Tralopyril

Base Information

• Chemical Name: Tralopyril
• CAS No.: 122454-29-9
• Molecular Formula: C12H5BrClF3N2
• Molecular Weight: 349.537
• European Community (EC) Number: 602-784-5
• UNII: MEC6MCY7QB
• DSSTox Substance ID: DTXSID6041503
• Nikkaji Number: J754.617C
• Wikidata: Q17326630
• Metabolomics Workbench ID: 143692
• ChEMBL ID: CHEMBL2253356
• Mol file: 122454-29-9.mol

Synonyms:4-bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile;tralopyril

Chemical Property of Tralopyril

Chemical Property:

• Appearance/Colour: Beige to slightly brown powder
• Vapor Pressure: 2.61E-08mmHg at 25°C
• Refractive Index: 1.606
• Boiling Point: 450.6 ºC at 760 mmHg
• PKA: 10.24±0.50(Predicted)
• Flash Point: 226.3 ºC
• PSA: 39.58000
• Density: 1.78 g/cm³
• LogP: 4.98808
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 347.92767
• Heavy Atom Count: 19
• Complexity: 373

Purity/Quality:

99.9% ^*data from raw suppliers

N-DeethoxymethylChlorfenapyr ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2=C(C(=C(N2)C(F)(F)F)Br)C#N)Cl
• 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.
• 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.

Technology Process of Tralopyril

There total 5 articles about Tralopyril which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

2-(p-chlorophenyl)-5-(trifluoromethyl)-pyrrole-3-carbonitrile (122454-23-3) → tralopyril (122454-29-9)

Guidance literature:

With bromine; sodium acetate; In acetic acid; for 2h; Heating;

DOI:10.1002/ps.2780410312

Reference yield: 22.9%

→ tralopyril (122454-29-9)

Guidance literature:

Reference yield:

4-Cyanochlorobenzene (623-03-0) → tralopyril (122454-29-9)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium tert-butylate / 7 h / 70 °C

2: toluene-4-sulfonic acid / cyclohexane / 4 h / 55 °C

3: bromine / cyclohexane / 0.75 h / 50 °C

With potassium tert-butylate; bromine; toluene-4-sulfonic acid; In cyclohexane;

upstream raw materials:

2-(p-chlorophenyl)-5-(trifluoromethyl)-pyrrole-3-carbonitrile

2-(4-Chlorophenyl)glycine

4-(p-chlorophenyl)-2-(trifluoromethyl)-1,3-oxazol-5-one

4-Cyanochlorobenzene

Downstream raw materials:

chlorfenapyr

N-((3-bromo-5-(4-chlorophenyl)-4-cyano-2-(trifluoromethyl)-1H-pyrrol-1-yl) methyl) acetamide

4-bromo-1-((2-chloroethoxy)methyl)-2-(4-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile

Refernces

• 1、 Dai, Jianrong,Feng, Bainian,Qu, Guoli,Xing, Yuntian,Yao, Jiakai. "Evaluation of the molluscicidal activities of arylpyrrole on Oncomelania hupensis, the intermediate host of Schistosoma japonicum". . . Retrieved 2021/10/01.
• 2、 -. "Application of 2-aryl substituted pyrrole compound in medicine for killing biomphalarid snails". Paragraph 0156; 0165; 0166. . Retrieved 2019/01/08.