72652-31-4

Basic information

• Product Name: 2,2,2-TRICHLORO-1-(4-CHLORO-1H-PYRROL-2-YL)ETHANONE
• Synonyms: 2,2,2-Trichloro-1-(4-chloro-1H-pyrrol-2-yl)ethanone
• CAS NO: 72652-31-4
• Molecular Formula: C₆H₃Cl₄NO
• Molecular Weight: 246.91
• Mol File: 72652-31-4.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 334.1°C at 760 mmHg
• Flash Point: 155.8°C
• Appearance: /
• Density: 1.697g/cm³
• Vapor Pressure: 0.000131mmHg at 25°C
• Refractive Index: 1.605
• CAS DataBase Reference: 2,2,2-TRICHLORO-1-(4-CHLORO-1H-PYRROL-2-YL)ETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,2-TRICHLORO-1-(4-CHLORO-1H-PYRROL-2-YL)ETHANONE(72652-31-4)
• EPA Substance Registry System: 2,2,2-TRICHLORO-1-(4-CHLORO-1H-PYRROL-2-YL)ETHANONE(72652-31-4)

Safety Data

• Hazardous Substances Data: 72652-31-4(Hazardous Substances Data)

Usage

General Description

2,2,2-TRICHLORO-1-(4-CHLORO-1H-PYRROL-2-YL)ETHANONE is a chemical compound that contains three chlorine atoms and a pyrrole ring. It is commonly used in the synthesis of various organic compounds, and it is known for its strong and distinct odor. This chemical has potential applications in the pharmaceutical and agrochemical industries due to its unique structure and properties. It is important to handle this compound with care and follow proper safety procedures when working with it in a laboratory setting.

InChI:InChI=1/C6H3Cl4NO/c7-3-1-4(11-2-3)5(12)6(8,9)10/h1-2,11H

Upstream product

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

Downstream Products

• 1194-96-3 4-chloro-1H-pyrrole-2-carboxylic acid methyl ester 
• 27746-03-8 4-chloro-1H-pyrrole-2-carboxylic acid 
• 915229-96-8 4-chloro-1H-pyrrole-2-carboxylic acid amide 
• 57097-45-7 4-Chloropyrrol-2-carbonitril 
• 1197-12-2 4,5-Dichlor-1H-pyrrol-2-carbonsaeure-methylester 

Relevant articles and documents

Synthesis and antibacterial analysis of analogues of the marine alkaloid pseudoceratidine

In an effort to gain more understanding on the structure activity relationship of pseudoceratidine 1, a di-bromo pyrrole spermidine alkaloid derived from the marine sponge Pseudoceratina purpurea that has been shown to exhibit potent biofouling, anti-fungal, antibacterial, and anti-malarial activities, a large series of 65 compounds that incorporated several aspects of structural variation has been synthesised through an efficient, divergent method that allowed for a number of analogues to be generated from common precursors. Subsequently, all analogues were assessed for their antibacterial activity against both Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli) bacteria. Overall, several compounds exhibited comparable or better activity than that of pseudoceratidine 1, and it was found that this class of compounds is generally more effective against Gram-positive than Gram-negative bacteria. Furthermore, altering several structural features allowed for the establishment of a comprehensive structure activity relationship (SAR), where it was concluded that several structural features are critical for potent anti-bacterial activity, including di-halogenation (preferable bromine, but chlorine is also effective) on the pyrrole ring, two pyrrolic units in the structure and with one or more secondary amines in the chain adjoining these units, with longer chains giving rise to better activities.

Story of an Age-Old Reagent: An Electrophilic Chlorination of Arenes and Heterocycles by 1-Chloro-1,2-benziodoxol-3-one

By the use of 1-chloro-1,2-benziodoxol-3-one, an age-old reagent, the practical and efficient chlorination method is achieved. This hypervalent iodine reagent is amenable not only to the chlorination of nitrogen-containing heterocycles but also to selected classes of arenes, BODIPY dyes, and pharmaceuticals. In addition, the advantages, such as easy preparation and recyclable, air- and moisture-stable, in combination with the success in a gram-scale experiment grant this reagent great potential for industrial application.

Selective Halogenation Using an Aniline Catalyst

Electrophilic halogenation is used to produce a wide variety of halogenated compounds. Previously reported methods have been developed mainly using a reagent-based approach. Unfortunately, a suitable "catalytic" process for halogen transfer reactions has yet to be achieved. In this study, arylamines have been found to generate an N-halo arylamine intermediate, which acts as a highly reactive but selective catalytic electrophilic halogen source. A wide variety of heteroaromatic and aromatic compounds are halogenated using commercially available N-halosuccinimides, for example, NCS, NBS, and NIS, with good to excellent yields and with very high selectivity. In the case of unactivated double bonds, allylic chlorides are obtained under chlorination conditions, whereas bromocyclization occurs for polyolefin. The reactivity of the catalyst can be tuned by varying the electronic properties of the arene moiety of catalyst.