28480-70-8

Usage

Uses

Used in Pharmaceutical Industry:
5'-Chloro-2'-hydroxy-4'-methylacetophenone is used as a key intermediate compound for the synthesis of chalcones, which are essential in the preparation of novel pyrazoline derivatives. These derivatives have potential applications in the development of new pharmaceuticals due to their diverse biological activities.
Used in Chemical Synthesis:
In the field of chemical synthesis, 5'-chloro-2'-hydroxy-4'-methylacetophenone serves as a starting material for the preparation of various complex organic compounds, such as 5'-chloro-2'-hydroxy-4'-methyl-3-(2''-thienyl)acrylophenone and 6-chloro-3-hydroxy-7-methyl-2-(2-thienyl)-4H-chromen-4-one. These compounds can be further utilized in the development of new materials and chemicals with specific properties and applications.
Used in Analytical Chemistry:
5'-Chloro-2'-hydroxy-4'-methylacetophenone is also used as a complexing agent in the spectrophotometric determination of vanadium(V). This application is crucial in analytical chemistry for the accurate measurement and analysis of vanadium concentrations in various samples, such as environmental, geological, and industrial materials.

Preparation

Preparation by reaction of acetic acid on 4-chloro-3- methylphenol with boron trifluoride at 70–100° (80–85%).

Upstream product

• 54963-43-8 4-chloro-3-methylphenyl acetate 
• 59-50-7 4-Chloro-3-methylphenol 
• 64-19-7 acetic acid 
• 38589-71-8 5-chloro-2-hydroxy-4-methyl-acetophenone oxime 
• 75-36-5 acetyl chloride 
• 5903-07-1 4-chloro-2-isopropyl-5-methyl-anisole 

Downstream Products

• 18980-09-1 6-Ethyl-3-methyl-p-Chlorophenol 
• 141213-82-3 (E)-1-(5-Chloro-2-hydroxy-4-methyl-phenyl)-3-(2-methoxy-naphthalen-1-yl)-propenone 
• 146517-65-9 (E)-1-(5-Chloro-2-hydroxy-4-methyl-phenyl)-3-(4-chloro-naphthalen-1-yl)-propenone 
• 141213-81-2 (E)-1-(5-Chloro-2-hydroxy-4-methyl-phenyl)-3-naphthalen-1-yl-propenone 
• 1026-32-0 (2-acetyl-4-chloro-5-methylphenoxy)acetic acid ethyl ester 
• 292144-86-6 1-(5-chloro-2-hydroxy-3-iodo-4-methylphenyl)ethan-1-one 
• 41082-32-0 (E)-1-(5-Chloro-2-hydroxy-4-methyl-phenyl)-3-(2-hydroxy-phenyl)-propenone 
• 24547-66-8 (E)-1-(5-Chloro-2-hydroxy-4-methyl-phenyl)-3-p-tolyl-propenone 
• 41011-08-9 2'-hydroxy-4'-methyl-5'-chlorochalcone 
• 837416-51-0 3-(1-phenyl-3-thiophen-2-yl-1H-pyrazol-4-yl)-acrylic acid 2-acetyl-4-chloro-5-methyl-phenyl ester 
• 778639-52-4 2-methyl-4-nitro-5-propyl-2H-pyrazole-3-carboxylic acid 2-acetyl-4-chloro-5-methyl-phenyl ester 
• 147919-55-9 6-Chloro-7-methyl-2-phenyl-chroman-4-one 
• 24547-65-7 (E)-1-(5-Chloro-2-hydroxy-4-methyl-phenyl)-3-(4-methoxy-phenyl)-propenone 
• 203301-18-2 4-chloro-2-(1-hydrazono-ethyl)-5-methyl-phenol 

Relevant academic research and scientific papers

Synthesis and Antibacterial Screening of Some New Pyrazolylchromones and Pyrazolylcoumaran-3-ones

Some new pyrazolylchromones 4a-e (flavone analogs) and pyrazolylcoumaran-3-ones 5a-e (aurone analogs) were synthesized by refluxing chalcones 3a-e in dimethyl sulfoxide/I2 and Pyridine/ Hg(OAc)2, respectively. Spectral techniques such as infrared, proton nuclear magnetic resonance, and mass spectrometry were used to confirm the structures of newly synthesized compounds. These compounds were studied for their antibacterial activities toward Bacillus subtilis, Staphylococcus aureus, Escherichia coli, and Salmonella typhi. Some of these compounds showed promising activity against test organisms.

Ultrasound-assisted synthesis and antimicrobial activity of tetrazole-based pyrazole and pyrimidine derivatives

New tetrazole-based pyrazole and pyrimidine derivatives were synthesized by an ultrasound irradiation method. All compounds were characterized by infrared spectroscopy (IR), 1H nuclear magnetic resonance (NMR), 13C NMR, mass spectrometry (MS) and elemental analysis and assessed in vitro for their efficacy as antimicrobial agents against four bacteria (Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Pseudomonas aeruginosa) and two fungi (Candida albicans, Aspergillus Niger). Compounds 8a, 8e, 9a, 9b and 9e show potent activity against the tested strains compared to the reference drugs chloramphenicol and clotrimazole.

