40945-79-7

Basic information

• Product Name: Ethyl 5-acetyloxy-1,2-dimethylindole-3-carboxylate
• Synonyms: ETHYL5-ACETOXY-1,2-DIMETHYLINDOLE-3-CARBOXYLATE;ETHYL 5-ACETYLOXY-1,2-DIMETHYLINDOLE-3-CARBOXYLATE;5-Acetoxy-1,2-dimethyl-1H-indole-3-carboxylic acid ethyl ester;ethyl 5-acetoxy-1,2-diMethyl-1H-indole-3-carboxylate
• CAS NO: 40945-79-7
• Molecular Formula: C₁₅H₁₇NO₄
• Molecular Weight: 275.3
• Product Categories: arbidol
• Mol File: 40945-79-7.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 414.1 °C at 760 mmHg
• Flash Point: 204.2 °C
• Appearance: /
• Density: 1.18 g/cm³
• Vapor Pressure: 4.57E-07mmHg at 25°C
• Refractive Index: 1.553
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Ethyl 5-acetyloxy-1,2-dimethylindole-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 5-acetyloxy-1,2-dimethylindole-3-carboxylate(40945-79-7)
• EPA Substance Registry System: Ethyl 5-acetyloxy-1,2-dimethylindole-3-carboxylate(40945-79-7)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 40945-79-7(Hazardous Substances Data)

Usage

General Description

Ethyl 5-acetyloxy-1,2-dimethylindole-3-carboxylate is a chemical compound with the molecular formula C16H17NO4. It is a derivative of the indole family, which is known for its diverse biological activities. This specific compound is commonly used as an intermediate in the synthesis of pharmaceuticals and organic compounds. Its structure consists of an indole ring with acetyloxy and carboxylate functional groups, making it useful in various chemical reactions and transformations. Additionally, it has potential applications in medicinal chemistry, especially in the development of new drugs and bioactive molecules due to its unique structural features.

InChI:InChI=1/C15H17NO4/c1-5-19-15(18)14-9(2)16(4)13-7-6-11(8-12(13)14)20-10(3)17/h6-8H,5H2,1-4H3

Upstream product

• 65578-36-1 ethyl N-methyl β-aminocrotonate 
• 108-24-7 acetic anhydride 
• 870-85-9 ethyl 3-methylaminocrotonate 
• 106-51-4 p-benzoquinone 
• 141-97-9 ethyl acetoacetate 
• 13871-68-6 p-aminophenyl acetate 
• 830-03-5 4-nitrophenol acetate 
• 100-02-7 4-nitro-phenol 
• 20862-91-3 ethyl 5-acetyloxy-2-methyl-1H-indole-3-carboxylate 
• 77-78-1 dimethyl sulfate 
• 15574-49-9 mecarbinate 
• 7598-91-6 ethyl 5-hydroxy-2-methylindole-3-carboxylate 
• 74-88-4 methyl iodide 
• 75-36-5 acetyl chloride 

Downstream Products

• 1615239-28-5 ethyl 5-hydroxy-2-((2-methoxyphenylthio)methyl)-1-methyl-1H-indole-3-carboxylate 
• 1615239-29-6 ethyl 5-hydroxy-2-((4-methoxyphenylthio)methyl)-1-methyl-1H-indole-3-carboxylate 
• 1615239-30-9 ethyl 5-hydroxy-1-methyl-2-((4-(trifluoromethoxy)phenylthio)methyl)-1H-indole-3-carboxylate 
• 1615239-31-0 ethyl 5-hydroxy-1-methyl-2-((2-(trifluoromethyl)phenylthio)methyl)-1H-indole-3-carboxylate 
• 1615239-32-1 ethyl 5-hydroxy-1-methyl-2-((4-(trifluoromethyl)phenylthio)methyl)-1H-indole-3-carboxylate 
• 1615239-33-2 ethyl 2-((4-fluorophenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate 
• 1615239-34-3 ethyl 2-((3-chlorophenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate 
• 1615239-36-5 ethyl 2-((2,6-dichlorophenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate 
• 1615239-37-6 ethyl 2-((2,6-dimethylphenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate 
• 1615239-38-7 ethyl 2-((3,5-dimethylphenylthio)methyl)-5-hydroxy-1-methyl-1H-indole-3-carboxylate 
• 1615239-39-8 ethyl 5-hydroxy-2-(mesitylthiomethyl)-1-methyl-1H-indole-3-carboxylate 
• 26065-16-7 ethyl 5-hydroxy-1-methyl-2-(phenylthiomethyl)-1H-indole-3-carboxylate 
• 131707-23-8 Arbidol hydrochloride 

