182056-48-0

Basic information

• Product Name: ETHANONE, 1-(5-BROMO-2,4-DIMETHOXYPHENYL)
• Synonyms: ETHANONE, 1-(5-BROMO-2,4-DIMETHOXYPHENYL);1-(5-bromo-2,4-dimethoxyphenyl)ethan-1-one
• CAS NO: 182056-48-0
• Molecular Formula: C₁₀H₁₁BrO₃
• Molecular Weight: 259.1
• Mol File: 182056-48-0.mol
• Article Data: 10

Chemical Properties

• Melting Point: 149–150°C
• Appearance: /
• CAS DataBase Reference: ETHANONE, 1-(5-BROMO-2,4-DIMETHOXYPHENYL)(CAS DataBase Reference)
• NIST Chemistry Reference: ETHANONE, 1-(5-BROMO-2,4-DIMETHOXYPHENYL)(182056-48-0)
• EPA Substance Registry System: ETHANONE, 1-(5-BROMO-2,4-DIMETHOXYPHENYL)(182056-48-0)

Safety Data

• Hazardous Substances Data: 182056-48-0(Hazardous Substances Data)

Usage

Preparation

Obtained by reaction of acetic anhydride with 1-bromo-2,4-dimethoxybenzene in the presence of boron trifluoride etherate in methylene chloride first at 0°, then at r.t. for 24 h (85%).

Upstream product

• 77-78-1 dimethyl sulfate 
• 829-20-9 2',4'-dimethoxyacetophenone 
• 17715-69-4 1-Bromo-2,4-dimethoxybenzene 
• 108-24-7 acetic anhydride 

Downstream Products

• 958453-93-5 1-(2,4-dimethoxy-5-(4-(piperidin-1-yl)piperidin-1-yl)phenyl)ethanone 
• 958453-90-2 1-[2,4-dimethoxy-5-(4-methylpiperazin-1-yl)phenyl]ethanone 
• 1228275-92-0 2-(5-bromo-2,4-dimethoxyphenyl)-2,4,5-trimethyl-1,3-dioxolane 
• 1177256-05-1 6-(3-chloro-2-fluorobenzyl)-1-((2R)-1-hydroxy-3-methylbutan-2-yl)-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 
• 1171823-92-9 (S)-ethyl 3-(1-hydroxy-3-methylbutan-2-ylamino)-2-(5-bromo-2,4-dimethoxybenzoyl)acrylate 
• 1171823-91-8 ethyl 2-(5-bromo-2,4-dimethoxybenzoyl)-3-(dimethylamino)acrylate 
• 99359-58-7 1-bromo-5-(1-bromo-ethyl)-2,4-dimethoxy-benzene 
• 154377-22-7 5-bromo-2,4-dimethoxyphenol 
• 20129-11-7 1-bromo-2,4,5-trimethoxybenzene 
• 19345-66-5 1-bromo-5-ethyl-2,4-dimethoxybenzene 
• 855629-88-8 1-acetoxy-5-bromo-2,4-dimethoxy-benzene 
• 1598387-97-3 (R)-methyl 3-(1-hydroxy-3-methylbutan-2-ylamino)-2-(5-bromo-2,4-dimethoxybenzoyl)acrylate 
• 697761-98-1 elvitegravir 

Relevant articles and documents

ROR-GAMMA INHIBITORS

The present invention relates to compounds of formula I and pharmaceutical compositions comprising compounds of formula I. Compounds of Formula I are useful in treatment of inflammatory, metabolic or autoimmune diseases which are mediated by RORy.

An Improved Synthesis of Elvitegravir

An improved process for the active pharmaceutical ingredient of a new HIV integrase inhibitor elvitegravir (1) has been developed. It starts from commercially available 2,4-dimethoxyacetophenone, which is selectively halogenated into the position 5. The 5-halo acetophenones are condensed with dialkyl carbonates to give the corresponding benzoylacetates. Their treatment with N,N-dimethylformamide dimethyl acetal followed by (S)-valinol then provided the corresponding intermediate benzoyl acrylates. Cyclization to the required 1,4-dihydroquinolin-4-oxo derivatives by aromatic nucleophilic substitution of the 2-methoxy group was achieved by treatment with N,O-bis(trimethylsilyl)-acetamide, which also protected the OH group as the trimethylsilyl derivative. Finally, the Negishi coupling with 2-fluoro-3-chlorobenzylzinc bromide and the following hydrolysis provided elvitegravir (1). The preferred variant, the seven-step procedure starting from 2,4-dimethoxyacetophenone, provides elvitegravir in 29.3% yield.

Total synthesis, antiprotozoal and cytotoxicity activities of rhuschalcone VI and analogs

The total synthesis of a potent antiplasmodial natural bichalcone, rhuschalcone VI, is described starting from simple and available resorcinol and 4-hydroxybenzaldehyde. Key steps include the solvent-free Aldol syntheses of chalcones, and the successful application of the Suzuki-Miyaura coupling reaction in the synthesis of bichalcones. The present work constitutes a general method for the rapid syntheses of a number of bichalcones related to rhuschalcone VI. Some of the bichalcones showed moderate antiprotozoal activities against Bodo caudatus, a preliminary screening system for antitrypanosomal activities, most of them with little or no cytotoxicity.