58905-16-1

Basic information

• Product Name: 1-(2,4-DICHLOROLPHENYL)-2-(1H-1,2,4-TRIAZOLE-1-YL)-ETHANONE
• Synonyms: 1-(2,4-DICHLOROLPHENYL)-2-(1H-1,2,4-TRIAZOLE-1-YL)-ETHANONE;2',4'-DICHLORO-2-(1,2,4 TRIAZOL-1YL) ACETOPHENONE;Ethanone, 1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-;1-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone
• CAS NO: 58905-16-1
• Molecular Formula: C₁₀H₇Cl₂N₃O
• Molecular Weight: 256.09
• Mol File: 58905-16-1.mol
• Article Data: 51

Chemical Properties

• Melting Point: 160-161 °C
• Boiling Point: 428.5°C at 760 mmHg
• Flash Point: 213°C
• Appearance: /
• Density: 1.48g/cm³
• Vapor Pressure: 1.5E-07mmHg at 25°C
• Refractive Index: 1.658
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), DMSO (Slightly)
• PKA: 2.03±0.10(Predicted)
• CAS DataBase Reference: 1-(2,4-DICHLOROLPHENYL)-2-(1H-1,2,4-TRIAZOLE-1-YL)-ETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,4-DICHLOROLPHENYL)-2-(1H-1,2,4-TRIAZOLE-1-YL)-ETHANONE(58905-16-1)
• EPA Substance Registry System: 1-(2,4-DICHLOROLPHENYL)-2-(1H-1,2,4-TRIAZOLE-1-YL)-ETHANONE(58905-16-1)

Safety Data

• Hazardous Substances Data: 58905-16-1(Hazardous Substances Data)

Usage

Description

1-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazole-1-yl)ethanone is an organic compound that serves as a crucial intermediate in the synthesis of various chemical compounds, particularly those related to Propiconazole (P770100).

Uses

Used in Pharmaceutical Industry:
1-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazole-1-yl)ethanone is used as a synthetic intermediate for the production of Propiconazole (P770100) and its related compounds. Propiconazole is a widely used antifungal agent, effective against a broad range of fungal infections. It is commonly utilized in the treatment of plant diseases caused by fungi, as well as in the medical field for treating human fungal infections.
Used in Chemical Synthesis:
1-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazole-1-yl)ethanone is also used as a key building block in the synthesis of other chemical compounds, particularly those with potential applications in various industries such as agriculture, pharmaceuticals, and materials science. Its unique chemical structure allows for further functionalization and modification, enabling the development of new molecules with diverse properties and applications.

InChI:InChI=1/C10H7Cl2N3O/c11-7-1-2-8(9(12)3-7)10(16)4-15-6-13-5-14-15/h1-3,5-6H,4H2

Upstream product

• 56-84-8 L-Aspartic acid 
• 2986-19-8 carbamimidothioic acid methyl ester 
• 2440-60-0 2-methyl-isourea 
• 867-44-7 S-Methylisothiourea sulfate 
• 288-88-0 1,2,4-Triazole 
• 4252-78-2 2,2',4'-trichloroacetophenone 
• 118227-30-8 1-(2,4-dichlorophenyl)-2-(4-amino-4H-1,2,4-triazoliumyl)ethanone chloride 
• 126961-67-9 4-Amino-1-[2-(2,4-dichloro-phenyl)-2-oxo-ethyl]-4H-[1,2,4]triazol-1-ium; bromide 
• 130235-53-9 erythro-1-(2,4-dichlorophenyl)-1-(3-oxothiolan-2-yl)-2-(1H-1,2,4-triazol-1-yl)ethanol 
• 2631-72-3 2,4-dichlorophenacyl bromide 
• 584-13-4 4-amino-1,2,4-triazole 
• 60207-90-1 Propiconazole 
• 2234-16-4 1-(2,4-dichlorophenyl)ethan-1-one 
• 130235-45-9 3-[2-(2,4-Dichloro-phenyl)-2-oxo-ethylsulfanyl]-propionic acid 

