16216-09-4

Basic information

• Product Name: 2-(1-naphthyl)-1-phenylethanedione
• Synonyms: 2-(1-naphthyl)-1-phenylethanedione
• CAS NO: 16216-09-4
• Molecular Weight: 260.292
• Mol File: 16216-09-4.mol

Chemical Properties

• CAS DataBase Reference: 2-(1-naphthyl)-1-phenylethanedione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1-naphthyl)-1-phenylethanedione(16216-09-4)
• EPA Substance Registry System: 2-(1-naphthyl)-1-phenylethanedione(16216-09-4)

Safety Data

• Hazardous Substances Data: 16216-09-4(Hazardous Substances Data)

Usage

Physical appearance

Yellow to brown powder

Solubility

Sparingly soluble in water, soluble in organic solvents

Use as a fluorescent probe

Detects zinc ions

Potential anti-cancer properties

Being studied for its ability to inhibit cancer cell growth

Organic electronic materials

Being investigated for its potential use in organic electronic devices

Photoresist material

Being studied for its potential use in microfabrication processes

Further research needed

To determine its full range of applications and potential uses.

Upstream product

• 605-85-6 1-(1-naphthyl)-2-phenylethanone 
• 110-86-1 pyridine 
• 59387-01-8 N-(2,6-dimethylphenyl)benzenecarboximidoyl chloride 
• 4044-57-9 1-phenylethynyl-naphthalene 
• 1313850-11-1 1-(naphthalen-1-yl)-2-phenyl-2-(phenylimino)ethanone 
• 66-77-3 1-naphthaldehyde 
• 4903-36-0 N-phenyl-benzimidoyl chloride 
• 15727-65-8 1-ethynylnaphthalene 
• 100-63-0 phenylhydrazine 
• 13922-41-3 1-Naphthylboronic acid 
• 140-29-4 phenylacetonitrile 
• 90-14-2 1-Iodonaphthalene 
• 621-82-9 Cinnamic acid 
• 90-11-9 1-Bromonaphthalene 

Downstream Products

• 1051400-78-2 (S)-2-hydroxy-2-(naphthalen-1-yl)-1-phenylethanone 
• 1051400-79-3 (S)-2-hydroxy-1-(naphthalen-1-yl)-2-phenylethanone 
• 1229443-14-4 3-(1-hydroxy-2-(naphthalen-1-yl)-2-oxo-1-phenylethyl)-1-(methoxymethyl)-3,4-dihydroquinolin-2(1H)-one 
• 16303-53-0 2'--3'-phenyl-p-terphenyl 
• 23722-48-7 [1]naphthyl-phenyl-ethanedione-2-hydrazone 
• 6309-40-6 (+/-)-hydroxy-phenyl-(naphthyl-⁽¹⁾)-acetic acid 

Relevant articles and documents

Visible-Light-Induced Photocatalytic Oxidative Decarboxylation of Cinnamic Acids to 1,2-Diketones

A concerted metallophotoredox catalysis has been realized for the efficient decarboxylative functionalization of α,β-unsaturated carboxylic acids with aryl iodides in the presence of perylene bisimide dye to afford 1,2-diketones.

Synthesis of 1,2-diketones by mercury-catalyzed alkyne oxidation

The first mercury-catalyzed synthesis of 1,2-diketones by alkyne oxidation has been developed. This inexpensive method extends the potential of mercury catalysis and allows the rapid construction of various 1,2-diketones and α-carbonyl amides in good yields with high functional group tolerance.

Synthesis of unsymmetrical benzilsviapalladium-catalysed a-arylation-oxidation of 2-hydroxyacetophenones with aryl bromides

A diverse set of unsymmetrically substituted benzils were facilely synthesised by a cross-coupling reaction between 2-hydroxyacetophenones and aryl bromides in the presence of a palladium catalyst. Experimental studies suggested a reaction mechanism involving a one-pot tandem palladium-catalysed a-arylation and oxidation, where aryl bromides play a dual role as mild oxidants as well as arylating agents.

