959-27-3

Basic information

• Product Name: (Z)-1,4-Diphenyl-2-butene-1,4-dione
• Synonyms: (Z)-1,2-Dibenzoylethene;(Z)-1,4-Diphenyl-2-butene-1,4-dione
• CAS NO: 959-27-3
• Molecular Formula: C₁₆H₁₂O₂
• Molecular Weight: 0
• Mol File: 959-27-3.mol
• Article Data: 29

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (Z)-1,4-Diphenyl-2-butene-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-1,4-Diphenyl-2-butene-1,4-dione(959-27-3)
• EPA Substance Registry System: (Z)-1,4-Diphenyl-2-butene-1,4-dione(959-27-3)

Safety Data

• Hazardous Substances Data: 959-27-3(Hazardous Substances Data)

Usage

Description

(Z)-1,4-Diphenyl-2-butene-1,4-dione, commonly known as chalcone, is a yellow crystalline solid that belongs to the class of organic compounds known as chalcones. It is typically produced by the Claisen-Schmidt reaction, where an aldehyde reacts with a ketone in the presence of a strong base. Chalcone possesses fluorescent properties and is valued for its potential in medicinal chemistry, particularly as a starting material for the synthesis of biologically active compounds such as flavonoids, which exhibit antioxidant, anti-inflammatory, and anticancer properties.

Uses

Used in Medicinal Chemistry:
Chalcone is used as a starting material for the synthesis of various biologically active compounds, such as flavonoids, which are known for their antioxidant, anti-inflammatory, and anticancer properties. This application is due to chalcone's ability to serve as a versatile building block in the development of pharmaceuticals.
Used in the Textile Industry:
Chalcone is used as a dye in the textile industry, taking advantage of its fluorescent properties to create vibrant colors in fabrics.
Used in Optoelectronic Devices:
Chalcone has potential applications in the development of organic light-emitting diodes (OLEDs) and other optoelectronic devices, leveraging its fluorescent characteristics to enhance the performance of these technologies.

Upstream product

• 955-83-9 2,5-diphenylfuran 
• 67-66-3 chloroform 
• 546-67-8 lead(IV) tetraacetate 
• 23637-57-2 (Z)-1,4-diphenylbut-2-ene-1,4-diol 
• 532-27-4 1-chloroacetophenone 
• 959-28-4 1,4-diphenylbut-2-ene-1,4-dione 
• 838-40-4 2,5-diphenyl-1H-pyrrole 
• 1445-78-9 2,5-Diphenyl-thiophene 
• 92670-73-0 2-<1-(3,5-diphenylpyrazolyl)>-1,4-diphenylbutane-1,4-dione 
• 1074-12-0 phenylglyoxal hydrate 
• 20913-05-7 (Benzoylmethylene)triphenylphosphorane 
• 5369-55-1 2,4-diphenylfuran 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 

Downstream Products

• 160620-54-2 3,4-dibenzoyl-4,5-dihydro-1H-pyrazole 
• 975-70-2 (6-benzoyl-3,4-dimethylcyclohex-3-enyl)(phenyl)methanone 
• 4440-98-6 trans-2,3-Epoxy-1,4-diphenyl-1,4-butanedione 
• 107519-54-0 3-chloro-2,5-diphenyl-furan 
• 107487-41-2 4-hydroxy-1,4-diphenylbutan-1-one 
• 107538-22-7 meso-1.4-diphenyl-butene-(2t)-diol-(1.4) 
• 54795-41-4 1ξ-Phenyl-2ξ.3r.4t-tribenzoyl-cyclopentanol-(1ξ) 
• 959-28-4 1,4-diphenylbut-2-ene-1,4-dione 
• 495-71-6 phenacylacetophenone 
• 54795-41-4 1-phenyl-2ξ.3r.4c-tribenzoyl-cyclopentanol-(1) 
• 74007-33-3 2endo.3endo-dibenzoyl-norbornene-⁽⁵⁾ 
• 21939-15-1 C,C'-diphenyl-C,C'-(2-methyl-3c-phenyl-isoxazolidine-4r,5c-diyl)-bis-methanone 
• 54169-83-4 C,C'-diphenyl-C,C'-(4,5α-epoxy-3,6-dimethoxy-17-methyl-6α,14α-etheno-morphinane-7α,8α-diyl)-bis-methanone 
• 54191-62-7 C,C'-diphenyl-C,C'-(4,5α-epoxy-3,6-dimethoxy-17-methyl-6α,14α-etheno-morphinane-7β,8α-diyl)-bis-methanone 

Relevant articles and documents

An Efficient Regeneration of Singlet Oxygen from 2,5-Diphenylfuran Endoperoxide Produced by a Dye-Sensitized Oxygenation

The maximum quantum yield of 4.5 was evaluated from the kinetic analysis for the Methylene Blue-sensitized oxygenation of 2,5-diphenylfuran, and the contribution of a chain process to produce the furan endoperoxide was suggested.After the photoreaction, t

Oxidation of sesamol dimer by active species produced in the interaction of peroxide and hemoglobin

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Aerobic Oxidative Dehydrogenation of Ketones to 1,4-Enediones

An efficient and unprecedented strategy for the synthesis of 1,4-enediones from saturated ketones has been developed via palladium-catalyzed oxidative dehydrogenation. The protocol employs molecular oxygen as the sole oxidant and represents an atom- and step-economic process. The approach showed broad substrate scope, good functional group tolerance, and complete E-stereoselectivity. The reaction mechanism has been investigated through deuterium-labeling experiments and intermediate experiments.

Visible-light-mediated oxidative dimerization of arylalkynes in the open air: Stereoselective synthesis of (Z)-1,4-enediones

An organic photoredox catalytic one-pot protocol is developed for the highly stereoselective synthesis of (Z)-1,4-enediones. The reaction starts directly from alkyne precursors, using 4-(4-cyanophenyl)-2,6-diphenylpyrylium tetrafluoroborate (CN-TPT) as an efficient photosensitizer and dioxygen in the air as a green oxidant. A Csp-Csp oxidative coupling/[4 + 2] cyclization (with dioxygen)/fragmentive isomerization cascade mechanism was proposed. The predominant formation of (Z)-1,4-enediones is attributed to the efficient visible-light illumination from blue LEDs, along with possible energy transfer from the photosensitizer CN-TPT to the E-isomers.