363-03-1

Basic information

• Product Name: PHENYL-P-BENZOQUINONE
• Synonyms: 2-Phenyl-[1,4]benzoquinone;2-Phenyl-1,4-benzoquinone;2-phenyl-2,5-cyclohexadiene-1,4-dione;2-Phenylbenzoquinone;2-phenyl-p-benzoquinon;4-dione,2-phenyl-5-cyclohexadiene-1;o-phenylbenzoquinone;p-Benzoquinone, 2-phenyl-
• CAS NO: 363-03-1
• Molecular Formula: C₁₂H₈O₂
• Molecular Weight: 184.19
• EINECS: 206-654-5
• Mol File: 363-03-1.mol
• Article Data: 55

Chemical Properties

• Melting Point: 111-115 °C
• Boiling Point: 278.14°C (rough estimate)
• Flash Point: 125.2°C
• Appearance: Yellow-brown/Chunks and Powder
• Density: 1.1336 (rough estimate)
• Vapor Pressure: 0.000133mmHg at 25°C
• Refractive Index: 1.6086 (estimate)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: PHENYL-P-BENZOQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: PHENYL-P-BENZOQUINONE(363-03-1)
• EPA Substance Registry System: PHENYL-P-BENZOQUINONE(363-03-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-42/43-20/21/22
• Safety Statements: 37/39-26-36
• RTECS: DK6650000
• Hazardous Substances Data: 363-03-1(Hazardous Substances Data)

Usage

Chemical Properties

Yellow-brown chunks and powder

Uses

Phenylquinone is used for small molecule-based targeting of TTD-A dimerization to control TFIIH transcriptional activity whichrepresents a potential strategy for anticancer therapy.

Synthesis Reference(s)

Journal of the American Chemical Society, 118, p. 2509, 1996 DOI: 10.1021/ja954009q

Safety Profile

Poison by intraperitoneal route. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes

Purification Methods

Crystallise the quinone from heptane, pet ether (b 60-70o), *C6H6 (m 113.5-114.5o) or EtOH (m 112-113o) and sublime it in vacuo. [Carlson & Miller J Am Chem Soc 107 479 1985, Beilstein 7 H 740, 7 III 3764.]

InChI:InChI=1/C12H8O2/c13-10-6-7-12(14)11(8-10)9-4-2-1-3-5-9/h1-8H

Upstream product

• 90-41-5 2-phenylaniline 
• 67-56-1 methanol 
• 42860-77-5 4-hydroxy-4-phenyl-cyclohexa-2,5-dienone 
• 7664-93-9 sulfuric acid 
• 92-69-3 4-Phenylphenol 
• 106-51-4 p-benzoquinone 
• 71-43-2 benzene 
• 591-50-4 iodobenzene 
• 64-17-5 ethanol 
• 127-09-3 sodium acetate 
• 108-05-4 vinyl acetate 
• 98-80-6 phenylboronic acid 
• 100-63-0 phenylhydrazine 
• 123-31-9 hydroquinone 

Downstream Products

• 65254-20-8 (+/-)-5.8-dioxo-6-phenyl-(4arH.8acH)-1.4.4a.5.8.8a-hexahydro-1c.4c-methano-naphthalene 
• 102661-81-4 2-[2]naphthyl-5-phenyl-[1,4]benzoquinone 
• 16793-13-8 3,3-dimethyl-2-morpholin-4-yl-6-phenyl-2,3-dihydro-benzofuran-5-ol 
• 16793-15-0 3,3-dimethyl-2-morpholin-4-yl-7-phenyl-2,3-dihydro-benzofuran-5-ol 
• 60457-33-2 5,6-Di-cyclohepta-2,4,6-trienyl-2-phenyl-cyclohex-2-ene-1,4-dione 
• 60457-32-1 C₁₉H₁₆O₂ 
• 127245-01-6 2-Benzyl-7-phenyl-benzofuran-5-ol 
• 108046-77-1 2-Methyl-1,3,4-triphenyl-2H-isoindole-4,7-dione 
• 1079-21-6 Phenylhydroquinone 
• 2887-97-0 2,6-diphenyl-[1,4]benzoquinone 
• 844-51-9 2,5-diphenyl-p-benzoquinone 
• 988-29-4 2,3,5,6-tetraphenyl-p-benzoquinone 
• 22954-61-6 triphenyl-[1,4]benzoquinone 
• 71329-17-4 2,3-diphenyl-benzoquinone 

Relevant articles and documents

Synthesis of phenyl-substituted conduritol B and its mechanism of formation

The phenyl-substituted conduritol B 8 was prepared in racemic form in a five-step sequence starting from 2-phenyl-1,4-benzoquinone (10) (Scheme 1). The reaction mechanism of the key step 12b → 13 is discussed (Scheme 2).

Selective Palladium-Catalyzed α,β-Homodiarylation of Vinyl Esters in Aqueous Medium

A palladium-catalyzed 1,2-diarylation of vinyl esters with arylboronic acids in water has been developed. This newly elaborated protocol features a good functional group tolerance and provides one-step access to 1,2-diarylethanol derivatives under mild reaction conditions. The presented reaction can be carried out in the water at ambient temperature without the addition of any ligands, what makes this procedure environmentally benign. The transformation occurs within a single catalytic cycle and is feasible due to the modification of transition metal catalytic activity through the influence of π-acceptor olefin (benzoquinone) as well as water as a medium. Moreover, this protocol allows to generate entire compound libraries (highly profitable in medicinal chemistry) and utilizes sustainable arylboronic acids as coupling partners under mild conditions. It is also noted that the structure of boron moiety has a great impact on the reaction selectivity, the usage of sterically hindered esters of arylboronic acids influence the reaction course towards stilbenes.

Strategies towards potent trypanocidal drugs: Application of Rh-catalyzed [2?+?2?+?2] cycloadditions, sulfonyl phthalide annulation and nitroalkene reactions for the synthesis of substituted quinones and their evaluation against Trypanosoma cruzi

Rhodium-catalyzed [2 + 2 + 2] cycloadditions, sulfonyl phthalide annulations and nitroalkene reactions have been employed for the synthesis of 56 quinone-based compounds. These were evaluated against Trypanosoma cruzi, the parasite that causes Chagas disease. The reactions described here are part of a program that aims to utilize modern, versatile and efficient synthetic methods for the one or two step preparation of trypanocidal compounds. We have identified 9 compounds with potent activity against the parasite; 3 of these were 30-fold more potent than benznidazole (Bz), a drug used for the treatment of Chagas disease. This article provides a comprehensive outline of reactions involving over 120 compounds aimed at the discovery of new quinone-based frameworks with activity against T. cruzi.