46492-08-4

Basic information

• Product Name: BENZ[G]ISOQUINOLINE-5,10-DIONE
• Synonyms: BENZ[G]ISOQUINOLINE-5,10-DIONE;2-aza-9,10-anthraquinone;benzo(g)isoquinoline-5,10-dione;2-Azaanthraquinone;3,4-Phthaloylpyridine;5,10-Dihydrobenzo[g]isoquinoline-5,10-dione;β-Anthrapyridinequinone;Bgid
• CAS NO: 46492-08-4
• Molecular Formula: C₁₃H₇NO₂
• Molecular Weight: 209.2
• Mol File: 46492-08-4.mol
• Article Data: 9

Chemical Properties

• Melting Point: 178-180 °C(lit.)
• Boiling Point: 407℃
• Flash Point: 202℃
• Appearance: /
• Density: 1.373
• Vapor Pressure: 7.77E-07mmHg at 25°C
• Refractive Index: 1.668
• PKA: 1.10±0.20(Predicted)
• CAS DataBase Reference: BENZ[G]ISOQUINOLINE-5,10-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZ[G]ISOQUINOLINE-5,10-DIONE(46492-08-4)
• EPA Substance Registry System: BENZ[G]ISOQUINOLINE-5,10-DIONE(46492-08-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 46492-08-4(Hazardous Substances Data)

Usage

General Description

Benz[g]isoquinoline-5,10-dione has been isolated as an active component from the ethanolic extract of the aerial parts of Mitracarpus scaber. It exhibits significant in vitro inhibitory activity against the AIDS-related pathogens. The in vitro antibacterial and anti-fungal activity of benz[g]isoquinoline-5,10-dione has been investigated using the agar well-diffusion assay.

InChI:InChI=1/C13H7NO2/c15-12-8-3-1-2-4-9(8)13(16)11-7-14-6-5-10(11)12/h1-7H

Upstream product

• 74975-25-0 4-benzoylpyridine-3-carboxylic acid 
• 50-46-4 isoquinoline-5,8-dione 
• 106-99-0 buta-1,3-diene 
• 137382-32-2 (2-carboxyphenyl)-(pyridin-3-yl)-ketone 
• 1165952-91-9 cyclohexa-1,3-diene 
• 607-32-9 5-nitroisoquinoline 
• 1034012-97-9 N-(tert-butoxycarbonyl)-2-(((2,2-dimethoxyethyl)amino)methyl)-1,4-naphthoquinone 
• 1034013-01-8 N-methanesulfonyl-(((1,4-dioxonaphth-2-yl)methyl)amino)acetaldehyde 
• 481-85-6 2-methyl-1,4-naphthohydroquinone 
• 53772-33-1 2-bromo-3-methyl-1,4-dimethoxynaphthalene 
• 58-27-5 menadione 
• 53772-19-3 1,4-dimethoxy-2-methylnaphthalene 
• 86489-90-9 2-bromo-3-(2-bromomethyl)-1,4-dimethoxynaphthalene 
• 626-55-1 3-Bromopyridine 

Relevant articles and documents

Synthesis and antitubercular activity of 1- and 3-substituted benzo[: G] isoquinoline-5,10-diones

In this study, a small library of twenty benzo[g]isoquinoline-5,10-diones were synthesized in a novel straightforward approach, starting from 2-methyl-1,4-naphthoquinone (vitamin K). An intramolecular Heck reaction of a N-vinylacetamide was a crucial step in the synthetic route, at which the combination of cesium carbonate and a bulky, electron rich trialkylphosphine (tBuCy2P.HBF4) provided high 6-endo-trig selectivity. The anti-tubercular activity against Mycobacterium tuberculosis H37Ra and acute cytotoxicity against J774 A.1 macrophages were studied. From the structure activity relationship, it could be derived that in general the substitution of position 3 yielded analogs with a higher antitubercular potency. Among these, two analogs, 27a and 27b, showed remarkable activity with minimal inhibition concentrations of respectively 28.92 μM and 1.05 μM, and acute cytotoxic concentrations of >128 μM and 34.85 μM. In addition, the analogs and their possible metabolites were evaluated using a Vitotox assay to study the possibility of genotoxicity. Results indicated that none of the evaluated analogs and their possible metabolites showed early signs of genotoxicity.

Isoquinoline compound and its preparation method, the organic electroluminescent device

The invention provides isoquinoline compounds and a preparation method thereof, and an organic light emitting diode. The isoquinoline compounds are as shown in a molecular formula (I) in the specification. Compared with the prior art, the isoquinoline compounds provided by the invention are prepared by introducing Q1, Q2, Ar1, Ar2, Ar3 and Ar4 groups into benzo[g]isoquinoline compounds, so electronic density and skills can be improved; meanwhile, R1 can improve performances of the isoquinoline compounds, so the organic light emitting diode containing the isoquinoline compounds as shown in the molecular formula (I) has the characteristics of high brightness, good heat resistance, long service life, high efficiency, etc.

Metallation of pyridines and quinolines in the presence of a remote carboxylate group. New syntheses of heterocyclic quinones

2-(3- and 2-Pyridylcarbonyl)benzoic acids (2,3), 2-(2-pyridylcarbonyl) thiophene-3-carboxylic acid (6), 2-(3-quinolylcarbonyl)benzoic acid (10), and most of the corresponding esters (compounds 1, 7 and 9) are readily synthesized and involved in a deprotonation-condensation sequence. Biologically active aza-anthraquinones such as benzo[g]isoquinoline-5,10-dione (2-azaanthraquinone, 4) and benzo[g]quinoline- 5,10-dione (1-azaanthraquinone, 5) are prepared using the strategy. Extension to other heterocyclic quinones such as thieno[3,2-g]quinoline-4,9-dione (8) and benzo[j]phenanthridine-7,12-dione (11) is also investigated.