Ruthenium/dendrimer complex immobilized on silica-functionalized magnetite nanoparticles catalyzed oxidation of stilbenes to benzil derivatives at room temperature

A new ruthenium/dendrimer complex stabilized on the surface of silica-functionalized nano-magnetite was fabricated and well characterized. The nano-catalyst showed good activity in the synthesis of benzil derivatives via the oxidation of stilbenes with high turnover frequency (TOF) at room temperature. Moreover, the catalyst could also be reused up to fifteen times without any loss of its activity.

Conversion of alkynes into 1,2-diketones using HFIP as sacrificial hydrogen donor and DMSO as dihydroxylating agent

A metal-free and hypervalent iodine free conversion of internal alkynes into 1,2-diketo compounds has been described. The efficacy of the present protocol rely on the use of HFIP (1,1,1,3,3,3-Hexafluoro-2-propanol) as reducing agent of alkynes and DMSO as dihydroxylating agent of olefins to acquire the desired chemical transformations. The obtained 1,2-diketones were further transformed into useful derivatives.

Visible light-induced aerobic oxidation of diarylalkynes to α-diketones catalyzed by copper-superoxo at room temperature

We have developed the visible light induced simple copper(ii) chloride catalyzed oxidation of diarylacetylenes to α-diketones by molecular oxygen at room temperature. The in situ generated copper(ii)-superoxo complex is a light-absorbing species that oxidizes inert diarylacetylenes to α-diketones. In contrast to reported photochemical processes, the current oxidation protocol does not require any exogenous photocatalyst or radical initiator. The green chemistry metrics evaluation signifies that the E-factor for the current oxidation process is ～2.3 times better than that of reported photochemical processes. The current reaction scores 63 on the EcoScale of 0-100, indicating an adequate synthesis process. Thus, the overall oxidation process is simple, environmentally benign, and economically feasible. This journal is

1,2-dicarbonyl compound and synthesis method thereof

The invention discloses a method for synthesizing a 1,2-dicarbonyl compound (1,2-dicarbonylamide or alpha-diketone compound), wherein 1,2-dicarbonyl thioester compounds used as 1,2-dicarbonyl reagentsreact with amine compounds or boric anhydride compounds under appropriate conditions to respectively synthesize a series of 1,2-dicarbonyl compounds. According to the present invention, the 1,2-dicarbonyl compound is obtained by using the stable 1,2-dicarbonyl thioester compound as the dicarbonylation reagent through one-step construction under mild conditions, such that the disadvantage that thetraditional method uses the unstable alpha-carbonyl acyl chloride to synthesize the 1,2-dicarbonyl compound is avoided.

B2pin2-mediated copper-catalyzed oxidation of alkynes into 1,2-diketones using molecular oxygen

An intriguing aerobic oxidation of alkynes through copper catalysis is described, in which bis(pinacolato)diboron (B2pin2) played a dominant intermediary role in the formation 1,2-diketones. This novel protocol, which can be performed at room temperature, is versatile for various substituted alkynes, including diarylalkynes and arylalkylalkynes. The mechanism of this reaction was preliminarily investigated by control experiments.

Electrochemical synthesis of 1,2-diketones from alkynes under transition-metal-catalyst-free conditions

We report an electrochemical protocol for the direct oxidation of internal alkynes in air to provide 1,2-diketones. A variety of functional groups and heterocycle-containing substrates can be tolerated well under mild conditions.

Two-Step One-Pot Synthesis of Unsymmetrical (Hetero)Aryl 1,2-Diketones by Addition-Oxygenation of Potassium Aryltrifluoroborates to (Hetero)Arylacetonitriles

An efficient one-pot two-step procedure for the synthesis of unsymmetrical (hetero)aryl 1,2-diketones has been developed. The reaction proceeds through a palladium-catalyzed nucleophilic addition of potassium aryltrifluoroborates to aliphatic nitriles followed by a copper-catalyzed aerobic benzylic C–H oxygenation using molecular oxygen as a green oxidant. This represents the first example of the direct synthesis of unsymmetrical diaryl 1,2-diketones from arylacetonitriles. This method utilizes inexpensive, stable, nontoxic, and readily available starting materials, is highly effective in the presence of both electron-rich and electron-poor nitriles and aryltrifluoroborates, and tolerates a wide variety of functional groups. The synthetic utility of this transformation was shown by increasing the scale of the reaction and by carrying out the one-pot protocol for the preparation of quinoxaline and benzimidazole derivatives. A plausible reaction mechanism has also been proposed.