50371-52-3

Basic information

• Product Name: 2,2,2-TRICHLORO-1-(4,5-DIBROMO-1H-PYRROL-2-YL)-1-ETHANONE
• Synonyms: 2,2,2-TRICHLORO-1-(4,5-DIBROMO-1H-PYRROL-2-YL)-1-ETHANONE;2,3-Dibromo-5-(trichloroacetyl)-1H-pyrrole;2,2,2-Trichloro-1-(4,5-dibromo-1H-pyrrol-2-yl)ethanone
• CAS NO: 50371-52-3
• Molecular Formula: C₆H₂Br₂Cl₃NO
• Molecular Weight: 370.25
• Mol File: 50371-52-3.mol
• Article Data: 23

Chemical Properties

• Melting Point: 137-139°C
• Boiling Point: 415.9°C at 760 mmHg
• Flash Point: 205.3°C
• Appearance: /
• Density: 2.232g/cm³
• Vapor Pressure: 3.99E-07mmHg at 25°C
• Refractive Index: 1.651
• CAS DataBase Reference: 2,2,2-TRICHLORO-1-(4,5-DIBROMO-1H-PYRROL-2-YL)-1-ETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,2-TRICHLORO-1-(4,5-DIBROMO-1H-PYRROL-2-YL)-1-ETHANONE(50371-52-3)
• EPA Substance Registry System: 2,2,2-TRICHLORO-1-(4,5-DIBROMO-1H-PYRROL-2-YL)-1-ETHANONE(50371-52-3)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 50371-52-3(Hazardous Substances Data)

Usage

General Description

2,2,2-Trichloro-1-(4,5-dibromo-1H-pyrrol-2-yl)-1-ethanone, also known as triclosan, is a synthetic chemical commonly used as an antibacterial and antifungal agent in personal care products, such as soaps, toothpaste, and body wash. It is also used in textiles, plastics, and kitchenware. Triclosan has been found to persist in the environment, accumulating in water and soil, and has been detected in human tissues and breast milk. Concerns have been raised about its potential harmful effects on human health and the environment, leading to restrictions and bans on its use in certain products in some countries.

InChI:InChI=1/C6H2Br2Cl3NO/c7-2-1-3(12-5(2)8)4(13)6(9,10)11/h1,12H

Upstream product

• 35302-72-8 pyrrol-2-yl trichloromethyl ketone 

Downstream Products

• 574002-72-5 4,5-dibromo-1H-pyrrole-2-carboxylic acid [3-(2-amino-1-trityl-1H-imidazol-4-yl)-prop-2-ynyl]-amide 
• 848899-39-8 4,5-dibromo-1H-pyrrole-2-carboxylic acid [3-(2-phenylsulfanyl-3H-imidazol-4-yl)propyl]amide 
• 1454645-90-9 N-benzyl-4,5-dibromo-1H-pyrrole-2-carboxamide 
• 1408287-97-7 C₄₇H₄₅Br₂N₈O₅P 
• 1408287-94-4 C₄₇H₄₃Br₄N₈O₅P 
• 1408288-04-9 C₄₈H₄₃Br₄N₁₀O₃P*C₂HF₃O₂ 
• 1408287-99-9 C₅₃H₅₁Br₂N₁₀O₆P 
• 1408287-98-8 C₅₈H₆₃Br₂N₁₀O₉P 
• 1408287-96-6 C₅₃H₄₉Br₄N₁₀O₆P 
• 1408287-95-5 C₅₈H₆₁Br₄N₁₀O₉P 

Relevant articles and documents

A convenient synthesis of pseudoceratidine and three analogs for biological evaluation

The recently isolated marine natural product pseudoceratidine (1) has been synthesized from 2-trichloronactylpyrrole. Bromination in the 4- and 5-position followed by nucleophilic displacement of the trichloromethyl group with spermidine gave 1 in 79% yield. The procedure is general and can easily be adopted to the preparation of other derivatives. This was demonstrated by the synthesis of a 5,5'-didebromo derivative (2) and two analogs (3-4). The compounds 1-4 have been tested for antibacterial activity and the results compared to a previous study. Also activity against die marine brine shrimp Artemia salina is reported.

From Synthetic Simplified Marine Metabolite Analogues to New Selective Allosteric Inhibitor of Aurora B Kinase

Significant inhibition of Aurora B was achieved by the synthesis of simplified fragments of benzosceptrins and oroidin belonging to the marine pyrrole-2-aminoimidazoles metabolites isolated from sponges. Evaluation of kinase inhibition enabled the discovery of a synthetically accessible rigid acetylenic structural analogue EL-228 (1), whose structure could be optimized into the potent CJ2-150 (37). Here we present the synthesis of new inhibitors of Aurora B kinase, which is an important target for cancer therapy through mitosis regulation. The biologically oriented synthesis yielded several nanomolar inhibitors. The optimized compound CJ2-150 (37) showed a non-ATP competitive allosteric mode of action in a mixed-type inhibition for Aurora B kinase. Molecular docking identified a probable binding mode in the allosteric site "F"and highlighted the key interactions with the protein. We describe the improvement of the inhibitory potency and specificity of the novel scaffold as well as the characterization of the mechanism of action.

Synthesis of 4,4-dimethyl-2-(2-pyrrolyl)-2-oxazolines

– A practical synthesis of 4,4-dimethyl-2-oxazolines on pyrrole was achieved via the cyclization of the corresponding amides, which were derived from the trichloroacetylpyrroles. The established conditions were applicable to pyrroles bearing a ketone or an ester moiety. In addition to pyrroles, the method could be extended to the synthesis of the indole derivative.

Synthesis and Absolute Stereochemical Reassignment of Mukanadin F: A Study of Isomerization of Bromopyrrole Alkaloids with Implications on Marine Natural Product Isolation

Synthesis of both enantiomers of mukanadin F was achieved by using a seven step synthesis. Comparison of the optical rotation data of synthetic samples to that reported for the isolated natural product determined that the absolute configuration of the natural product is 9S and not the reported 9R. Further studies established that the reported low magnitude of optical rotation in the isolated sample is due to compounds of this type undergoing isomerization and racemization under benign laboratory conditions. Additionally the synthetic methods developed were applied to synthesize mukanadins B and D.