60721-33-7

Basic information

• Product Name: 1-(4-CHLORO-PHENYL)-4-PHENYL-BUTANE-1,4-DIONE
• Synonyms: 1-(4-CHLORO-PHENYL)-4-PHENYL-BUTANE-1,4-DIONE
• CAS NO: 60721-33-7
• Molecular Formula: C₁₆H₁₃ClO₂
• Molecular Weight: 272.72622
• Mol File: 60721-33-7.mol

Chemical Properties

• Melting Point: 110 °C
• Boiling Point: 439.2°C at 760 mmHg
• Flash Point: 185.2°C
• Appearance: /
• Density: 1.21g/cm³
• Vapor Pressure: 6.48E-08mmHg at 25°C
• Refractive Index: 1.583
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1-(4-CHLORO-PHENYL)-4-PHENYL-BUTANE-1,4-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-CHLORO-PHENYL)-4-PHENYL-BUTANE-1,4-DIONE(60721-33-7)
• EPA Substance Registry System: 1-(4-CHLORO-PHENYL)-4-PHENYL-BUTANE-1,4-DIONE(60721-33-7)

Safety Data

• Hazardous Substances Data: 60721-33-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Chalcone is used as an intermediate for the development of new pharmaceuticals due to its potential biological activities, including antioxidant, anti-inflammatory, anti-cancer, and anti-microbial properties. Its molecular structure containing a ketone group and a phenyl ring allows for the creation of versatile compounds with various therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, chalcone is utilized as an intermediate for the synthesis of various agrochemicals, taking advantage of its biological activities to develop compounds that can be used in pest control and crop protection.
Used in Dye Industry:
Chalcone is used as a dye intermediate, contributing to the production of a range of dyes for different applications, including textiles, plastics, and other industrial processes.
Used in Rubber and Plastics Industry:
Chalcone is employed in the production of additives for the rubber and plastics industry, enhancing the properties of these materials and improving their performance in various applications.
Used in Functional Materials:
Due to its versatile molecular structure, chalcone is also used in the development of functional materials with specific properties, such as conductivity, magnetism, or optical characteristics, for use in various high-tech applications.

InChI:InChI=1/C16H13ClO2/c17-14-8-6-13(7-9-14)16(19)11-10-15(18)12-4-2-1-3-5-12/h1-9H,10-11H2

Upstream product

• 860764-08-5 2-(4-chloro-benzoyl)-4-oxo-4-phenyl-butyric acid ethyl ester 
• 18338-90-4 5-(4-chlorophenyl)-2(3H)-furanone 
• 71-43-2 benzene 
• 583-06-2 3-benzoylacrylic acid 
• 104-88-1 4-chlorobenzaldehyde 
• 29113-50-6 2-benzoyl-4-(4-chloro-phenyl)-4-oxo-butyric acid ethyl ester 
• 532-27-4 1-chloroacetophenone 
• 201230-82-2 carbon monoxide 
• 768-03-6 Phenyl vinyl ketone 
• 58518-76-6 ((1-(4-chlorophenyl)vinyl)oxy)trimethylsilane 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 107487-79-6 trans-1-(4-Chlorophenyl)-4-phenylbut-2-ene-1,4-dione 
• 70-11-1 α-bromoacetophenone 
• 536-38-9 4-chlorobenzoylmethyl bromide 

Downstream Products

• 1223429-83-1 (3-benzoylnaphthalen-2-yl)(4-chlorophenyl)methanone 

Relevant articles and documents

Asymmetric hydrogenation of 1,4-diketones: facile synthesis of enantiopure 1,4-diarylbutane-1,4-diols

Owing to the biological significance and great synthetic value of 1,4-diarylbutane-1,4-diols and their derivatives, increasingly considerable attention has been paid to developing effective synthetic methods for chiral 1,4-diarylbutane-1,4-diols. We herei

A method of synthesizing chiral alkene propyl alcohol

The invention discloses a method for synthesizing chiral alkene propyl alcohol method, which belongs to the technical field of organic chemistry. The method adopts the [...] derived binaphthol potassium salt as a chiral [...] catalyst, catalytic [...] pro

Proton-Coupled Electron Transfer: Transition-Metal-Free Selective Reduction of Chalcones and Alkynes Using Xanthate/Formic Acid

Highly chemoselective reduction of α,β-unsaturated ketones to saturated ketones and stereoselective reduction of alkynes to (E)-alkenes has been developed under a transition-metal-free condition using a xanthate/formic acid mixture through proton-coupled electron transfer (PCET). Mechanistic experiments and DFT calculations support the possibility of a concerted proton electron-transfer (CPET) pathway. This Birch-type reduction demonstrates that a small nucleophilic organic molecule can be used as a single electron-transfer (SET) reducing agent with a proper proton source.

