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

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

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

Downstream Products

• 855629-88-8 1-acetoxy-5-bromo-2,4-dimethoxy-benzene 
• 19345-66-5 1-bromo-5-ethyl-2,4-dimethoxybenzene 
• 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 
• 20129-11-7 1-bromo-2,4,5-trimethoxybenzene 
• 154377-22-7 5-bromo-2,4-dimethoxyphenol 
• 99359-58-7 1-bromo-5-(1-bromo-ethyl)-2,4-dimethoxy-benzene 
• 1228275-92-0 2-(5-bromo-2,4-dimethoxyphenyl)-2,4,5-trimethyl-1,3-dioxolane 
• 1598387-86-0 methyl 3-(5-bromo-2,4-dimethoxyphenyl)-3-oxopropanoate 
• 1598387-89-3 methyl 2-(5-bromo-2,4-dimethoxybenzoyl)-3-(dimethylamino)acrylate 
• 1598387-92-8 (S)-methyl 3-(1-hydroxy-3-methylbutan-2-ylamino)-2-(5-bromo-2,4-dimethoxybenzoyl)-acrylate 
• 697761-98-1 elvitegravir 
• 1598387-97-3 (R)-methyl 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 

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.

BICYCLIC COMPOUND AND USE THEREOF FOR INHIBITING SUV39H2

The present invention directs to a compound represented by formula (I).

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.

A NEW PRODUCTION METHOD AND NEW INTERMEDIATES OF SYNTHESIS OF ELVITEGRAVIR

The present solution relates to an improved production method of elvitegravir of formula I, which is being clinically evaluated for treatment of HIV infection. Elvitegravir of formula I is produced via the intermediate of formula II, the preparation of which is also an object of the present solution.

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.

A new method for halogenation of aromatic compounds by using dimethyldioxirane and tetrabutylammonium halides

In this presentation the novel regioselective halogenation of arenes or phenols with dimethyldioxirane and Bu4NX is described. The results showed that a new, versatile and mild method can be utilized for preparation of aryl halides starting with arenes or phenols. Finally, this aryl halide forming methodology is applicable to structurally more complex flavonoids.

Halogenation of ketones with N-halosuccinimides under solvent-free reaction conditions

Several aryl substituted ketones, cyclic ketones, 1,3-diketones and a β-ketoamide were halogenated with N-halosuccinimides under solvent-free reaction conditions (SFRC) at various temperatures (20-80 °C), whereas less enolized ketones required the presence of an acid catalyst (p-toluenesulfonic acid, PTSA). Bromination of substituted acetophenones obeys first order kinetics v=kBr[ketone] and the following correlation with the keto-enol equilibrium constant: log kBr=0.3pKE+C1, less enolized substrates being more reactive; the moderate positive charge developed in the rate determining step was confirmed by the Hammett correlation (ρ=-0.5). On the other hand, in cyclic ketones an opposite relation was observed: log kBr=-0.6pKE+C2, indicating higher reactivity of substrates with higher enolization constant (KE). The important role of the nature of the solvent (MeCN, MeOH) in preorganization of the ketone-NBS-PTSA mixture prior to SFRC bromination was found.

Antiproliferative activity of chalcones with basic functionalities

A library of chalcones with different basic groups were synthesized and evaluated for antiproliferative activities against the human breast cancer (MCF 7) and colon cancer (HCT 116) cell lines. Structure-activity relationships were analyzed by projection

Directed regioselectivity of bromination of ketones with NBS: solvent-free conditions versus water

The reaction conditions employed directed the site of functionalisation of ketones with NBS: under solvent-free conditions α-bromination was the exclusive process, while in water, ring functionalisation occurred in the case of methoxy substituted aromatic ketones.

The Bromination of Phenolic Methyl Ethers with Hydrogen Bromide using Sodium Tungstate and Hydrogen Peroxide as Oxidant

Sodium tungstate has been found to be an effective catalyst for the nuclear bromination of some aromatic methyl ethers using hydrogen bromide in glacial acetic acid and hydrogen peroxide as the oxidant.