72652-32-5

Basic information

• Product Name: 1-(4-BROMO-1H-PYRROL-2-YL)-2,2,2-TRICHLORO-1-ETHANONE
• Synonyms: 1-(4-BROMO-1H-PYRROL-2-YL)-2,2,2-TRICHLORO-1-ETHANONE;1-(4-BROMO-1H-PYRROL-2-YL)-2,2,2-TRICHLOROETHAN-1-ONE;1-(4-BROMO-1H-PYRROL-2-YL)-2,2,2-TRICHLOROETHANONE;4-Bromo-2-(trichloroacetyl)-1H-pyrrole;1-(4-Bromo-1H-pyrrol-2-yl)-2,2,2-trichloroethan-1-one, 4-Bromo-2-(2,2,2-trichloroethanoyl)-1H-pyrrole;Ethanone, 1-(4-bromo-1H-pyrrol-2-yl)-2,2,2-trichloro-
• CAS NO: 72652-32-5
• Molecular Formula: C₆H₃BrCl₃NO
• Molecular Weight: 291.36
• Mol File: 72652-32-5.mol
• Article Data: 25

Chemical Properties

• Melting Point: 134 °C
• Boiling Point: 351.5°C at 760 mmHg
• Flash Point: 166.4°C
• Appearance: /
• Density: 1.946g/cm³
• Vapor Pressure: 4.09E-05mmHg at 25°C
• Refractive Index: 1.625
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 1-(4-BROMO-1H-PYRROL-2-YL)-2,2,2-TRICHLORO-1-ETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-BROMO-1H-PYRROL-2-YL)-2,2,2-TRICHLORO-1-ETHANONE(72652-32-5)
• EPA Substance Registry System: 1-(4-BROMO-1H-PYRROL-2-YL)-2,2,2-TRICHLORO-1-ETHANONE(72652-32-5)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 72652-32-5(Hazardous Substances Data)

Usage

General Description

1-(4-Bromo-1H-pyrrol-2-yl)-2,2,2-trichloro-1-ethanone is a chemical compound with the molecular formula C4H2BrCl3NO. It is a trichloroethanone derivative with a 4-bromo-1H-pyrrol-2-yl substituent. 1-(4-BROMO-1H-PYRROL-2-YL)-2,2,2-TRICHLORO-1-ETHANONE is used in the field of pharmaceuticals and research as a building block for the synthesis of other organic compounds. It is important to handle this chemical with proper care and following safety protocols due to its potential hazards and toxicity. Its properties and structure make it a valuable component in the development of various medicinal and chemical compounds.

InChI:InChI=1/C6H3BrCl3NO/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

• 27746-02-7 4-bromo-1H-pyrrole-2-carboxylic acid 
• 1062368-32-4 methyl 3-(4-methoxyphenyl)-8-quinolin-4-yl-pyrrolo[1,2-a]pyrimidine-6-carboxylate 
• 98026-79-0 3-bromo-1H-pyrrole-2,5-dione 
• 1221420-51-4 3-[4-(2-cyclopropyl-2-hydroxy-ethoxy)-3-methoxy-phenyl]-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one 
• 1221420-50-3 6-bromo-3-[4-(2-cyclopropyl-2-hydroxy-ethoxy)-3-methoxy-phenyl]-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one 
• 1221419-99-3 6-(5-chloropyrimidin-2-yl)-3-(4-((3,3-difluoro-1-hydroxycyclobutyl)methoxy)-3-methoxyphenyl)pyrrolo[1,2-f][1,2,4]triazin-4(3H)-one 
• 1221420-02-5 (S)-6-(5-chloropyrimidin-2-yl)-3-(4-(3-(ethylsulfonyl)-2-hydroxypropoxy)-3-methoxyphenyl)pyrrolo[1,2-f][1,2,4]triazin-4(3H)-one 
• 1221420-05-8 (S)-6-(5-chloropyridin-2-yl)-3-(4-(3-(ethylsulfonyl)-2-hydroxypropoxy)-3-methoxyphenyl)pyrrolo[1,2-f][1,2,4]triazin-4(3H)-one 
• 1221419-86-8 (R)-6-(5-chloropyridin-2-yl)-3-(4-(2-cyclopropyl-2-hydroxy-ethoxy)-3-methoxy-phenyl)pyrrolo[1,2-f][1,2,4]triazin-4(3H)-one 
• 1221419-83-5 6-(4-chlorophenyl)-3-(4-((3,3-difluoro-1-hydroxycyclobutyl)methoxy)-3-methoxyphenyl)pyrrolo[1,2-f][1,2,4]triazin-4(3H)-one 

Relevant articles and documents

One-Pot Friedel-Crafts/Robinson-Gabriel Synthesis of the Indole-Oxazole Scaffold and Its Application to the Synthesis of Breitfussins C, G, and H

The indole-oxazole scaffold is found in a range of biologically active natural products, including the breitfussin family. Divergent methods that provide access to the indole-oxazole template are relatively scarce, which impedes the wider exploration of these natural products and their exciting biological activity. Herein, we describe a highly divergent synthesis of the indole-oxazole scaffold via a one-pot Friedel-Crafts/Robinson-Gabriel synthesis and the application of this methodology to the synthesis of breitfussins C, G, and H.

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.

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.