1150-59-0

Basic information

• Product Name: 4-hydroxy-3-phenylnaphthalene-1,2-dione
• Synonyms: 1,2-naphthalenedione, 4-hydroxy-3-phenyl-
• CAS NO: 1150-59-0
• Molecular Formula: C₁₆H₁₀O₃
• Molecular Weight: 250.2488
• Mol File: 1150-59-0.mol

Chemical Properties

• Boiling Point: 445.3°C at 760 mmHg
• Flash Point: 237.2°C
• Density: 1.392g/cm³
• Vapor Pressure: 1.04E-08mmHg at 25°C
• Refractive Index: 1.693
• CAS DataBase Reference: 4-hydroxy-3-phenylnaphthalene-1,2-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 4-hydroxy-3-phenylnaphthalene-1,2-dione(1150-59-0)
• EPA Substance Registry System: 4-hydroxy-3-phenylnaphthalene-1,2-dione(1150-59-0)

Safety Data

• Hazardous Substances Data: 1150-59-0(Hazardous Substances Data)

Upstream product

• 938-24-9 indantrione 
• 908094-04-2 phenyldiazomethane 
• 2684-02-8 benzenediazonium 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 2348-77-8 2-phenyl[1,4]naphthoquinone 
• 13148-15-7 2-phenylnaphthalene-1,3-diol 
• 108732-57-6 4-anilino-3-phenyl-1,2-naphthoquinone 
• 71202-25-0 (2,4-Dihydroxy-3-phenyl-1-naphthyl)phenylmethanon 
• 15451-41-9 2-hydroxy-3-benzyl-1,4-naphthoquinone 
• 1681-79-4 3-(phenylmethylene)-1H-2-benzopyran-1,4(3H)-dione 
• 524-42-5 1,2-naphthoquinone 
• 103-82-2 phenylacetic acid 
• 101-97-3 Ethyl 2-phenylethanoate 
• 117560-06-2 3-phenyliodonio-1,2,4-trioxo-1,2,3,4-tetrahydronaphthalenide 

Downstream Products

• 53271-83-3 2-methoxy-3-phenyl-[1,4]naphthoquinone 
• 106-34-3 quinhydrone 
• 65-85-0 benzoic acid 
• 528-46-1 phthalonic acid 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 18398-22-6 3-benzoylisobenzofuran-1(3H)-one 
• 102183-62-0 2-(3-phenyl-quinoxalin-2-yl)-benzaldehyde 
• 103985-77-9 N-[2-(3-phenyl-quinoxalin-2-yl)-benzylidene]-o-phenylenediamine 

Relevant articles and documents

1,4-Naphthoquinones potently inhibiting P2X7 receptor activity

P2X7 receptor (P2X7R) is an ATP-gated ion-channel with potential therapeutic applications. In this study, we prepared and searched a series of 1,4-naphthoquinones derivatives to evaluate their antagonistic effect on both human and murine P2X7 receptors. W

Suzuki-Miyaura coupling between 3-iodolawsone and arylboronic acids. Synthesis of lapachol analogues with antineoplastic and antileishmanial activities

A series of 2-hydroxy-3-arylnaphthalene-1,4-diones (3-aryllawsones) were synthesized by Suzuki-Miyaura cross coupling reaction of 3-iodolawsone with arylboronic acids/esters. The hydroxylated resulting products were transformed into their corresponding N,N-diethyl carbamates. The antineoplastic and antileishmanial activities of the compounds were evaluated and compared with lapachol and its carbamate, providing promising results.

Pd(II)-Catalyzed Synthesis of Alkylidene Phthalides via a Decarbonylative Annulation Reaction

An unprecedented Pd(II)-catalyzed decarbonylative C-H/C-C activation and annulation reaction, which proceeds via intramolecular cyclization, is reported. This reaction of hydroxynaphthoquinones with disubstituted alkynes provides good yields of substituted alkylidene phthalides, which are the key intermediates for the synthesis of bioactive natural products.

Pd/C-catalyzed dehydrogenation of 2-cinnamoylbenzoic acids to 3-benzylidene-3H-isochroman-1,4-diones

Pd/C, a widely accepted hydrogenation catalyst, is found to catalytically dehydrogenate 2-cinnamoylbenzoic acids to 3-benzylidene-3-H-isochroman-1,4-diones with H2 as the only byproduct. This synthetic reaction proceeds without oxidants and hydrogen acceptors, thereby representing an atom- and step-efficient approach to a wide range of functionalized 3-benzylidene-3H-isochroman-1,4-diones.

