86293-52-9

Basic information

• Product Name: 1-(4-CHLORO-PHENYL)-3-(3-HYDROXY-PHENYL)-PROPENONE
• Synonyms: (E)-1-(4-CHLOROPHENYL)-3-(3-HYDROXYPHENYL)-2-PROPEN-1-ONE;1-(4-CHLOROPHENYL)-3-(3-HYDROXYPHENYL)-2-PROPEN-1-ONE;1-(4-CHLORO-PHENYL)-3-(3-HYDROXY-PHENYL)-PROPENONE
• CAS NO: 86293-52-9
• Molecular Formula: C₁₅H₁₁ClO₂
• Molecular Weight: 258.7
• Mol File: 86293-52-9.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 400°C
• Flash Point: 227.9°C
• Appearance: /
• Density: 1.292g/cm³
• Vapor Pressure: 7.8E-09mmHg at 25°C
• Refractive Index: 1.659
• PKA: 9.47±0.10(Predicted)
• CAS DataBase Reference: 1-(4-CHLORO-PHENYL)-3-(3-HYDROXY-PHENYL)-PROPENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-CHLORO-PHENYL)-3-(3-HYDROXY-PHENYL)-PROPENONE(86293-52-9)
• EPA Substance Registry System: 1-(4-CHLORO-PHENYL)-3-(3-HYDROXY-PHENYL)-PROPENONE(86293-52-9)

Safety Data

• Hazardous Substances Data: 86293-52-9(Hazardous Substances Data)

Usage

General Description

1-(4-CHLORO-PHENYL)-3-(3-HYDROXY-PHENYL)-PROPENONE is a chemical compound that consists of a 1-(4-chloro-phenyl) group attached to a 3-(3-hydroxy-phenyl) group through a propenone linkage. It is a yellow crystalline solid that is commonly used in organic synthesis as a starting material for various pharmaceutical and agrochemical products. 1-(4-CHLORO-PHENYL)-3-(3-HYDROXY-PHENYL)-PROPENONE possesses both aromatic and ketonic functional groups, making it useful for a wide range of chemical reactions. Its structural properties make it an important intermediate in the production of various drugs, organic compounds, and materials. However, it is important to handle this chemical with caution due to its potential hazardous properties.

InChI:InChI=1/C15H11ClO2/c16-13-7-5-12(6-8-13)15(18)9-4-11-2-1-3-14(17)10-11/h1-10,17H/b9-4+

Upstream product

• 99-91-2 para-chloroacetophenone 
• 100-83-4 meta-hydroxybenzaldehyde 

Downstream Products

• 1375113-29-3 3-(2-(4-chlorophenyl)-6-(furan-2-yl)pyridin-4-yl)phenol 
• 1375113-32-8 3-(6-(4-chlorophenyl)-2,4'-bipyridin-4-yl)phenol 
• 1375113-31-7 3-(6-(4-chlorophenyl)-2,3'-bipyridin-4-yl)phenol 
• 1375113-27-1 3-(2-(4-chlorophenyl)-6-(thiophen-2-yl)pyridin-4-yl)phenol 
• 1375113-30-6 3-(6-(4-chlorophenyl)-[2,2'-bipyridin]-4-yl)phenol 
• 1375113-28-2 3-(2-(4-chlorophenyl)-6-(thiophen-3-yl)pyridin-4-yl)phenol 

Relevant articles and documents

Hydroxyl- and Halogen-containing Chalcones for the Inhibition of LPS-stimulated ROS Production in RAW 264.7 Macrophages: Design, Synthesis and Structure–Activity Relationship Study

Oxidative stress due to overproduction of reactive oxygen species (ROS) plays a major role in inflammation, cancer, and neurodegenerative disorders. In this study, 60 chalcone derivatives with fluorine (F), trifluoromethyl (CF3), trifluoromethoxy (OCF3), chlorine (Cl), and bromine (Br) in ring A and with or without hydroxy (OH) in ring B were designed, synthesized, and screened for inhibitory activity against lipopolysaccharide (LPS)-stimulated ROS production in RAW 264.7 macrophages. Structure–activity relationship study revealed the importance of a hydroxyl moiety in ring B for enhancing inhibitory activity of ROS production. Furthermore, a hydroxyl group at the ortho-position is more essential for inhibition of ROS production followed by meta- and para-positions. Among all, compound 27 that contains para-chlorine moiety in ring A and ortho-hydroxy in ring B displayed the strongest inhibitory activity (IC50 = 3.42 μM) against LPS-stimulated ROS production in RAW264.7 macrophages.

β-Cyclodextrin/IBX in water: Highly facile biomimetic one pot deprotection of THP/MOM/Ac/Ts ethers and concomitant oxidative cleavage of chalcone epoxides and oxidative dehydrogenation of alcohols

A mild and efficient one-pot deprotection of THP/MOM/Ac/Ts ethers, and concomitant oxidative cleavage of epoxides and oxidative dehydrogenation of alcohols to form β-hydroxy 1,2-diketones, 1,2,3-triketones and conjugated aromatic carbonyl systems (chalcones) using β-cyclodextrin/IBX in water has been developed. o-Iodoxybenzoic acid, a readily available hypervalent iodine(v) reagent, was found to be highly effective with β-cyclodextrin in carrying out the deprotection and subsequent transformations under an eco-friendly environment. The reaction gave moderate to excellent yields ranging from 50-99% at 60°C in 40 min to 6 h.

β-Cyclodextrin in water: Highly facile biomimetic one pot deprotection of phenolic THP/MOM/Ac/Ts ethers and concomitant regioselective cyclization of chalcone epoxides and 2′-aminochalcones

A mild and efficient one-pot deprotection of THP/MOM/Ac/Ts ethers and the concomitant cyclization of chalcone epoxides to 2-hydroxyindanones or 2′-aminochalcones to aza-flavanones using β-cyclodextrin in water has been developed. β-CD was found to be highly effective at carrying out the deprotection and sequential transformations in an eco-friendly environment affording moderate to excellent yields (59-99%) at 60 °C in 8-22 min. Water, an eco-friendly reaction medium, has been utilized for the first time in this reaction. The merits of the presented protocol include the high yields and catalyst reusability and the protocol precludes the use of metals and organic solvents. The present method is much milder but more advanced than those reported earlier.