3226-34-4

Usage

Uses

Used in Organic Synthesis:
1-(3-CHLORO-2-HYDROXYPHENYL)ETHAN-1-ONE is used as a synthetic intermediate for the production of various organic compounds. Its unique structure allows it to be a versatile building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-(3-CHLORO-2-HYDROXYPHENYL)ETHAN-1-ONE is used as a key intermediate in the development of new drugs. Its chemical properties make it a valuable component in the synthesis of molecules with potential therapeutic applications.
Used in Agrochemical Industry:
1-(3-CHLORO-2-HYDROXYPHENYL)ETHAN-1-ONE is also utilized in the agrochemical industry for the synthesis of compounds with pesticidal properties. Its incorporation into these molecules can enhance their effectiveness in controlling pests and diseases in agriculture.
Used in Dye and Pigment Industry:
In the dye and pigment industry, 1-(3-CHLORO-2-HYDROXYPHENYL)ETHAN-1-ONE is used as a starting material for the production of various dyes and pigments. Its yellow color and chemical reactivity make it suitable for creating a range of colored compounds used in various applications, such as textiles, plastics, and inks.

Preparation

Preparation by Fries rearrangement of 2-chlorophenyl acetate with aluminium chloride,without solvent, between 110° and 180° (40–21%)in tetrachloroethane at 70–80°.

InChI:InChI=1/C8H7ClO2/c1-5(10)6-3-2-4-7(9)8(6)11/h2-4,11H,1H3

Upstream product

• 118-93-4 o-hydroxyacetophenone 
• 95-57-8 2-monochlorophenol 
• 4525-75-1 2-chlorophenyl acetate 
• 99-02-5 3'-Chloroacetophenone 
• 725718-12-7 3-chloro-2-methoxylbenzonitrile 
• 99585-09-8 2-chloro-6-acetylphenyl methyl ether 
• 87428-45-3 2-hydroxy-m-chloroacetophenone ethoxycarbonylhydrazone 
• 75-36-5 acetyl chloride 
• 42524-22-1 3-chloro-2-hydroxyacetophenone oxime 

Downstream Products

• 6077-14-1 3'-chloro-2,2'-dihydroxy-trans-chalcone 
• 101726-82-3 7-chloro-3-methyl-2-benzofuryl phenyl ketone 
• 96755-01-0 1-(3-chloro-2-hydroxyphenyl)-3-(6-benzodioxan-1,4-yl)propenone 
• 127245-60-7 ethyl 2-(2-acetyl-6-chlorophenoxy)propionate 
• 778639-42-2 2-methyl-5-propyl-2H-pyrazole-3-carboxylic acid 2-acetyl-6-chloro-phenyl ester 
• 1353024-73-3 C₁₆H₁₃ClO₃ 
• 1354928-55-4 C₁₇H₁₁ClO₄ 
• 1354928-60-1 C₁₇H₁₁ClO₄ 
• 99585-09-8 2-chloro-6-acetylphenyl methyl ether 
• 104971-95-1 (E)-1-(3-Chloro-2-hydroxy-phenyl)-3-(5-nitro-furan-2-yl)-propenone 

Relevant academic research and scientific papers

Novel p-functionalized chromen-4-on-3-yl chalcones bearing astonishing boronic acid moiety as MDM2 inhibitor: Synthesis, cytotoxic evaluation and simulation studies

Background: Novel 4-[3-(6/7/8-Substituted 4-Oxo-4H-chromen-3-yl)acryloyl]phenyl-boronic acid derivatives (5a-h) as well as other 6/7/8-substituted-3-(3-oxo-3-(4-substituted-phenyl)prop-1-enyl)-4H-chromen-4-one derivatives (3a-u) have been designed as p53-MDM2 pathway inhibitors and reported to possess significant cytotoxic properties against several cancer cell lines. Objectives: The current project aims to frame the structure-anticancer activity relationship of chromen-4-on-3-yl chalcones (3a-u/5a-h). In addition, docking studies were performed on these chromeno-chalcones in order to have an insight into their interaction possibilities with MDM2 pro-tein. Methods: Twenty-nine chromen-4-on-3-yl chalcone derivatives (3a-u/5a-h) were prepared by utilizing silica supported-HClO4 (green route with magnificent yield) and tested against four cancer cell lines (HCT116, MCF-7, THP-1, NCIH322). Results: Among the series 3a-u, compound 3b exhibited the highest anticancer activity (with IC50 values ranging from 8.6 to 28.4 μM) overall against tested cancer cell lines. Interestingly, para-Boronic acid derivative (5b) showed selective inhibition against colon cancer cell line, HCT-116 with an IC50 value of 2.35 μM. Besides the emblematic hydrophobic interactions of MDM2 inhibi-tors, derivative 5b was found to exhibit extra hydrogen bonding with GLN59 and GLN72 residues of MDM2 in molecular dynamics (MD) simulation. All the compounds were virtually nontoxic against normal fibroblast cells. Conclusion: Novel compounds were obtained with good anticancer activity especially 6-Chlorochromen-4-one substituted boronic acid derivative 5b. The molecular docking study proposed good activity as a MDM-2 inhibitor suggesting hydrophobic as well as hydrogen bonding interactions with MDM2.