Transition metal mediated selective C vs N arylation of 2-aminonaphthoquinone and its application toward the synthesis of benzocarbazoledione

Selective C vs N-arylation of 2-aminonaphthoquinone was achieved using different transition metal salts and arylboronic acids. Mn(OAc)3·2H2O provided C-arylated product whereas NiCl2·6H2O and Cu(OAc)2

Synthesis, characterization and biological activities of 3-aryl-1,4-naphthoquinones-green palladium-catalysed Suzuki cross coupling

Quinones are important scaffolds that are present in a variety of natural products or synthetic bioactive molecules. Arylation is an important strategy for accomplishing structural modifications, leading to new potential candidates for use as drugs. In the present work, palladium-catalysed, ligandless and phosphine-free Suzuki coupling reactions between 2-hydroxy-3-iodo-1,4-naphthoquinone and boronic acids were employed to prepare several 2-hydroxy-3-aryl-1,4-naphthoquinones in aqueous conditions using microwave irradiation or conventional heating. Because of the biological activities of quinones, which are related to their ability to accept electrons to form semiquinones and hydroquinones, the electrochemical behaviour of the synthesized molecules was investigated. The Osiris and Molinspiration Cheminformatics programs, utilizing in silico analyses, imply that these naphthoquinones are candidates for use as drugs which was reinforced by the outcomes of the in vitro antifungal and trypanocidal activity tests. Our in vitro data indicated a MIC value of 8 μg mL-1 against Candida albicans ATCC 24433 strains, and an EC50 of 0.67 μM with respect to trypanocidal activity against Trypanosoma cruzi epimastigote strains (Y).

Aryl-free radical-mediated oxidative arylation of naphthoquinones using o-iodoxybenzoic acid and phenylhydrazines and its application toward the synthesis of benzocarbazoledione

Oxidative arylation of naphthoquinones has been developed through combination of o-iodoxybenzoic acid with arylhydrazines under mild conditions at open atmosphere. Arylated naphthoquinones with different electronic properties were obtained in moderate to good yields. The postulated radical mediated mechanism is supported by radical trapping experiments. Developed protocol for direct arylation of naphthoquinones has been extended toward short, high yielding, and an effective synthesis of antitumor-antibiotic precursor such as benzocarbazoledione.

Discovery and development of an efficient process to atovaquone

The discovery and development of an efficient and more sustainable manufacturing route to the antipneumocystic agent atovaquone (2-((1R,4R)-4-(4-chlorophenyl)cyclohexyl)-3-hydroxynaphthalene-1,4-dione) 1 is described. The existing commercial route to atovaquone delivers a poor yield of product and uses expensive reagents. The new synthesis commences with readily available phthalic anhydride, which is converted to 1,4-isochromandione 5 and then to atovaquone 1 by reaction with 4-(4-chlorophenyl)cyclohexanecarboxylic acid 3 using key bromination, Rosenmund reduction, and rearrangement chemistries. Downstream processing to atovaquone is both high yielding and robust, and the resulting process has been demonstrated on 200-kg scale. The process is simple, uses cheap raw materials, and is more sustainable in that it avoids lowyielding silver-promoted chemistry and isomerisation procedures. It includes a robust, facile, and highly efficient procedure to 1,4-isochromandione 5, and routes to 4-(4-chlorophenyl)cyclohexanecarboxaldehyde 9 have also been developed, including a Rosenmund method that was demonstrated on pilot-plant scale. Also discussed are the route-derived impurities and processing amendments to control their formation.

Arylation of lawsone through BF3-mediated coupling of its phenyliodonium ylide with activated arenes and aromatic aldehydes

Phenyliodonium ylide of lawsone, activated by BF3·Et 2O, reacts with electron-rich arenes to afford the corresponding 2-aryl-3-hydroxy-1,4-naphthoquinones, in a coupling reaction without metal catalysts. The same type of products, in greater variety and higher yields, are obtained from the reaction of the BF3·Et2O- activated ylide with aromatic aldehydes in a synthetically and mechanistically interesting deformylation reaction.

Expedient synthesis of 3-hydroxyisoquinolines and 2-hydroxy-1,4- naphthoquinones via one-pot aryne acyl-alkylation/condensation

A convenient method is disclosed for the synthesis of both 3-hydroxyisoquinolines and 2-hydroxy-1,4-naphthoquinones from β-ketoesters using a one-pot aryne acyl-alkylation/condensation procedure. When performed in conjunction with a one-step method for the synthesis of the β-ketoester substrates, this method provides a new route to these polyaromatic structures in only two steps from commercially available carboxylic acid starting materials. The utility of this approach is demonstrated in the synthesis of the atropisomeric P,N-ligand, QUINAP. The Royal Society of Chemistry 2009.