3226-34-4

Basic information

• Product Name: 1-(3-CHLORO-2-HYDROXYPHENYL)ETHAN-1-ONE
• Synonyms: ASISCHEM D38763;1-(3-CHLORO-2-HYDROXYPHENYL)ETHAN-1-ONE;2-HYDROXY-3-CHLOROACETOPHENONE;3'-Chloro-2'-hydroxyacetophenone;1-(3-Chloro-2-hydroxyphenyl)ethanone;1-(3-Chloro-2-hydroxyphenyl)ethan-1-one, 2-Acetyl-6-chlorophenol
• CAS NO: 3226-34-4
• Molecular Formula: C₈H₇ClO₂
• Molecular Weight: 170.59
• Product Categories: Aromatics
• Mol File: 3226-34-4.mol
• Article Data: 13

Chemical Properties

• Melting Point: 80 °C
• Boiling Point: 247.1°Cat760mmHg
• Flash Point: 103.2°C
• Appearance: /
• Density: 1.298g/cm³
• Vapor Pressure: 0.0167mmHg at 25°C
• Refractive Index: 1.569
• Storage Temp.: -20°C Freezer
• Solubility: Dichloromethane, Ethyl Acetate, Methanol
• PKA: 8.69±0.10(Predicted)
• CAS DataBase Reference: 1-(3-CHLORO-2-HYDROXYPHENYL)ETHAN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-CHLORO-2-HYDROXYPHENYL)ETHAN-1-ONE(3226-34-4)
• EPA Substance Registry System: 1-(3-CHLORO-2-HYDROXYPHENYL)ETHAN-1-ONE(3226-34-4)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 3226-34-4(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

Uses

2’-Hydroxy-3-chloroacetophenone (cas# 3226-34-4) is a compound useful in organic synthesis.

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

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

Downstream Products

• 778639-42-2 2-methyl-5-propyl-2H-pyrazole-3-carboxylic acid 2-acetyl-6-chloro-phenyl ester 
• 84314-43-2 1-(3-Chloro-2-hydroxy-phenyl)-3-(4-hydroxy-phenyl)-2-[1-(4-hydroxy-phenyl)-meth-(E)-ylidene]-propane-1,3-dione 
• 84314-44-3 1-(3-Chloro-2-hydroxy-phenyl)-3-(4-hydroxy-phenyl)-2-[1-(2-hydroxy-phenyl)-meth-(E)-ylidene]-propane-1,3-dione 
• 84314-52-3 8-Chloro-3-(4-hydroxy-benzoyl)-2-(4-hydroxy-phenyl)-chromen-4-one 
• 84314-53-4 8-Chloro-3-(4-hydroxy-benzoyl)-2-(2-hydroxy-phenyl)-chromen-4-one 
• 84314-45-4 1-(3-Chloro-2-hydroxy-phenyl)-3-(4-hydroxy-phenyl)-2-[1-(4-nitro-phenyl)-meth-(E)-ylidene]-propane-1,3-dione 
• 84340-50-1 8-Chloro-3-(4-hydroxy-benzoyl)-2-(4-nitro-phenyl)-chromen-4-one 
• 3260-93-3 3-chloro-2-methoxybenzoic acid 
• 1353024-73-3 C₁₆H₁₃ClO₃ 
• 1354928-55-4 C₁₇H₁₁ClO₄ 
• 1354928-60-1 C₁₇H₁₁ClO₄ 
• 56207-40-0 2-benzyloxy-3-chlorophenol 
• 1416443-70-3 (R)-3-(2-benzyloxy-3-chlorophenoxy)-1,2-propanediol 
• 1416443-68-9 C₁₉H₂₂ClNO₅*ClH 

Relevant articles and documents

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.

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

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.