Hydroximoyl-tetrazole derivative fungicide

The invention provides a hydroximoyl-tetrazole derivative fungicide, and particularly relates to hydroximoyl-tetrazole derivative, a preparing method thereof, application of hydroximoyl-tetrazole derivative serving as a fungicidal active agent, a form of

Total Synthesis and Structure Revision of Palmarumycin B6

Palmarumycin B6 and its regioisomer were synthesized via 7- and 13-step routes using 2-chlorophenol and 4-chlorophenyl methyl ether as the starting materials in overall yields of 2.7% and 12%, respectively. Their structures were characterized b

Photocatalytic benzene and benzene derivative direct hydroxylation or amination method

The invention discloses a photocatalytic benzene and benzene derivative direct hydroxylation or amination method. The method is characterized by comprising the following steps: (1) adding a photo-sensitizer and a cobalt catalyst into a solvent to obtain a solution (A); (2) adding benzene (or benzene derivatives), water, ammonia gas, and amide derivatives (or sulfonamide derivatives) into the solution (A) to obtain a solution (B); and (3) in a N2 (or Ar) environment, radiating the solution (B) by a medium pressure mercury lamp, a high pressure mercury lamp, a xenon lamp, or an LED lamp to obtain phenols or amines and H2. For the first time, a photo-sensitizer and a cobalt catalyst are combined and applied to photocatalytic hydroxylation and amination of benzene. The conditions of the method are mild, light is taken as the driving energy, no oxidant is added, the only byproduct is H2, and the whole process is green, concise, and efficient. High selective benzene one-step hydroxylation to generate phenol or high selective phenol/benzene one-step amination to generate aniline is realized, and the method can be applied to the production of phenol and aniline.

Synthesis and biological evaluation of phenoxyacetic acid derivatives as novel free fatty acid receptor 1 agonists

Free fatty acid receptor 1 (FFA1) is a new potential drug target for the treatment of type 2 diabetes because of its role in amplifying glucose-stimulated insulin secretion in pancreatic β-cell. In the present studies, we identified phenoxyacetic acid derivative (18b) as a potent FFA1 agonist (EC50 = 62.3 nM) based on the structure of phenylpropanoic acid derivative 4p. Moreover, compound 18b could significantly improve oral glucose tolerance in ICR mice and dose-dependently reduced glucose levels in type 2 diabetic C57BL/6 mice without observation of hypoglycemic side effect. Additionally, compound 18b exhibited acceptable PK profiles. In summary, compound 18b with ideal PK profiles exhibited good activity in vitro and in vivo, and might be a promising drug candidate for the treatment of diabetes mellitus.

2,2,6,6-Tetramethylpiperidine-catalyzed, ortho-selective chlorination of phenols by sulfuryl chloride

2,2,6,6-Tetramethylpiperidine (TMP)-catalyzed (1- 10%) chlorinations of phenols by SO2Cl2 in aromatic solvents are more ortho selective than with primary and less hindered secondary amine catalysts. Ortho-selective chlorination is successful even with electron deficient phenols such as 2-hydroxybenzaldehyde and 2'- hydroxyacetophenone. Notably, ortho selectivity increases with the reaction temperature. On the other hand, tetraalkylammonium chloride-catalyzed chlorinations are moderately para selective.

Affinity and activity profiling of unichiral 8-substituted 1,4-benzodioxane analogues of WB4101 reveals a potent and selective α1B- adrenoceptor antagonist

Unichiral 8-substituted analogues of 2-[(2-(2,6-dimethoxyphenoxy)ethyl) aminomethyl]-1,4-benzodioxane (WB4101) were synthesized and tested for binding affinity at cloned human α1a-, α1b-and α1d-adrenoreceptor (α1a/su

Chromenones as potent bradykinin B1 antagonists

A series of fused 6,6-bicyclic chromenones was investigated for activity against the bradykinin B1 receptor. SAR studies based on a pharmacophore model revealed compounds with high affinity for both human and rabbit B1. These compounds demonstrated favorable pharmacokinetic properties and 5-chlorochromenone 15 was efficacious in a carrageenan-induced mechanical hyperalgesia model for chronic pain.

Selective regeneration of carbonyl compounds from aldoximes and ketoximes, catalyzed by FeCl3 and SeO2

An oxidative deblocking procedure of aldoximes using FeCl3 and ketoximes using SeO2 in aprotic solvent is reported. Reaction yields are competitive as compared to previous methods. Reactions are easy to work and conditions are mild. Some important features of FeCl3 are mentioned.

Sodium perborate: A facile synthesis of 1,2-benzisoxazole 2- oxides

An efficient and convenient methodology has been developed for the conversion of 2-hydroxy phenyl ketoxime to 1,2- benzisoxazole 2-oxide with sodium perborate (SPB) in glacial acetic acid under mild reaction conditions. Interestingly when the reaction was carried out under reflux condition deoximation was observed in quantitative yield.