Relevant articles and documents

An Urgent Industrial Scheme Both for Total Synthesis, and for Pharmaceutical Analytical Analysis of Umifenovir as an Anti-viral API for Treatment of COVID-19

Background: This paper aims to reveal an urgent industrial scheme for a fast and facile total synthesis of umifenovir (arbidol) (by one-pot stages) as an antiviral agent for treating the 2019-nCoV virus via inhibiting its viral replication in the human cells. As COVID-19 takes thousands of lives all around the world, it seems that the medicinal resources would not be enough to supply billions of peoples currently living on the planet. Thus, this pandemic and its subsequent impacts on the natural order of our life would be one of the most important threats against the entire human race. Methods: In this project, we have made attempts to find an operative approach for synthesizing this compound as an active pharmaceutical ingredient (API), which showed it could be effective in inhibiting the newly emerged coronavirus. Results: The designed scheme uses relatively cheap precursors and contains one pot stage instead of seven time-consuming and more costly linear steps. Moreover, safe and cheap solvents have been used like water and ethanol, instead of toxic ones like methanol and pyridine which could cause rejection of the API in the organic volatile impurities (OVI) test of pharmacopeia analysis, as well as increase the concern of inflammability, explosivity, and carcinogenic properties of those common solvents. Conclusion: The most important pharmaceutical analytical methods containing OVI test (mainly ethanol (about 171 ppm) much lower than the limits, by gas chromatography-Flame Ionization Detector (GC-FID) instrument), assay content (about 99.6% by potentiometric titration), and related purity analysis (by high-performance liquid chromatography-Ultraviolet Detector (HPLC-UV)) (about 99.8%) were performed and described to give a more clear industrial scheme.

Method for synthesizing arbidol hydrochloride intermediate

The invention discloses a method for synthesizing an arbidol hydrochloride intermediate, and belongs to the technical field of medical intermediates. According to the method, 5-hydroxy-1, 2-dimethylindole-3-carboxylic acid ethyl ester is used as a raw material, and esterification, bromination, thiophenol and deprotection, Mannich reaction and salification are performed to obtain arbidol hydrochloride. In the process of generating the most important intermediate 5-acetoxy-6-bromo-2-bromomethyl-1-methylindole-3-carboxylic acid through bromination reaction, (p-methyl isopropyl benzene)-rutheniumdichloride dimer is used as a catalyst, NBS serves as a bromination reagent, DMA serves as a solvent to replace a traditional bromine bromination reagent, reaction conditions are mild, reaction selectivity is high, raw material sources are convenient, pollution of bromine to the environment can be avoided, and the catalytic activity of the novel catalyst is not reduced due to the influence of thereaction environment. Therefore, the method has the advantages of few byproducts, high yield, low production cost, high safety, energy conservation and the like, and meets the modern chemical production requirements of green reaction.

ARBIDOL ANALOGS WITH IMPROVED INFLUENZA HEMAGGLUTININ POTENCY

The invention provides a series of analogs of arbidol having enhanced binding activity with respect to influenza hemagglutinin. Accordingly, the invention can provide a method of inhibiting the bioactivity of viral hemagglutinin activity, which is an essential step in the entry of infectious viral particles into host cells. The invention also can provide a method of treatment of influence, comprising administering an effective amount of a compound of formula (A), wherein X is S or O, to a patient afflicted therewith.