52727-99-8

Usage

Uses

Used in Pharmaceutical Research and Development:
2-BROMO-5'-CHLORO-2'-HYDROXYACETOPHENONE is used as a building block in the synthesis of various pharmaceuticals and biologically active molecules. Its unique structure allows for the creation of new compounds with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, 2-BROMO-5'-CHLORO-2'-HYDROXYACETOPHENONE serves as an important intermediate, facilitating the production of a wide range of chemical compounds.
Used in Materials Science:
2-BROMO-5'-CHLORO-2'-HYDROXYACETOPHENONE may also have applications in materials science, where its unique properties can contribute to the development of new materials with specific characteristics.
Used in Agrochemicals:
Additionally, 2-BROMO-5'-CHLORO-2'-HYDROXYACETOPHENONE could be utilized in the agrochemical industry, potentially leading to the development of new pesticides or other agricultural chemicals.

InChI:InChI=1/C8H6BrClO2/c9-4-8(12)6-3-5(10)1-2-7(6)11/h1-3,11H,4H2

Upstream product

• 1450-74-4 5-chloro-2-hydroxyacetophenone 
• 7789-45-9 copper(II)bromide 

Downstream Products

• 91515-90-1 2-(1H-pyrazol-1-yl)-2'-hydroxy-5'-chloroacetophenone 
• 80930-52-5 1-(5-chloro-2-hydroxyphenyl)-2-(1H-1-imidazolyl)-1-ethanone 
• 344444-91-3 1-(5-Chloro-2-hydroxy-phenyl)-2-(2-methyl-imidazol-1-yl)-ethanone 
• 52728-05-9 5'-Chlor-2,2'-dihydroxyacetophenon 
• 138206-81-2 1-[(E)-1-(5-Chloro-2-propoxy-phenyl)-2-methylsulfanyl-vinyl]-1H-imidazole 
• 138206-82-3 1-[(E)-1-(2-Butoxy-5-chloro-phenyl)-2-methylsulfanyl-vinyl]-1H-imidazole 
• 111809-39-3 1-[(E)-1-(5-Chloro-2-pentyloxy-phenyl)-2-methylsulfanyl-vinyl]-1H-imidazole 
• 138206-49-2 4-Chloro-2-((E)-1-imidazol-1-yl-2-methylsulfanyl-vinyl)-phenol 
• 138206-53-8 4-Chloro-2-((Z)-1-imidazol-1-yl-2-methylsulfanyl-vinyl)-phenol 
• 91515-91-2 3-(1H-pyrazol-1-yl)-3-<2-(2-hydroxy-5-chlorobenzoyl)-2-(1H-pyrazol-1-yl)>ethyl-6-chloro-2,3-dihydro-4H-1-benzopyran-4-one 
• 175655-05-7 2-(2-aminothiazol-4-yl)-4-chlorophenol 
• 167384-35-2 1-(5-Chloro-2-hydroxy-phenyl)-2-[tris-(4-chloro-phenyl)-λ⁵-phosphanylidene]-ethanone 

Relevant academic research and scientific papers

MeONH 2·hCl-Mediated α-Methylenation/Conjugate Addition of α-Sulfonylo-Hydroxyacetophenones with Methyl Sulfoxides: Route to 3-Sulfonylchroman-4-ones

A novel and efficient route for the synthesis of 3-sulfonylchroman-4-ones from α-sulfonyl o -hydroxyacetophenones with methyl sulfoxides via a MeONH 2·HCl-mediated sequential methylenation/ conjugate addition is described. Plausible reaction mechanisms are proposed and discussed. Various reaction conditions for this novel, one-pot, environmentally friendly conversion were investigated.

C-H bond cleavage-enabled aerobic ring-opening reaction of: In situ formed 2-aminobenzofuran-3(2 H)-ones

A C-H bond cleavage-enabled aerobic ring-opening reaction of 2-aminobenzofuran-3(2H)-ones formed in situ by hemiacetals with a variety of amines is reported. This simple one-pot reaction provides an alternative approach to obtain o-hydroxyaryl glyoxylamides in excellent yields of up to 97%. Alkylamines react with hemiacetals via a catalyst-free dehydration condensation to generate 2-aminobenzofuran-3(2H)-ones. The in situ formed semicyclic N,O-acetals undergo the same amine-initiated C-H bond hydroxylation in air under mild conditions to afford ring-opening products. Similarly, arylamines were investigated as substrates for a two-step tandem process involving a DPP-catalyzed condensation followed by a Et2NH-mediated C-H hydroxylation. Unlike the previously reported functionalization of N,O-acetals via a C-O or C-N cleavage, the aerobic oxidative C-H hydroxylation in this reaction, which is promoted by using stoichiometric amounts of alkylamines as both a Lewis base and a reductant at room temperature under atmospheric air, proceeds via α-carbonyl-stabilized carbanion intermediates from the C-H cleavage of N,O-acetals. This journal is

PdCl2/CuCl2/Bi(OTf)3-promoted Construction of Sulfonyl Dibenzooxabicyclo[3.3.1]nonanes and Arylnaphthalenes via Intramolecular Annulation of Sulfonyl o-Allylarylchromanones

PdCl2/CuCl2/Bi(OTf)3-promoted intramolecular domino annulation of sulfonyl o-allylarylchromanones provides tetracyclic sulfonyl dibenzooxabicyclo[3.3.1]nonanes and bicyclic arylnaphthalenes with good to excellent yields in MeOH at room (25 °C) and refluxing (65 °C) temperature, respectively. The starting sulfonyl o-allylarylchromanones can be easily obtained from the intermolecular cyclocondensation of α-sulfonyl o-hydroxyacetophenones and o-allylbenzaldehydes. The uses of various catalysts and solvent systems are investigated herein for convenient transformation. A plausible mechanism is proposed and discussed. This protocol provides one-pot ring closure via carbon-carbon (C?C) bond formation. (Figure presented.).

