22362-66-9

Usage

Uses

3'',5''-Dibromo-2''-hydroxyacetophenone is a useful reagent in organic synthesis.

Preparation

Preparation by Fries rearrangement of 2,4-dibromophenyl acetate with aluminium chloride without solvent between 150° and 165°.

Upstream product

• 615-58-7 2,4-dibromophenol 
• 108-24-7 acetic anhydride 
• 7446-70-0 aluminium trichloride 
• 36914-79-1 acetic acid 2,4-dibromophenyl ester 
• 108-95-2 phenol 
• 118-93-4 o-hydroxyacetophenone 
• 1450-75-5 5-Bromo-2-hydroxyacetophenone 
• 98436-51-2 2,2,2-tribromo-1-(3,5-dibromo-2-hydroxyphenyl)ethanone 

Downstream Products

• 24539-95-5 2,4-dibromo-6-ethylphenol 
• 789-81-1 (E)-N′-[1-(2-hydroxyphenyl)ethyliden]isonicotinoylhydrazide 
• 134640-62-3 2-Methoxy-benzoic acid 2-acetyl-4,6-dibromo-phenyl ester 
• 153449-98-0 4-Nitro-benzoic acid 2-acetyl-4,6-dibromo-phenyl ester 
• 75768-01-3 (E)-3-(4-Chloro-phenyl)-1-(3,5-dibromo-2-hydroxy-phenyl)-propenone 
• 288399-84-8 6,8-dibromo-4-hydroxy-1-benzopyran-2-one 
• 101602-26-0 3,5-dibromo-3,4-dimetoxy-2-hydroxy-chalcone 
• 92832-04-7 3',5'-dibromo-2'-hydroxyacetophenone imine 
• 1198475-10-3 6,8-dibromo-2-(4-fluorophenyl)-4H-chromen-4-one 
• 1609456-14-5 6,8-dibromo-2-(3,4-dihydroxyphenyl)-4H-chromen-4-one 
• 1609456-17-8 6,8-diamino-2-(3,4-dihydroxyphenyl)-4H-chromen-4-one 
• 1609456-20-3 6,8-dibromo-3-hydroxy-2-(3-methoxy-4-(methoxymethoxy)phenyl)-4H-chromen-4-one 
• 1609456-21-4 2-(3,4-bis(methoxymethoxy)phenyl)-6,8-dibromo-3-hydroxy-4H-chromen-4-one 
• 1417634-86-6 6,8-dibromo-3-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one 

Relevant academic research and scientific papers

OXADIAZOLE AND PHENOL DERIVATIVES AS ANTIBACTERIAL AND/OR HERBICIDAL AGENTS

Antimicrobial resistance is rising at an alarming rate. The methylerythritol phosphate (MEP) pathway is a metabolic pathway that produces the isoprenoids isopentyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP). Notably, the MEP pathway is present in bacteria and not mammals, which made the enzymes of the MEP pathway attractive targets for discovering new anti-infective agents due to reduced chances of off-target interactions leading to side effects. The biophysical properties of 2-C-methyl-D-erythritol 4-phosphate cytidylyltransferase (IspD) and 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase (IspE) were determined to aid discovery of novel inhibitors. Thermal shift screening was used as an initial filter to narrow down a library of compounds with thermal shifts greater than 1° C., which could indicate binding to the IspD and IspE enzymes. Follow-up studies were performed using isothermal titration calorimetry and enzymatic inhibition assays. Results from these studies have revealed compounds with high micromolar inhibition of both IspD from Escherichia coli and IspE from Burkholderia thailandensis. The hit compounds are used for future development of more potent IspD and IspE inhibitors.

