobenzonitrile disso

Application of 2-aryl substituted pyrrole compound in medicine for killing oncomelania hupensis

The invention relates to an application of 2-aryl substituted pyrrole compound in a medicine for killing oncomelania hupensis and belongs to the technical field of prevention and treatment of bilharziasis, and particularly provides the chemical structure of the 2-aryl substituted pyrrole compound and a preparation method of same. The 2-aryl substituted pyrrole compound, being an active component,is used for preparing the snail killing agent in the forms of suspending agents, emulsions and micro-emulsions for killing the oncomelania hupensis. Immersion killing use amount of the 2-aryl substituted pyrrole compound being the active component of the snail killing agent is 0.1-10.00 mg/l, and immersion killing time is 24-72 h. The use amount of spray application is 1-10 g/m and action timeis 3-7 days. Experiment proves that the 2-aryl substituted pyrrole compound has killing activity on the oncomelania hupensis and is lower than a snail killing agent, niclosamide, in the prior art in toxicity on aquatic organisms. The compound can be processed to prepare the snail killing agents and applied in the field of prevention and treatment of bilharziasis.

PRODUCTION OF ARYLPYRROL COMPOUNDS IN THE PRESENCE OF DIPEA BASE

The invention relates to a process for the production of compounds of formula (I), comprising Step A of reacting compounds of formula (II) with 2,3-dihalopropionitrile or 2-haloacrylonitrile in the presence of DIPEA. It also relates to a process for the production of compounds of formula (III), comprising Step B of reacting compounds of formula (I) with Br2 in the presence of DIPEA. It also relates to a process C for the production of compounds of formula (IV), comprising Step C of reacting compounds of formula (III) with di(C1-C4-alkoxy)methane and either POCl3, or a mixture comprising POCl3 and DMF, in the presence of DIPEA. It also relates to the use of DIPEA as a base in the production of compounds of formula (I), compounds of formula (III) or compounds of formula (IV).