22019-49-4

Basic information

• Product Name: 2-BROMO-1-(4-CHLORO-3-NITROPHENYL)ETHAN-1-ONE
• Synonyms: 2-BROMO-1-(4-CHLORO-3-NITROPHENYL)ETHAN-1-ONE;4-CHLORO-3-NITROPHENACYLBROMIDE;2-bromo-3-nitro-4-chloroacetophenone;2-Bromo-1-(4-chloro-3-nitrophenyl)ethan-1-one , Tech.
• CAS NO: 22019-49-4
• Molecular Formula: C₈H₅BrClNO₃
• Molecular Weight: 278.49
• Product Categories: Aromatic Halides (substituted)
• Mol File: 22019-49-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 86-89°C
• Boiling Point: 336.1°Cat760mmHg
• Flash Point: 157.1°C
• Appearance: /
• Density: 1.763g/cm³
• Vapor Pressure: 0.000115mmHg at 25°C
• Refractive Index: 1.619
• CAS DataBase Reference: 2-BROMO-1-(4-CHLORO-3-NITROPHENYL)ETHAN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMO-1-(4-CHLORO-3-NITROPHENYL)ETHAN-1-ONE(22019-49-4)
• EPA Substance Registry System: 2-BROMO-1-(4-CHLORO-3-NITROPHENYL)ETHAN-1-ONE(22019-49-4)

Safety Data

• Hazard Codes: C:Corrosive
• Statements: 36/37/38
• Safety Statements: 22-24/25
• Hazardous Substances Data: 22019-49-4(Hazardous Substances Data)

Usage

General Description

2-BROMO-1-(4-CHLORO-3-NITROPHENYL)ETHAN-1-ONE is a chemical compound with the molecular formula C8H6BrClNO3. It is a derivative of 4-chloro-3-nitroacetophenone, and is commonly used as a building block in organic synthesis. The compound is an alpha-bromo ketone, which makes it a versatile intermediate for the synthesis of various pharmaceuticals and agrochemicals. It is also known for its use in the preparation of synthetic cannabinoids. 2-BROMO-1-(4-CHLORO-3-NITROPHENYL)ETHAN-1-ONE is a highly reactive compound that requires careful handling and must be stored and used in a controlled environment to ensure safety.

InChI:InChI=1/C8H5BrClNO3/c9-4-8(12)5-1-2-6(10)7(3-5)11(13)14/h1-3H,4H2

Upstream product

• 5465-65-6 4-chloro-3-nitroacetophenone 

Downstream Products

• 135718-56-8 2-Chloro-6-(4-chloro-3-nitro-phenyl)-imidazo[2,1-b]thiazole 
• 143417-76-9 N'-{1-[(Z)-2-(4-Chloro-3-nitro-phenyl)-2-oxo-ethylimino]-ethyl}-hydrazinecarboxylic acid ethyl ester 
• 126751-09-5 2-Amino-4-(4-chloro-3-nitrophenyl)thiazole 
• 308121-68-8 6-(4-chloro-3-nitrophenyl)imidazo[2,1-b]thiazole 
• 871933-01-6 1-(4-chloro-3-nitrophenyl)-2-(N,N-diformylamino)-ethanone 
• 92659-56-8 4-(4-chloro-3-nitro-phenyl)-1⁽³⁾H-imidazole 
• 916051-60-0 4-(4-chloro-3-nitrophenyl)-1,3-oxazole 
• 871933-03-8 5-(4-chloro-3-nitrophenyl)-2-(4-chlorophenyl)-oxazole 
• 871933-02-7 4-chloro-N-[2-(4-chloro-3-nitrophenyl)-2-oxo-ethyl]-benzamide 
• 61424-42-8 (+/-)-2-bromo-1-(4-chloro-3-nitrophenyl)ethanol 
• 135718-52-4 6-(4-Chloro-3-nitro-phenyl)-2,3-dimethyl-imidazo[2,1-b]thiazole 
• 916051-51-9 (5Z)-2-{[2-chloro-5-(2-methyl-1,3-thiazol-4-yl)phenyl]amino}-5-(6-quinolinylmethylidene)-1,3-thiazol-4(5H)-one 
• 916051-48-4 (5Z)-2-{[2-chloro-5-(1H-imidazol-4-yl)phenyl]amino}-5-(6-quinolinylmethylidene)-1,3-thiazol-4(5H)-one 

Relevant articles and documents

Nucleus-independent chemical shift (NICS) as a criterion for the design of new antifungal benzofuranones

The assertion made by Wu et al. that aromaticity may have considerable implications for molecular design motivated us to use nucleus-independent chemical shifts (NICS) as an aromaticity criterion to evaluate the antifungal activity of two series of indol-4-ones. A linear regression analysis of NICS and antifungal activity showed that both tested variables were significantly related (p –1 for Candida glabrata, Candida krusei and Candida guilliermondii with compounds 15-32, 15-15 and 15-1. The MIC for filamentous fungi was 1.95 μg·mL–1 for Aspergillus niger for compounds 15-1, 15-33 and 15-34. The results obtained support the use of NICS in the molecular design of compounds with antifungal activity.

Highlights of the Structure-Activity Relationships of Benzimidazole Linked Pyrrolidines Leading to the Discovery of the Hepatitis C Virus NS5A Inhibitor Pibrentasvir (ABT-530)

Curative interferon and ribavirin sparing treatments for hepatitis C virus (HCV)-infected patients require a combination of mechanistically orthogonal direct acting antivirals. A shared component of these treatments is usually an HCV NS5A inhibitor. First generation FDA approved treatments, including the component NS5A inhibitors, do not exhibit equivalent efficacy against HCV virus genotypes 1-6. In particular, these first generation NS5A inhibitors tend to select for viral drug resistance. Ombitasvir is a first generation HCV NS5A inhibitor included as a key component of Viekira Pak for the treatment of patients with HCV genotype 1 infection. Since the launch of next generation HCV treatments, functional cure for genotype 1-6 HCV infections has been achieved, as well as shortened treatment duration across a wider spectrum of genotypes. In this paper, we show how we have modified the anchor, linker, and end-cap architecture of our NS5A inhibitor design template to discover a next generation NS5A inhibitor pibrentasvir (ABT-530), which exhibits potent inhibition of the replication of wild-type genotype 1-6 HCV replicons, as well as improved activity against replicon variants demonstrating resistance against first generation NS5A inhibitors.

Anti-Viral Compounds

Compounds effective in inhibiting replication of Hepatitis C virus (“HCV”) are described. This invention also relates to processes of making such compounds, compositions comprising such compounds, and methods of using such compounds to treat HCV infection.