Regioselective monobromination of aromatics via a halogen bond acceptor-donor interaction of catalytic thioamide and N-bromosuccinimide

Regioselective monobromination of various aromatics was achieved at room temperature using N-bromosuccinimide and 5 mol% of thioamides in acetonitrile. With thiourea as catalyst, activated aromatics, such as anisole, acetanilide, benzamide and phenol analogues containing electron donating or withdrawing groups, were brominated with high regioselectivity. Room temperature brominations of weakly activated aromatics and deactivated 9-fluorenone were accomplished by 5 mol% thioacetamide, higher substrates concentrations and longer reaction times. A backbonding of the bromine lone pairs with the π*of C[dbnd]S group and a halogen bond between the halogen bond donor bromine and the halogen bond acceptor sulfur of the thioamide are thought to be the principal interactions and cause of N-bromosuccinimide activation.

synthesis of some 4-methyl-2-(3-methylbenzofuran-2- yl)quinoline -3-carboxylic acids

In the present investigation, one-pot synthetic route for the synthesis of 4-methyl-2-(3- methylbenzofuran-2-yl)quinoline-3-carboxylic acids 3a-f has been described, involving the reaction of ethyl 2- (chloromethyl)-4-methylquinoline-3-carboxylate (1) with various 1-(2-hydroxyphenyl)ethanones 2a-f in refluxing MeCN with the presence of K2 CO3 as base and PEG-400 as phase transfer catalyst. The structures of all the newly- 2 3 synthesized compounds were confirmed by IR, 1H NMR, 13C NMR and HRMS.

Site-Selective Suzuki-Miyaura Reaction of 6,8-Dibromoflavone

8-Aryl- and 6,8-diarylflavones were prepared by Suzuki-Miyaura reactions of 6,8-dibromoflavone. In spite of the greater steric hindrance, the first attack proceeded with good site selectivity at position 8.

Cu-Mn spinel oxide catalyzed regioselective halogenation of phenols and N-heteroarenes

A novel simple, mild chemo- and regioselective method has been developed for the halogenation of phenols using Cu-Mn spinel oxide as a catalyst and N-halosuccinimide as halogenating agent. In the presence of Cu-Mn spinel oxide B, both electron-withdrawing and electron-donating groups bearing phenols gave monohalogenated products in good to excellent yields with highest para-selectivity. The para-substituted phenol gave monohalogenated product with good yield and ortho-selectivity. N-Heteroarenes such as indoles and imidazoles also gave monohalogenated products with high selectivity. Unlike the copper-catalyzed halogenation, the present method works well with electron-withdrawing group bearing phenols and gives comparatively better yields and selectivity. The Cu-Mn spinel catalyst is robust and reused three times under optimized conditions without any loss in catalytic activity. Nonphenolics did not undergo this transformation.

Reaction of 4-(2′-hydroxyaryl)-1,3-dithiolium salts with sodium sulfide. A selective synthesis of 2′-hydroxyacetophenones

The treatment of 4-(2′-hydroxyaryl)-2-(N,N-dialkylamino)-1,3-dithiolium perchlorates (1a-g) with sodium sulfide nonahydrate in ethanol at room temperature affords the corresponding 1,3-dithiole-2-thiones (2a-g). When these reactions are conducted in boiling ethanol, 2′-hydroxyacetophenones (3a-g) have been obtained in good to excellent yield. A tentative mechanism for the formation of 3a-g shows that this reaction is regioselective, this being established by the presence of hydroxyl group in 2′-position. That has been confirmed in a control experiment, 4-phenyl-2-(piperidin-1-yl)-1,3-dithiolium perchlorate affording a mixture of condensation products of acetophenone and phenylacetaldehyde, under similar reaction conditions.

Pyridinium bromochromate: A new and efficient reagent for bromination of hydroxy aromatics

Pyridinium bromochromate (PBC) has been used as an efficient and selective nuclear brominating agent for bromination of various substituted hydroxy-acetophenones, aldehydes and phenols.

Substituted alkylaryl ketones and methods of use as herbicides

Ring and side chain substituted alkylaryl ketones are useful in controlling the growth of germinating and seedling weed grasses and germinating and seedling broadleaf weeds.