25015-91-2

Usage

Uses

Used in Pharmaceutical Industry:
2-bromo-2-5-dihydroxyacetophenone is used as a key intermediate for the synthesis of various medicinal compounds. Its unique structure allows it to participate in a wide range of reactions, such as nucleophilic substitution and Friedel-Crafts acylation, making it a valuable component in the development of new drugs.
Used in Organic Synthesis:
In the field of organic chemistry, 2-bromo-2-5-dihydroxyacetophenone is used as a versatile reagent for a variety of organic transformations. Its reactivity and compatibility with different reaction conditions make it an important building block for the synthesis of complex organic molecules.
Used in Fine Chemicals Industry:
2-bromo-2-5-dihydroxyacetophenone is also employed in the production of fine chemicals, where its unique properties contribute to the creation of high-quality specialty chemicals for various applications, including fragrances, dyes, and other chemical intermediates.

InChI:InChI=1/C8H7BrO3/c9-4-8(12)6-3-5(10)1-2-7(6)11/h1-3,10-11H,4H2

Upstream product

• 438239-21-5 1-(2,5-diacetoxy-phenyl)-2-diazo-ethanone 
• 598-21-0 2-Bromoacetyl bromide 
• 150-78-7 1,4-dimethoxybezene 
• 490-78-8 2,5-Dihydroxyacetophenone 
• 37785-02-7 2,5-diacetoxybenzoyl chloride 
• 1084-96-4 2,5-bis(acetyloxy)benzoic acid 

Downstream Products

• 408338-86-3 1-(5-acetoxy-2-hydroxy-phenyl)-2-bromo-ethanone 
• 408338-41-0 benzofuran-3,5-diol 
• 1003585-06-5 ethyl 2-(2,5-dihydroxyphenacyl)-3-oxobutanoate 
• 1003584-93-7 3-(2,5-dihydroxyphenacyl)pentane-2,4-dione 
• 1003585-24-7 diethyl 2-(2,5-dihydroxyphenacyl)propanedioate 
• 19278-82-1 5-hydroxy-2,3-dihydrobenzofuran-3-one 
• 1380075-00-2 N¹-4-chlorobenzylidene-N²-[3-(4-methoxyphenyl)-4-(2,5-dihydroxyphenyl)-1,3-thiazol-2-ylidene]hydrazine 
• 1380075-04-6 N¹-4-chlorobenzylidene-N²-[3-(4-hydroxy-3-methoxyphenyl)-4-(2,5-dihydroxyphenyl)-1,3-thiazol-2-ylidene]hydrazine 

Relevant academic research and scientific papers

Nucleus-independent chemical shift (NICS) as a criterion for the design of new antifungal benzofuranones

The assertion made by Wu et al. that aromaticity may have considerable implications for molecular design motivated us to use nucleus-independent chemical shifts (NICS) as an aromaticity criterion to evaluate the antifungal activity of two series of indol-4-ones. A linear regression analysis of NICS and antifungal activity showed that both tested variables were significantly related (p –1 for Candida glabrata, Candida krusei and Candida guilliermondii with compounds 15-32, 15-15 and 15-1. The MIC for filamentous fungi was 1.95 μg·mL–1 for Aspergillus niger for compounds 15-1, 15-33 and 15-34. The results obtained support the use of NICS in the molecular design of compounds with antifungal activity.

Design and synthesis of novel senkyunolide analogues as neuroprotective agents

A class of senkyunolide analogues bearing benzofuranone fragment were designed, synthesized and evaluated for their neuroprotective effect in models of oxygen glucose deprivation (OGD) and oxidative stress. All tested compounds showed neuroprotection profile based on the cell viability assay. In particular, derivatives 1f–1i possessing furoxan-based nitric oxide releasing functionality exhibited significant biological activities in OGD models. More importantly, compound 1g containing short linker with furoxan displayed the most potent neuroprotection at the concentration of 100 μM (cell survival up to 145.2%). Besides, 1g also showed the middle level neuroprotective effect in model of oxidative stress.

Ultrasounds-assisted synthesis of highly functionalized acetophenone derivatives in heterogeneous catalysis

A fast, general, environmentally friendly, and facile method for preparation of highly functionalized acetophenone derivatives under ultrasound irradiation in heterogeneous catalysis is presented. The ultrasound enhanced a remarkable rate of acceleration for bromination, the reaction time decrease significantly, reaction conditions are milder, the consumed energy decreases considerably and the amount of used solvents was reduced. Consequently, the ultrasounds-assisted bromination reaction could be considered ecofriendly. In the most cases under ultrasound irradiation the yields are higher, in some cases substantially. A comparative study, ultrasounds-conventional conditions was done.

Functionalized aurones as inducers of NAD(P)H:quinone oxidoreductase 1 that activate AhR/XRE and Nrf2/ARE signaling pathways: Synthesis, evaluation and SAR

The chemopreventive potential of functionalized aurones and related compounds as inducers of NAD(P)H:quinone oxidoreductase 1 (NQO1, EC 1.6.99.2) are described. Several 4,6-dimethoxy and 5-hydroxyaurones induced NQO1 activity of Hepa1c1c7 cells by 2-fold at submicromolar concentrations, making these the most potent inducers to be identified from this class. Mechanistically, induction of NQO1 was mediated by the activation of AhR/XRE and Nrf2/ARE pathways, indicating that aurones may be mixed activators of NQO1 induction or agents capable of exploiting the proposed cross-talk between the AhR and Nrf2 gene batteries. QSAR analysis by partial least squares projection to latent structures (PLS) identified size parameters, in particular those associated with non-polar surface areas, as an important determinant of induction activity. These were largely determined by the substitution on rings A and B. A stereoelectronic role for the exocyclic double bond as reflected in the E LUMO term was also identified. The electrophilicity of the double bond or its effect on the conformation of the target compound are possible key features for induction activity.

Synthesis of α-bromoalkanones using urea-hydrogen peroxide complex and sodium bromide over silica gel-acetic acid

α-Bromoalkanones 2 have been synthesized by the reaction of alkanones 1 with UHP-NaBr over SiO2-acetic acid in solvent-free conditions under microwave irradiation.

Montmorillonite K10 - AlCl3 catalyzed enolization: A bifunctional system for selective bromination of hydroxyacetophenones

A heterogeneous system consisting of montmorillonite K-10 and AlCl3 (catalytic amount) in ethyl acetate serves as an effective catalyst for the enolization of hydroxyacetophenones thereby facilitating selective bromination of side chain using molecular bromine.

Intramolecular weak hydrogen bonds in substituted 4-arylthiazoles

We have synthesized new polysubstituted 4-arylthiazoles with a substitution pattern able to form intramolecular weak hydrogen bonds as secondary structure, and besides, displaying in the aromatic region of their 1H-NMR spectra an ABX spin system and only one singlet (the thiazolic proton), thus permitting us to make doubtless assignments. These results confirmed previous assignments made by us in other thiazole-derivatives prepared by the first time. The spectroscopic data (IR, 1H-NMR and MS) of these thiazoles, as well as of the required intermediates, are discussed.