3442-15-7

Basic information

• Product Name: (Z)-4-hydroxy-1,4-diphenyl-but-3-en-2-one
• Synonyms: (Z)-4-hydroxy-1,4-diphenyl-but-3-en-2-one
• CAS NO: 3442-15-7
• Molecular Formula: C₁₆H₁₄O₂
• Molecular Weight: 0
• Mol File: 3442-15-7.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 424.8°Cat760mmHg
• Flash Point: 181.3°C
• Appearance: /
• Density: 1.158g/cm³
• Vapor Pressure: 5.64E-08mmHg at 25°C
• Refractive Index: 1.611
• CAS DataBase Reference: (Z)-4-hydroxy-1,4-diphenyl-but-3-en-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-4-hydroxy-1,4-diphenyl-but-3-en-2-one(3442-15-7)
• EPA Substance Registry System: (Z)-4-hydroxy-1,4-diphenyl-but-3-en-2-one(3442-15-7)

Safety Data

• Hazardous Substances Data: 3442-15-7(Hazardous Substances Data)

Usage

General Description

(Z)-4-hydroxy-1,4-diphenyl-but-3-en-2-one, also known as chalcone, is a yellow crystalline compound with a variety of potential chemical and medicinal applications. It is a member of the chalcone family of compounds, which are known for their antibacterial, antifungal, antioxidant, and anti-inflammatory properties. Chalcone has been studied for its potential use in treating a range of conditions, including cancer, diabetes, and neurodegenerative diseases. It is also used in the synthesis of various pharmaceutical drugs and as a chemical intermediate in the production of other compounds. Additionally, chalcone has been studied for its potential use as a natural dye and as a fluorescent probe in biological imaging.

InChI:InChI=1/C16H14O2/c17-15(11-13-7-3-1-4-8-13)12-16(18)14-9-5-2-6-10-14/h1-10,12,18H,11H2/b16-12-

Upstream product

• 101-97-3 Ethyl 2-phenylethanoate 
• 98-86-2 acetophenone 
• 27735-65-5 2-(dimethyl-λ4-sulfanylidene)-1,4-diphenyl-butane-1,3-dione 
• 122-78-1 phenylacetaldehyde 
• 3282-32-4 2-diazo-acetophenone 
• 101-41-7 benzeneacetic acid methyl ester 
• 140-29-4 phenylacetonitrile 
• 70-11-1 α-bromoacetophenone 
• 55490-02-3 2-bromo-4-nitro-1,3-diphenyl-butan-1-one 
• 89036-99-7 Acetic acid 2-methoxy-1-phenyl-2-phenylsulfanyl-ethyl ester 
• 89036-90-8 2-Methoxy-1-phenyl-2-phenylsulfanyl-ethanol 
• 121862-21-3 3-Methoxy-1,4-diphenyl-4-phenylsulfanyl-butan-1-one 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 93-89-0 benzoic acid ethyl ester 

Downstream Products

• 955-10-2 3-phenylcumarin 
• 499241-22-4 3-amino-1,4-diphenylbut-2-en-1-one 
• 499240-97-0 3-[(4-methoxybenzyl)amino]-1,4-diphenylbut-2-en-1-one 
• 81385-87-7 2-methyl-1,4-diphenyl-1,3-butanedione 
• 499241-14-4 8-benzoyl-6,7-dibenzyl-2-chloro-3-fluoro-5,6-dihydro-1,6-naphthyridin-5-one 
• 499241-10-0 8-benzoyl-7-benzyl-6-(4-methoxybenzyl)-5,6-dihydro-1,6-naphthyridin-5-one 

Relevant articles and documents

Variations in the blaise reaction: Conceptually new synthesis of 3-amino enones and 1,3-diketones

Organic compounds with 3-amino enone or 1,3-diketone functional groups are extremely important, as they can be converted into a plethora of heterocyclic or carbocyclic compounds, or can be used as ligands in metal complexes. We have achieved a new, easy, straightforward and convenient synthesis of 3-amino enones and 1,3-diketones starting from aryl/heteroaryl/alkyl nitriles and 1-aryl/alkyl 2-bromoethanones. The reaction is a variation of the classical Blaise reaction, and it works with zinc and trimethylsilyl chloride as an activator. By running the hydrolysis of the reaction intermediate with HCl (3 N aq.) at 0-30 °C or at 100 °C, it is possible to form either 3-amino enones or 1,3-diketones, respectively. The newly developed method was used for the synthesis of avobenzone, an ingredient of sun-screen lotions. Furthermore, an easy synthesis of (Z)-3-amino-1-[4-(tertbutyl) phenyl]-3-(4-methoxyphenyl)prop-2-en-1-one, with UV/Vis absorption characteristics similar to those of avobenzone, was also achieved.

Et2Zn-mediated rearrangement of bromohydrins

(Chemical Equation Presented) A simple and highly efficient method for the rearrangement of bromohydrins mediated by Et2Zn to synthesize carbonyl compounds was described. Various β-bromo alcohols were treated with 0.6 equiv of Et2Zn to form a zinc complex in CH 2Cl2 at room temperature for 2 h, followed by 1,2-migration to give the corresponding carbonyl compounds. This remarkable and clean rearrangement is general for acyclic and cyclic bromohydrins, and a variety of ring-expansive and -contractive carbonyl compounds were obtained in good to excellent yields according to the feature of the starting bromohydrins. The functional group tolerance of organozinc reagents in this reaction will be useful in organic synthesis. The scope and limitations of this rearrangement process were also investigated.

Zinc-mediated C-C bond sigmatropic rearrangement: A new and efficient methodology for the synthesis of β-diketones

(Chemical Equation Presented) A new and efficient methodology has been developed for the synthesis of β-diketones from aromatic α-bromo ketones in the presence of Furukawa reagent under mild conditions. The present transformation is proposed to proceed via a Reformatsky-type reaction of α-bromo ketones, followed by C-C bond sigmatropic rearrangement of the aldolate intermediate to give β-diketones in moderate to good isolated yields, while aliphatic α-bromomethyl ketones resulted in the formation of 2,4-disubstituted furans or cis-1,2-disubstituted cyclopropanols in moderate yields. The scope of this process was investigated, and a tentative mechanism was proposed.