144511-13-7

Basic information

• Product Name: 6,9-difluorobenzoisoquinoline-5,10-dione
• Synonyms: 6,9-difluorobenzoisoquinoline-5,10-dione;6,9-Difluorobenzo[g]isoquinolin-5,10-dione;6,9-difluorobenzoisoquinoline-5,10-dione;6,9-difluorobenzo;Pixantrone pharMaceutical interMediate;6,9-Difluorobenz[g]isoquinoline-5,10-dione;PSQ04
• CAS NO: 144511-13-7
• Molecular Formula: C₁₃H₅F₂NO₂
• Molecular Weight: 245.1811064
• Mol File: 144511-13-7.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 433℃
• Flash Point: 215℃
• Appearance: /
• Density: 1.525
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -0.58±0.20(Predicted)
• CAS DataBase Reference: 6,9-difluorobenzoisoquinoline-5,10-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 6,9-difluorobenzoisoquinoline-5,10-dione(144511-13-7)
• EPA Substance Registry System: 6,9-difluorobenzoisoquinoline-5,10-dione(144511-13-7)

Safety Data

• Hazardous Substances Data: 144511-13-7(Hazardous Substances Data)

Usage

General Description

6,9-difluorobenzoisoquinoline-5,10-dione is a chemical compound that belongs to the class of benzoisoquinoline-5,10-dione derivatives. It is composed of a benzene ring fused to an isoquinoline ring, with fluorine atoms at the 6 and 9 positions. 6,9-difluorobenzoisoquinoline-5,10-dione has potential applications in the field of pharmaceuticals and organic synthesis due to its unique structure and chemical properties. Its molecular structure and reactivity make it a promising candidate for drug development and as a building block for the synthesis of new organic compounds. Further research and exploration of its chemical properties may lead to the discovery of novel applications and uses for 6,9-difluorobenzoisoquinoline-5,10-dione.

Upstream product

• 4664-08-8 cinchomeronic anhydride 
• 540-36-3 para-difluorobenzene 
• 144511-12-6 3-(2',5'-difluorobenzoyl)isonicotinic acid 
• 144511-11-5 4-(2',5'-Difluorobenzoyl)nicotinic acid 
• 490-11-9 3,4-pyridinecarboxylic acid 
• 188622-59-5 3-(2,5-Difluoro-benzyl)-isonicotinic acid 
• 626-60-8 3-Chloropyridine 
• 111608-80-1 4,7-difluoro-3-cyano-1(3H)-isobenzofuranone 

Downstream Products

• 144510-94-1 6,9-bis<<2-ethyl>amino>benzoisoquinoline-5,10-dione 
• 145047-56-9 6,9-bis<<2-(dimethylamino)ethyl>amino>benzoisoquinoline-5,10-dione 2-oxide 
• 188964-72-9 2-<2--N-(2-hydroxyethyl)amino>ethyl>-5-<<(4-methylphenyl)sulfonyl>oxy>indazolo<4,3-gh>isoquinolin-6(2H)-one 
• 156090-04-9 2-[2-(N-tert-butoxycarbonylamino)ethyl]-5-(p-toluenesulfonyloxy)-isoquino[8,7,6-cd]indazole-6(2H)-one 
• 220074-31-7 2-<2--N-methylamino>ethyl>-5-<<(4-methylphenyl)sulfonyl>oxy>indazolo<4,3-gh>isoquinolin-6(2H)-one 
• 156090-05-0 2-<2-<(2-hydroxyethyl)amino>ethyl>-5-<<(4-methylphenyl)sulfonyl>oxy>indazolo<4,3-gh>isoquinolin-6(2H)-one 
• 220074-30-6 2-<3-(dimethylamino)propyl>-5-<<(4-methylphenyl)sulfonyl>oxy>indazolo<4,3-gh>isoquinolin-6(2H)-one 
• 156090-03-8 2-<2-(dimethylamino)ethyl>-5-<<(4-methylphenyl)sulfonyl>oxy>indazolo<4,3-gh>isoquinolin-6(2H)-one 
• 156090-18-5 5-[[2-(dimethylamino)ethyl]amino]-2-[2-[(2-hydroxyethyl)amino]ethyl]indazolo[4,3-gh]isoquinolin-6(2H)-one dihydrochloride 
• 172779-22-5 2-(2-hydroxyethyl)-5-<<(4-methylphenyl)sulfonyl>oxy>indazolo<4,3-gh>isoquinolin-6(2H)-one 
• 156090-75-4 9-fluoro-6-<<(4-methylphenyl)sulfonyl>oxy>benzisoquinoline-5,10-dione 
• 144510-89-4 6,9-bis<<2-(diethylamino)ethyl>amino>benzoisoquinoline-5,10-dione 

Relevant articles and documents

Synthesis of fluorine-substituted anthraquinones and azaanthraquinones

Using 1,4-dipolar-aryne cycloaddition methodology, a convenient, short synthesis of several fluoroanthraquinones is presented which involves the reaction of haloarenes and 3-cyanophthalides in the presence of lithium diisopropylamide (LDA) in tetrahydrofuran (THF).The fluorine substituent(s) can be introduced by using fluorine-substituted haloarenes and/or 3-cyanophthalides.Similarly, fluorine-substituted pyridines can be prepared by treating fluorine-substituted cyanophthalides and halopyridines in the presence of lithium diisopropylamide.

New anthracenedione derivatives with improved biological activity by virtue of stable drug-DNA adduct formation

Mitoxantrone is an anticancer agent that acts as a topoisomerase II poison, however, it can also be activated by formaldehyde to form DNA adducts. Pixantrone, a 2-aza-anthracenedione with terminal primary amino groups in its side chains, forms formaldehyde-mediated adducts with DNA more efficiently than mitoxantrone. Molecular modeling studies indicated that extension of the "linker" region of anthracenedione side arms would allow the terminal primary amino greater flexibility and thus access to the guanine residues on the opposite DNA strand. New derivatives based on the pixantrone and mitoxantrone backbones were synthesized, and these incorporated primary amino groups as well as extended side chains. The stability of DNA adducts increased with increasing side chain length of the derivatives. A mitoxantrone derivative bearing extended side chains (7) formed the most stable adducts with ～100-fold enhanced stability compared to mitoxantrone. This finding is of great interest because long-lived drug-DNA adducts are expected to perturb DNA-dependent functions at all stages of the cell cycle.

Synthesis of regioisomeric 6,9-(chlorofluoro)-substituted benzo[g]quinoline-5,10-diones, benzo[g]isoquinoline-5,10-diones and 6-chloro-9-fluorobenzo[g]quinoxaline-5,10-dione

Treatment of difluoro or chloro fluoro-substituted benzyl bromides 5a-c with zinc dust in tetrahydrofuran leads to the corresponding benzylic zinc bromides 6a-c. These organometallics on treatment with chlorosubstituted heterocyclic esters 4A and 4B mediated by nickel catalysis undergo couplings to yield dihalobenzyl substituted heterocyclic esters 7Aa-c and 7Ba-c. Treatment of 4c with 6c under Pd catalysis leads to 7Cc. The acids 8, prepared by hydrolysis of these esters, with treatment of fuming sulfuric acid undergo cyclizations and oxidations to yield the desired regioisomeric dihalo-substituted heterocyclic quinones 2.