54010-92-3

Basic information

• Product Name: 2-chloro-N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)acetamide
• CAS NO: 54010-92-3
• Molecular Formula: C₁₂H₇Cl₂NO₃
• Molecular Weight: 284.0949
• Mol File: 54010-92-3.mol

Chemical Properties

• Boiling Point: 456.6°C at 760 mmHg
• Flash Point: 229.9°C
• Density: 1.54g/cm³
• Vapor Pressure: 1.6E-08mmHg at 25°C
• Refractive Index: 1.63
• CAS DataBase Reference: 2-chloro-N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloro-N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)acetamide(54010-92-3)
• EPA Substance Registry System: 2-chloro-N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)acetamide(54010-92-3)

Safety Data

• Hazardous Substances Data: 54010-92-3(Hazardous Substances Data)

Upstream product

• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 2797-51-5 quinoclamine 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 132187-43-0 2-Chloracetylamino-3-(4-dimethylaminoanilino)-1,4-naphthochinon 
• 132187-46-3 2-Chloracetylamino-3-(4-iodanilino)-1,4-naphthochinon 
• 128691-45-2 2-Chlormethyl-1-(3-chlorphenyl)-4,9-dihydro-1H-naphtho<2,3-d>imidazol-4,9-dion 
• 128691-48-5 2-Chlormethyl-4,9-dihydro-1-(4-hydroxyphenyl)-1H-naphtho<2,3-d>imidazol-4,9-dion 
• 128691-44-1 2-Chlormethyl-1-(4-chlorphenyl)-4,9-dihydro-1H-naphtho<2,3-d>imidazol-4,9-dion 
• 128691-47-4 2-Chlormethyl-4,9-dihydro-1-(3-methylphenyl)-1H-naphtho<2,3-d>imidazol-4,9-ion 
• 128691-46-3 2-Chlormethyl-4,9-dihydro-1-(4-methylphenyl)-1H-naphtho<2,3-d>imidazol-4,9-dion 
• 132187-51-0 1,2,3,4,5,10-Hexahydro-4-(4-dimethylaminophenyl)benzochinoxalin-2,5,10-trion 
• 132187-50-9 1,2,3,4,5,10-Hexahydro-4-(4-methoxyphenyl)benzochinoxalin-2,5,10-trion 
• 132187-55-4 1,2,3,4,5,10-Hexahydro-4-(4-iodphenyl)benzochinoxalin-2,5,10-trion 
• 132187-54-3 4-(4-Bromphenyl)-1,2,3,4,5,10-hexahydrobenzochinoxalin-2,5,10-trion 
• 132187-52-1 4-(4-Fluorphenyl)-1,2,3,4,5,10-hexahydrobenzochinoxalin-2,5,10-trion 
• 132187-56-5 1,2,3,4,5,10-Hexahydro-4-(2-methylphenyl)benzochinoxalin-2,5,10-trion 
• 137660-79-8 2-Chloromethyl-4,9-dihydro-1-(2-methylphenyl)-1H-naphtho<2,3-d>imidazole-4,9-dion 

Relevant articles and documents

First electron transfer C-alkylation involving a fused quinoneimidazole reductive alkylating agent

The C-alkylation reaction of 2-chloromethyl-4,9-dihydro-1-methyl-1H-naphtho[2,3-d]imidazol-4,9-dion e by 2-nitropropane anion is shown to proceed by the S(RN)1 mechanism. This mechanism is confirmed by the inhibitory effects of dioxygen, p-dinitrobenzene, cupric chloride and TEMPO.

Diamine derivatives of quinone and uses thereof

Diamine derivatives of quinones, and related compounds, including salts thereof, that modulate the levels of gene expression in cellular systems, such as cancer cells, are disclosed, along with methods for preparing such compounds and derivatives, as well as pharmaceutical compositions containing these compounds and derivatives as active ingredients. Methods of using these as compounds and derivatives as therapeutic agents are also described.

Synthesis and antiplatelet, antiinflammatory, and antiallergic activities of 2-substituted 3-chloro-1,4-naphthoquinone derivatives

A series of 2-substituted 3-chloro-1,4-naphthoquinones was synthesized, and the antiplatelet, antiinflammatory, and antiallergic activities of these compounds were evaluated. The structure-activity relationships in this series were also examined. Most of the 2-alkyl/arylcarboxamido derivatives of 3-chloro-1,4-naphthoquinone showed potent activities with similar trends in each of the activities evaluated.

Preparation and in vitro antiprotozoan activity of new naphthoimidazolediones

The original compound bearing the coplanar quinone and imidazole systems, 2-chloromethyl-4,9-dihydro-1-methyl-1H-naphtho[2,3-d] imidazol-4,9-dione reacted with various nitronate anions to afford, in moderate to rood yields, new naphtho- imidazolediones bearing a trisubstituted ethylenic double bond at the 2-position. These compounds were evaluated as potential antiprotozoan agents. Some derivatives were found to have a significant activity, but the naphthoquinone was found to be a less efficient pharmacophore than the nitro group.

Synthesis and cytotoxicity of 1,2-disubstituted naphth[2,3-d]imidazole-4,9-diones and related compounds

As part of our continuing search for potential anticancer drug candidates that are selective against slowly growing solid tumors, we have synthesized several series of 1- and 2-substituted derivatives of the lead structure, 1-ethyl-2-methylnaphth[2,3-d]midazole-4,9-dione (5). Their cytotoxic activity in the National Cancer Institute's in vitro cancer cell line panel is reported. In general, substitution of various alkyl, phenyl, or benzyl moieties did not improve activity, and compound 5 remains the most active naphth[2,3-d]imidazole-4,9-dione derivative. However, high levels of activity and selectivity were found with several related 2-(acylamino)-3-chloro1,4-naphthoquinones (2f-j). Compound 2i, 2-[(2-fluorophenyl)acetamido]-3-chloro-1,4-naphthoquinone, has been selected for further in vivo testing and as an additional lead compound for further structural modification.