188970-78-7

Basic information

• Product Name: 5-nitro-7H-dibenzo[c,g]carbazole
• Synonyms: 5-Nitro-7H-dibenzo[c,g]carbazole; 7H-dibenzo[c,g]carbazole, 5-nitro-
• CAS NO: 188970-78-7
• Molecular Formula: C₂₀H₁₂N₂O₂
• Molecular Weight: 312.3215
• Mol File: 188970-78-7.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 609°C at 760 mmHg
• Flash Point: 322.1°C
• Density: 1.445g/cm³
• Vapor Pressure: 4.01E-14mmHg at 25°C
• Refractive Index: 1.875
• CAS DataBase Reference: 5-nitro-7H-dibenzo[c,g]carbazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-nitro-7H-dibenzo[c,g]carbazole(188970-78-7)
• EPA Substance Registry System: 5-nitro-7H-dibenzo[c,g]carbazole(188970-78-7)

Safety Data

• Hazardous Substances Data: 188970-78-7(Hazardous Substances Data)

Usage

General Description

5-nitro-7H-dibenzo[c,g]carbazole, also known as N-7D, is a chemical compound with the molecular formula C20H11N3O2. It is classified as a heterocyclic aromatic amine and is a nitro-substituted polycyclic aromatic hydrocarbon. N-7D is a potent mutagen and is considered to be a potential human carcinogen. It is commonly found in environmental pollutants, including cigarette smoke, automobile exhaust, and industrial emissions. Exposure to N-7D has been linked to an increased risk of cancer, particularly in the lung, bladder, and liver. Due to its toxic and carcinogenic properties, efforts are being made to reduce environmental levels of N-7D and minimize human exposure to this hazardous compound.

Upstream product

• 64694-79-7 N-Acetyl-7H-dibenzo[c,g]carbazole 
• 859935-65-2 7-nitroso-7H-dibenzo[c,g]carbazole 
• 194-59-2 7H-dibenzo[c,g]carbazole 

Relevant articles and documents

Synthesis, characterization, and mutagenicity of nitrated 7H- dibenzo[c,g]carbazole and its phenolic derivatives

The nitrated N-heterocyclic aromatic hydrocarbons (NAHs) are found in a variety of environmental sources; many of them have been determined to be mutagenic in short-term assays and/or carcinogenic in animal tests. In this laboratory, we synthesized and characterized nitrated 7H- dibenzo[c,g]carbazole (DBC) and the nitrophenolic metabolites of DBC as potential mutagenic and carcinogenic xenobiotics. The nitro group was formed exclusively at the 5 and/or the symmetric 9 position of DBC, 2-hydroxy-DBC, 3-hydroxy-DBC, and 4-hydroxy-DBC. Ames plate incorporation mutagenicity assays were conducted using Salmonella typhimurium strains TA98 and TA100, with or without rat liver homogenates (S9). Mutagenicities of the nitrated DBCs were higher than the parent DBC in strain TA98. 5,9-Dinitro-DBC had stronger mutagenic responses than 5-nitro-DBC in all assays, particularly in strain TA98 with S9. 5,9-Dinitro-DBC had a higher reduction potential relative to 5-nitro-DBC (-1.09 V and -1.37 V, respectively). Hydroxyl derivatives of 5-nitro-DBC at the 2, 3, 4, 10, or 12 position, synthesized through nitration of the corresponding hydroxy-DBC, possessed greater mutagenicity than the parent 5-nitro-DBC, especially in strain TA100 with or without S9. Our data suggest that nitrated DBC undergoes both nitroreduction and ring oxidation as the primary pathways for the metabolic activation leading to mutagenesis. The relative mutagenicities of the nitrohydroxy-DBC isomers are generally consistent with the resonance stabilization of the positive charge at the arylnitrenium ion, formed from the nitro functional group, as the proposed active electrophile responsible for genotoxic effects.