Temperature-Controlled Desulfonylative Condensation of α-Sulfonyl o-Hydroxyacetophenones and 2-Formyl Azaarenes: Synthesis of Azaaryl Aurones and Flavones

Temperature-controlled intermolecular desulfonylative condensation of α-sulfonyl o-hydroxyacetophenones with 2-formyl azaarenes (pyridines and quinolones) provides azaaryl (pyridyl and quinolyl) aurones and flavones under warming and refluxing toluene reaction conditions via the formation of the intermediate of sulfonyl chroman-4-one. The uses of various solvents are investigated for facile and efficient transformation. A plausible mechanism is proposed.

Discovery of clinical candidate (1 R,4 r)-4-((R)-2-((S)-6-Fluoro-5 H-imidazo[5,1-A[isoindol-5-yl)-1-hydroxyethyl)cyclohexan-1-ol (Navoximod), a potent and selective inhibitor of indoleamine 2,3-dioxygenase 1

A novel class of 5-substituted 5H-imidazo[5,1-a]isoindoles are described as potent inhibitors of indoleamine 2,3-dioxygenase 1 (IDO1). A structure-based drug design approach was used to elaborate the 5H-imidazo[5,1-a]isoindole core and to improve potency and pharmacological properties. Suitably placed hydrophobic and polar functional groups in the lead molecule allowed improvement of IDO1 inhibitory activity while minimizing off-target liabilities. Structure-activity relationship studies focused on optimizing IDO1 inhibition potency and a pharmacokinetic profile amenable to oral dosing while controlling CYP450 and hERG inhibitory properties.

Pyridine-substituted thiazolylphenol derivatives: Synthesis, modeling studies, aromatase inhibition, and antiproliferative activity evaluation

Drugs used in breast cancer treatments target the suppression of estrogen biosynthesis. During this suppression, the main goal is to inhibit the aromatase enzyme that is responsible for the cyclization and structuring of estrogens either with steroid or non-steroidal-type inhibitors. Non-steroidal derivatives generally have a planar aromatic structure attached to the triazole ring system in their structures, which inhibits hydroxylation reactions during aromatization by coordinating the heme group. Bioisosteric replacement of the triazole ring system and development of aromatic/cyclic structures of the side chain can increase the selectivity for aromatase enzyme inhibition. In this study, pyridine-substituted thiazolylphenol derivatives, which are non-steroidal triazole bioisosteres, were synthesized using the Hantzsch method, and physical analysis and structural determination studies were performed. The IC50 values of the compounds were determined by a fluorescence-based aromatase inhibition assay. Then, their antiproliferative activities on the MCF7 and HEK 293 cell lines were evaluated with the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Furthermore, the crystal structure of human placental aromatase was subjected to a series of docking experiments to identify the possible interactions between the most active structure and the active site. Lastly, an in silico technique was performed to analyze and predict the drug-likeness, molecular and ADME properties of the synthesized molecules.

Studies on non-steroidal inhibitors of aromatase enzyme; 4-(aryl/heteroaryl)-2-(pyrimidin-2-yl)thiazole derivatives

Steroidal and non-steroidal aromatase inhibitors target the suppression of estrogen biosynthesis in the treatment of breast cancer. Researchers have increasingly focused on developing non-steroidal derivatives for their potential clinical use avoiding steroidal side-effects. Non-steroidal derivatives generally have planar aromatic structures attached to the azole ring system. One part of this ring system comprises functional groups that inhibit aromatization through the coordination of the haem group of the aromatase enzyme. Replacement of the triazole ring system and development of aromatic/cyclic structures of the side chain can increase selectivity over aromatase enzyme inhibition. In this study, 4-(aryl/heteroaryl)-2-(pyrimidin-2-yl)thiazole derivatives were synthesized and physical analyses and structural determination studies were performed. The IC50 values were determined by a fluorescence-based aromatase inhibition assay and compound 1 (4-(2-hydroxyphenyl)-2-(pyrimidine-2-yl)thiazole) were found potent inhibitor of enzyme (IC50:0.42 nM). Then, their antiproliferative activity over MCF-7 and HEK-293 cell lines was evaluated using a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Compounds 1, 7, 8, 13, 15, 18, 21 were active against MCF-7 breast cancer cells. Lastly, a series of docking experiments were undertaken to analyze the crystal structure of human placental aromatase and identify the possible interactions between the most active structure and the active site.

SUBSTITUTED CARBONUCLEOSIDE DERIVATIVES USEFUL AS ANTICANCER AGENTS

Compounds of the general formula:processes for the preparation of these compounds, compositions containing these compounds, and the uses of these compounds.

Tuning of excited-state intramolecular proton transfer (ESIPT) fluorescence of imidazo[1,2-a]pyridine in rigid matrices by substitution effect

2-(2′-Hydroxyphenyl)imidazo[1,2-a]pyridine (HPIP, 1) and its derivatives are synthesized, and their fluorescence properties are studied. Although all the compounds show faint dual emission (Φ ≈ 0.01), which is assigned to the normal and excited-state intr

Photochemical α-bromination of ketones using N-bromosuccinimide: a simple, mild and efficient method

Aromatic and aliphatic carbonyl compounds undergo facile bromination with N-bromosuccinimide under UV-vis irradiation to give the corresponding α-brominated ketones in good yields, at low temperatures (30 °C), without any catalyst, catalyst support or radical initiator and within a short time.