Synthesis, antimicrobial activity and anti-biofilm activity of novel tetrazole derivatives

In the development of antimicrobial agents, we designed and synthesized novel tetrazole derivatives. The structures of compounds 6a-f and 7a-f were characterized by IR, 1H NMR, 13C NMR, MS and elemental analysis. These compounds were tested for their antimicrobial activity against a series of strains Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa and for antifungal activity against the strains Candida albicans, Candida glabrata, and Candida tropicalis. Compounds 6e, 6f, 7a, and 7f exhibit potent antimicrobial activities compared to the reference drugs streptomycin and miconazole. Tetrazole derivatives 7a-f also inhibit biofilm formation and compound 7f exhibits best anti-biofilm activity with a biofilm inhibitory concentration (BIC) as low as 0.9 μm.

Photochemistry of aroyloxiranes: Substituent effect on oxepinones and hydroxyalkenones formation

The photo-irradiation of some aroyloxiranes with Pyrex filtered UV-light from 125?W medium pressure Hg lamp has been described. These compounds furnished the 2-aryl-4,10-dihydrofuro[3,2-c][1]benzoxepin-10-ones and the hydroxyalkenones by the photochemical irradiation. The product(s) formation/distribution in terms of oxepinones and the hydroxyalkenones largely depended upon the nature of the substituent: the oxiranes having electron-donating groups in their benzoyl moiety gave the hydroxyalkenones while oxiranes having electron-withdrawing groups furnished the oxepinones as the major products. The formation of oxepinones has been envisaged to occur through the heterolytic [Formula presented] bond cleavage of epoxide to give carbonyl ylide intermediates followed by the furo-oxepinone ring formation via [3+2] cycloaddition and of hydroxyalkenones through the initial β-H abstraction followed by epoxide ring opening. The structures of all the compounds (substrates and photoproducts) have been determined on the basis of their spectral data (IR, NMR and Mass).

Synthesis of hydrazones schiff bases and microbiological evaluation of lsonicotinoyl hydrazide with different acetophenone

A series of hydrazones Schiff bases compounds have been synthesized by reacting isonicotinoyl hydrazide with 2-hydroxy-5-chloro acetophenone, 2-hydroxy-5-methyl acetophenone, 2-hydroxy-5-carboxy acetophenone, 2,5-dihydroxy acetophenone, 2-hydroxy-5-chloro-4-methyl acetophenone, 2-hydroxy-5-chloro-3- nitro acetophenone, 2-hydroxy-5-methyl-3-nitro acetophenone and 2-hydroxy-5-bromo acetophenone. The Schiff bases have been evaluated for the antifungal and antibacterial activities.

Use of 4-cyanocoumarins as dienophiles in a facile synthesis of highly substituted dibenzopyranones

(Chemical Equation Presented) A new synthesis of dibenzopyranones 14 is reported via the Diels-Alder cycloaddition of 4-cyanocoumarins 12 with 1-silyloxydienes 10 to give the adducts 13 which are then converted into 14 in one step via treatment with base and loss of the cyano and silyloxy groups.

Synthesis and evaluation of [2-(4-quinolyloxy)phenyl]methanone derivatives: Novel selective inhibitors of transforming growth factor-β kinase

We synthesized and evaluated various [2-(4-quinolyloxy)phenyl]methanone derivatives. These compounds had novel chemical structures that were distinct from those of previously reported inhibitors. Biological data suggested that these compounds inhibited transforming growth factor-β signaling by interacting with the ATP-binding pocket of the transforming growth factor-β type I receptor kinase domain. Here, we report on the synthesis and structure-activity relationships of the compounds in this series.

Identification of anthranilic acid derivatives as a novel class of allosteric inhibitors of hepatitis C NS5B polymerase

A series of potent anthranilic acid-based inhibitors of the hepatitis C NS5B polymerase has been identified. The inhibitors bind to a site on NS5B between the thumb and palm regions adjacent to the active site as determined by X-ray crystallography of the enzyme-inhibitor complex. Guided by both molecular modeling and traditional SAR, the enzyme activity of the initial hit was improved by approximately 100-fold, yielding a series of potent and selective NS5B inhibitors with IC50 values as low as 10 nM. These compounds were also inhibitors of the HCV replicon in cultured HUH7 cells.

QSAR studies of paeonol analogues for inhibition of platelet aggregation

Various paeonol analogues were synthesized and tested in vitro as inhibitors of platelet aggregation. Structural properties (or descriptors) of paeonol analogues were calculated and the structure-activity relationships were determined. Several multiple linear and nonlinear regression models and back-propagation neural network model were tested and the latter using relative positive charge, hydration energy, and hydrophilic factor as inputs gave the best data fitting with R2 = 0.89 and qpre2=0.66. The correlation coefficient between antiplatelet inhibition activity with an interaction energy between the paeonol compounds with COX-1 enzyme is only 0.39.

Synthesis of some benzothiazepins and their antimicrobial activities

A series of 2-[(substitutedphenyl)-4-(substitutedphenyl)]-3,3-dihydro substituted-1,5-benzothiazepin 3 has been synthesized starting from acetophenones. The compounds are characterized and screened for their antimicrobial activities.