79779-66-1

Basic information

• Product Name: 2-bromo-1-(2,3,4-trichlorophenyl)ethan-1-one
• Synonyms: 2-bromo-1-(2,3,4-trichlorophenyl)ethan-1-one;α-Bromo-2',3',4'-trichloroacetophenone;2-Bromo-1-(2,3,4-trichlorophenyl)ethanone
• CAS NO: 79779-66-1
• Molecular Formula: C₈H₄BrCl₃O
• Molecular Weight: 302.37976
• EINECS: 279-258-3
• Mol File: 79779-66-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 41-43 °C
• Boiling Point: 344.6°C at 760 mmHg
• Flash Point: 162.2°C
• Appearance: /
• Density: 1.778g/cm³
• Vapor Pressure: 6.53E-05mmHg at 25°C
• Refractive Index: 1.606
• CAS DataBase Reference: 2-bromo-1-(2,3,4-trichlorophenyl)ethan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-bromo-1-(2,3,4-trichlorophenyl)ethan-1-one(79779-66-1)
• EPA Substance Registry System: 2-bromo-1-(2,3,4-trichlorophenyl)ethan-1-one(79779-66-1)

Safety Data

• Hazardous Substances Data: 79779-66-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H4BrCl3O/c9-3-6(13)4-1-2-5(10)8(12)7(4)11/h1-2H,3H2

Upstream product

• 13608-87-2 2',3',4'-trichloroacetophenone 

Downstream Products

• 91064-45-8 2-(2-imino-thiazolidin-3-yl)-1-(2,3,4-trichloro-phenyl)-ethanone 
• 156897-25-5 2,2-Dimethyl-7-phenyl-6-(2,3,4-trichloro-phenyl)-2,3-dihydro-1H-pyrrolizine 
• 178449-59-7 6-(2,3,4-Trichloro-phenyl)-2,3-dihydro-imidazo[2,1-b]thiazole 
• 178449-58-6 6-(2,3,4-Trichloro-phenyl)-imidazo[2,1-b]thiazole 
• 936105-14-5 5-[1,2,4]triazol-1-yl-4-(2,3,4-trichloro-phenyl)-thiazol-2-ylamine 
• 178449-62-2 6-(2,3,4-Trichloro-phenyl)-2,3-dihydro-imidazo[2,1-b]thiazole-5-carbaldehyde 
• 178449-61-1 6-(2,3,4-Trichloro-phenyl)-imidazo[2,1-b]thiazole-5-carbaldehyde 
• 156897-39-1 [6,6-Dimethyl-1-phenyl-2-(2,3,4-trichloro-phenyl)-6,7-dihydro-5H-pyrrolizin-3-yl]-acetic acid ethyl ester 
• 6649-41-8 2-(2-acetylimino-thiazolidin-3-yl)-1-(2,3,4-trichloro-phenyl)-ethanone 
• 5028-86-4 2-(2-acetylimino-thiazolidin-3-yl)-1-(2,3,4-trichloro-phenyl)-ethanol 

Relevant articles and documents

Structural design, synthesis and structure-activity relationships of thiazolidinones with enhanced anti-Trypanosoma cruzi activity

Pharmacological treatment of Chagas disease is based on benznidazole, which displays poor efficacy when administered during the chronic phase of infection. Therefore, the development of new therapeutic options is needed. This study reports on the structural design and synthesis of a new class of anti-Trypanosoma cruzi thiazolidinones (4 a-p). (2-[2-Phenoxy-1-(4-bromophenyl) ethylidene)hydrazono]-5-ethylthiazolidin-4-one (4 h) and (2-[2-phenoxy-1-(4- phenylphenyl)ethylidene)hydrazono]-5-ethylthiazolidin-4-one (4 l) were the most potent compounds, resulting in reduced epimastigote proliferation and were toxic for trypomastigotes at concentrations below 10 μM, while they did not display host cell toxicity up to 200 μM. Thiazolidinone 4 h was able to reduce the in vitro parasite burden and the blood parasitemia in mice with similar potency to benznidazole. More importantly, T. cruzi infection reduction was achieved without exhibiting mouse toxicity. Regarding the molecular mechanism of action, these thiazolidinones did not inhibit cruzain activity, which is the major trypanosomal protease. However, investigating the cellular mechanism of action, thiazolidinones altered Golgi complex and endoplasmic reticulum (ER) morphology, produced atypical cytosolic vacuoles, as well as induced necrotic parasite death. This structural design employed for the new anti-T. cruzi thiazolidinones (4 a-p) led to the identification of compounds with enhanced potency and selectivity compared to first-generation thiazolidinones. These compounds did not inhibit cruzain activity, but exhibited strong antiparasitic activity by acting as parasiticidal agents and inducing a necrotic parasite cell death. Stop the cycle! The attachment of an aryl ring to the iminic carbon produced thiazolidinones that are conformationally more restricted than first-generation thiazolidinones. This enhanced the potency of antiparasitic thiazolidinones, as observed under treatment with compound 4 h where parasite development and invasion in host cells were substantially reduced. Copyright

Synthesis, structure, and biological activity of novel 1H-1,2,4-triazol-1- yl-thiazole derivatives

2-Amino-4-aryl-5-(1H-1,2,4-triazol-1-yl)thiazole derivatives were synthesized from the reaction of α-bromo substituted acetophenone and thiourea. The structures were confirmed by elemental analysis, 1H NMR and single crystal X-ray diffraction analysis. Biological evaluation showed that some of them possess antifungal and plant growth regulatory activities. Copyright Taylor & Francis Group, LLC.