Kinetic Resolution of Allylic Alcohol with Chiral BINOL-Based Alkoxides: A Combination of Experimental and Theoretical Studies

The development and characterization of enantioselective catalytic kinetic resolution of allylic alcohols through asymmetric isomerization with chiral BINOL derivatives-based alkoxides as bifunctional Br?nsted base catalysts were described in the study. A number of chiral BINOL derivatives-based alkoxides were synthesized, and their structure-enantioselectivity correlation study in asymmetric isomerization identified a promising chiral Br?nsted base catalyst, which afforded various chiral secondary allylic alcohols (ee up to 99%, S factor up to >200). In the mechanistic study, alkoxide species were identified as active species and the phenol group of BINOL largely affected the high reactivity and enantioselectivity via hydrogen bonding between the chiral Br?nsted base catalyst and substrates. The strategy is the first successful synthesis strategy of various chiral secondary allylic alcohols through enantioselective transition-metal-free base-catalyzed isomerization. The applicability of the strategy had been demonstrated by the synthesis of the bioactive natural product (+)-veraguensin.

Cross-coupling of dissimilar ketone enolates via enolonium species to afford non-symmetrical 1,4-diketones

Due to their closely matched reactivity, the coupling of two dissimilar ketone enolates to form a 1,4-diketone remains a challenge in organic synthesis. We herein report that umpolung of a ketone trimethylsilyl enol ether (1 equiv) to form a discrete enol

Detrifluoroacetylation Reaction of Trifluoromethyl-β-diketones: Facile Method for the Synthesis of Succinimide Derivatives and 1,4-Diketones

Currently, a great deal of research efforts are focused on C–C bond activation for development of novel synthetic methodology. In this paper, a detrifluoroacetylation of trifluoromethyl-β-diketones is described, which allows for the synthesis of succinimides and 1,4-diketones through cascade Michael addition/retro-Claisen reaction and nucleophilic substitution/retro-Claisen reaction. The readily available trifluoromethyl-β-diketones, wide substrate scope, and mild conditions make this method very practical.

Carbonylative 1,4-addition of potassium aryltrifluoroborates to vinyl ketones

Potassium aryltrifluoroborates have proven to be useful reagents for the carbonylative aroylation of vinyl ketones; this study broadens the scope of potassium aryltrifluoroborates in homogeneous catalysis and shows that the solvent can act as the proton s

Zinc-mediated chain extension reaction of 1,3-diketones to 1,4-diketones and diastereoselective synthesis of trans-1,2-disubstituted cyclopropanols

A variety of 1,3-diketones can be efficiently converted into the corresponding 1,4-diketones and trans-1,2-disubstituted cyclopropanols by using organozinc species in one-pot reactions. It was found that 2.3 equiv of CF 3CO2ZnCH2I was effective to give the corresponding chain-extended products in 44-85% yields, while a mixture of organozinc species formed from 4.0 equiv of Et2Zn, 2.0 equiv of CF3CO2H, and 4.0 equiv of CH2I2 resulted in the formation of trans-1,2-disubstituted cyclopropanols with quite good yields and diastereoselectivity.

Cross-coupling reaction of α-chloroketones and organotin enolates catalyzed by zinc halides for synthesis of γ-diketones

The reaction of tin enolates 1 with α-chloro- or bromoketones 2 gave γ-diketones (1,4-diketones) 3 catalyzed by zinc halides. In contrast to the exclusive formation of 1,4-diketones 3 under catalytic conditions, uncatalyzed reaction of 1 with 2 gave aldol-type products 4 through carbonyl attack. NMR study indicates that the catalyzed reaction includes precondensation between tin enolates and α-haloketones providing an aldol-type species and their rearrangement of the oxoalkyl group with leaving halogen to produce 1,4-diketones. The catalyst, zinc halides, plays an important role in each step. The carbonyl attack for precondensation is accelerated by the catalyst as Lewis acid and the intermediate zincate promotes the rearrangement by releasing oxygen and bonding with halogen. Various types of tin enolates and α-chloro and bromoketones were applied to the zinc-catalyzed cross-coupling. On the other hand, the allylic halides, which have no carbonyl moiety, were inert to the zinc-catalyzed coupling with tin enolates. The copper halides showed high catalytic activity for the coupling between tin enolates 1 and organic halides 7 to give γ,δ-unsaturated ketones 8 and/or 9. The reaction with even chlorides proceeded effectively by the catalytic system.

Carbon-Carbon Bond Formation in Reactions of PhIO*HBF4/Silyl Enol Ether Adduct with Alkenes or Silyl Enol Ethers

A new method for generation of reactive α-ketomethyl aryliodonium intermediates from silyl enol ethers and PhIO*HBF4 has been developed.Reactions of PhIO*HBF4/silyl enol ether adduct with alkenes (1-hexene, cyclohexene, α-methylstyrene, allyltrimethylsilane, 2,3-dimethyl-2-butene) yielded products of allylic alkylation or (in case of 2,3-dimethyl-2-butene) a substituted dihydrofuran.Reactions of adducts from PhIO/HBF4 and silyl enol ethers of acetophone, p-chloroacetophenone, p-methylacetophenone, and p-nitroacetophenone with various silyl enol ethers led to unsymmetrical 1,4-butanediones as major products.