Downstream Products

• 81886-52-4 2-(2,4-dichlorophenyl)-1,3-di(1H-1,2,4-triazolyl)-2-propanol 
• 139540-08-2 Propionic acid (Z)-1-(2,4-dichloro-phenyl)-2-[1,2,4]triazol-1-yl-vinyl ester 
• 139540-16-2 1-{2-[2-(2,4-Dichloro-phenyl)-2-oxo-ethyl]-2H-[1,2,4]triazol-3-yl}-propan-1-one 
• 139540-09-3 2,2-Dimethyl-propionic acid (Z)-1-(2,4-dichloro-phenyl)-2-[1,2,4]triazol-1-yl-vinyl ester 
• 129994-08-7 2,4-dichlorophenyl(1H-1,2,4-triazol-1-ylmethyl)ketone enol acetate 
• 129994-09-8 2,4-dichlorophenyl(5-acetyl-1H-1,2,4-triazol-1-ylmethyl)ketone 
• 139540-10-6 Hexanoic acid (Z)-1-(2,4-dichloro-phenyl)-2-[1,2,4]triazol-1-yl-vinyl ester 
• 89544-40-1 1-[2-(2,4-dichlorophenyl)-2-hydroxy-4-pentenyl](1H)1,2,4-triazole 
• 139540-06-0 C₁₂H₆⁽²⁾H₃Cl₂N₃O₂ 
• 123871-87-4 (E)-2-(2,4-Dichloro-phenyl)-1-[1,2,4]triazol-1-yl-5-trimethylsilanyl-pent-4-en-2-ol 
• 126086-54-2 3-(2,4-Dichloro-phenyl)-3-hydroxy-4-[1,2,4]triazol-1-yl-butyric acid octyl ester 
• 126112-95-6 3-(2,4-Dichloro-phenyl)-3-hydroxy-4-[1,2,4]triazol-1-yl-butyric acid dodecyl ester 
• 159382-00-0 4-[(Z)-3-(2,4-Dichloro-phenyl)-3-oxo-2-[1,2,4]triazol-1-yl-propenyl]-benzaldehyde 
• 159381-97-2 (Z)-1-(2,4-Dichloro-phenyl)-3-(4-[1,3]dioxolan-2-yl-phenyl)-2-[1,2,4]triazol-1-yl-propenone 

Relevant articles and documents

Phototransformation of propiconazole in aqueous media

The photolysis of propiconazole in pure water, in water containing humic substances, and in natural water was investigated. The reaction rates were determined, and the main photoproducts were identified with the help of HPLC-mass spectrometry and by NMR.

Lead optimization generates selenium-containing miconazole CYP51 inhibitors with improved pharmacological profile for the treatment of fungal infections

A series of selenium-containing miconazole derivatives were identified as potent antifungal drugs in our previous study. Representative compound A03 (MIC = 0.01 μg/mL against C.alb. 5314) proved efficacious in inhibiting the growth of fungal pathogens. However, further study showed lead compound A03 exhibited potential hemolysis, significant cytotoxic effect and unfavorable metabolic stability and was therefore modified to overcome these drawbacks. In this article, the further optimization of selenium-containing miconazole derivatives resulted in the discovery of similarly potent compound B17 (MIC = 0.02 μg/mL against C.alb. 5314), exhibiting a superior pharmacological profile with decreased rate of metabolism, cytotoxic effect and hemolysis. Furthermore, compound B17 showed fungicidal activity against Candida albicans and significant effects on the treatment of resistant Candida albicans infections. Meanwhile, compound B17 not only could reduce the ergosterol biosynthesis pathway by inhibiting CYP51, but also inhibited biofilm formation. More importantly, compound B17 also shows promising in vivo efficacy after intraperitoneal injection and the PK study of compound B17 was evaluated. In addition, molecular docking studies provide a model for the interaction between the compound B17 and the CYP51 protein. Overall, we believe that these selenium-containing miconazole compounds can be further developed for the potential treatment of fungal infections.

Design and Synthesis of Tetrazole- And Pyridine-Containing Itraconazole Analogs as Potent Angiogenesis Inhibitors

Itraconazole, a widely used antifungal drug, was found to possess antiangiogenic activity and is currently undergoing multiple clinical trials for the treatment of different types of cancer. However, it suffers from extremely low solubility and strong interactions with many drugs through inhibition of CYP3A4, limiting its potential as a new antiangiogenic and anticancer drug. To address these issues, a series of analogs in which the phenyl group is replaced with pyridine or fluorine-substituted benzene was synthesized. Among them the pyridine- and tetrazole-containing compound 24 has significantly improved solubility and reduced CYP3A4 inhibition compared to itraconazole. Similar to itraconazole, compound 24 inhibited the AMPK/mTOR signaling axis and the glycosylation of VEGFR2. It also induced cholesterol accumulation in the endolysosome and demonstrated binding to the sterol-sensing domain of NPC1 in a simulation study. These results suggested that compound 24 may serve as an attractive candidate for the development of a new generation of antiangiogenic drug.

insecticide compositions, insecticidal products containing them and methods of eradicating pests using them

Styryltriazole compounds having activity as antiparasitic hormone antagonists. Provided are an insecticide composition comprising an isomer or a pharmaceutically acceptable salt thereof, an insecticide product comprising the same, and a method for combating pests using the same.