Aromatic Amino and Nitro–Amino Compounds and Their Halogenated Derivatives

Abstract

Aromatic amines are organic compounds that contain at least one amino group attached directly to an aryl moiety. Aromatic amines represent one of the most important classes of industrial and environmental chemicals. Many aromatic amines have been shown to be potent carcinogens, mutagens, skin sensitizers, and/or hematotoxicants capable of inducing methemoglobinemia. Since the introduction of substituted anilines and naphthylamines as intermediates for the manufacture of azo dyes in the mid‐1800s, aromatic amines have found numerous uses in various industries. Substantial worker exposure to aromatic amines with subsequent induction of bladder cancer occurred before preventive measures were instituted. Beyond occupational exposure, humans may also be exposed to aromatic amines through environmental sources. At least three carcinogenic aromatic amines (4‐aminobiphenyl, 2‐naphthylamine, and o ‐toluidine) have been detected in cigarette smoke. Many commonly used pharmaceuticals contain or are aromatic amines. Owing to their hazard potential, aromatic amines have been the subject of many biomonitoring studies, making them model compounds in molecular dosimetry and epidemiology studies. Since extensive information is available on the metabolic pathways and, to a lesser extent, the mechanism(s) of action, aromatic amines have also become targets for genetic polymorphism studies with ultimate goals of identifying susceptible subpopulations and designing of strategies for cancer prevention and intervention. The multifaceted interest in aromatic amines has continued to attract a tremendous amount of scientific studies and attention. Since the publication of the previous edition of Patty's on aromatic amines, many reviews and important research articles on aromatic amines and halogenated nitroaromatics have been published. In addition, a number of heterocyclic aromatic amines have attracted increasing attention as carcinogens of environmental significance. In this chapter, we present an overview of the aromatic amine class as a whole with emphasis on recent studies, followed by an updated description on individual chemicals grouped into eight subgroups of structurally related compounds.

In silico environmental risk assessment of fate and effects of pharmaceuticals and their TPs generated and treated by coupling tertiary processes in hospital wastewater

“…Aromatic amines undergo N-oxidation mediated by cytochrome P-450, with a series of reactions leading to the formation of the nitrenium ion, which is highly reactive towards DNA. 65,66 In addition to this alert, the Hacceptor-path3-Hacceptor SA was also observed for PCT TP9. PCT TP2 presented the N-methylol derivatives SA, reflecting hydrolysis with the release of formaldehyde, which can then attack DNA according to the Schiff base reaction mechanism.…”

In silico environmental risk assessment of fate and effects of pharmaceuticals and their TPs generated and treated by coupling tertiary processes in hospital wastewater

“…Aromatic amines undergo N-oxidation mediated by cytochrome P-450, with a series of reactions leading to the formation of the nitrenium ion, which is highly reactive towards DNA. 65,66 In addition to this alert, the Hacceptor-path3-Hacceptor SA was also observed for PCT TP9. PCT TP2 presented the N-methylol derivatives SA, reflecting hydrolysis with the release of formaldehyde, which can then attack DNA according to the Schiff base reaction mechanism.…”

Flower-Based Green Synthesis of Metallic Nanoparticles: Applications beyond Fragrance

“…Therefore, the reduction of these pollutants must be crucial. The 4-nitrophenol reduction product (i.e., 4-aminophenol)has been used as a mediator for paracetamol, sulfur dyes, rubber antioxidants, the making of black/white film developers, corrosion inhibitors, and precursors in antipyretic and analgesic drugs [112,113]. The use of NaBH 4 as a reductant and a metal catalyst for Au NPs, AgNPs, CuO NPs, and Pd NPs is the easiest and most effective approach to reduce 4-nitrophenol [114][115][116][117].…”

Reduction of 4-nitrophenol using green-fabricated metal nanoparticles

“…4,9,10 Therefore, the reduction of 4-NP to 4-aminophenol (4-AP) has become a crucial issue, given that 4-AP is a compound with a lower degree of toxicity. 6,11 Among the various 4-NP reduction reactions, the reaction with sodium borohydride (NaBH 4 ) as a reducing agent (H 2 source) in conjunction with metal catalysts, such as Pd, [12][13][14] Ag, 15,16 Pt, 8,17 Cu, 18 Au 4,9,19 and their assemblies on dendrimers, polymeric matrices, microgels, metal-immobilized silica-coated supports, and graphene oxide, 20 has gained more attention due to its eco-friendly and straightforward reduction process. Furthermore, chemical and green methods are widely employed for the fabrication of nanomaterials as catalysts for the 4-NP reduction reaction 21 in aqueous and semi-solid media.…”

“…In recent years, one issue that has generated signicant concern due to its adverse effects, mainly on human health, is the contamination of water (surface and groundwater), including the ocean. [1][2][3] The principal cause of this event is the high amounts of toxic and refractory pollutants, mainly 4-nitrophenol (4-NP), 1,[4][5][6] which is widely used in the pharmaceutical and textile industries 7,8 for the production of herbicides, insecticides, synthetic dyes, and paints, and as a corrosion inhibitor and pH indicator, among other applications. 4,9,10 Therefore, the reduction of 4-NP to 4-aminophenol (4-AP) has become a crucial issue, given that 4-AP is a compound with a lower degree of toxicity.…”

In silico environmental risk assessment of fate and effects of pharmaceuticals and their TPs generated and treated by coupling tertiary processes in hospital wastewater

“…Aromatic amines undergo N-oxidation mediated by cytochrome P-450, with a series of reactions leading to the formation of the nitrenium ion, which is highly reactive towards DNA. 65,66 In addition to this alert, the Hacceptor-path3-Hacceptor SA was also observed for PCT TP9. PCT TP2 presented the N-methylol derivatives SA, reflecting hydrolysis with the release of formaldehyde, which can then attack DNA according to the Schiff base reaction mechanism.…”

Flower-Based Green Synthesis of Metallic Nanoparticles: Applications beyond Fragrance

“…Therefore, the reduction of these pollutants must be crucial. The 4-nitrophenol reduction product (i.e., 4-aminophenol)has been used as a mediator for paracetamol, sulfur dyes, rubber antioxidants, the making of black/white film developers, corrosion inhibitors, and precursors in antipyretic and analgesic drugs [112,113]. The use of NaBH 4 as a reductant and a metal catalyst for Au NPs, AgNPs, CuO NPs, and Pd NPs is the easiest and most effective approach to reduce 4-nitrophenol [114][115][116][117].…”

Reduction of 4-nitrophenol using green-fabricated metal nanoparticles

“…4,9,10 Therefore, the reduction of 4-NP to 4-aminophenol (4-AP) has become a crucial issue, given that 4-AP is a compound with a lower degree of toxicity. 6,11 Among the various 4-NP reduction reactions, the reaction with sodium borohydride (NaBH 4 ) as a reducing agent (H 2 source) in conjunction with metal catalysts, such as Pd, [12][13][14] Ag, 15,16 Pt, 8,17 Cu, 18 Au 4,9,19 and their assemblies on dendrimers, polymeric matrices, microgels, metal-immobilized silica-coated supports, and graphene oxide, 20 has gained more attention due to its eco-friendly and straightforward reduction process. Furthermore, chemical and green methods are widely employed for the fabrication of nanomaterials as catalysts for the 4-NP reduction reaction 21 in aqueous and semi-solid media.…”

“…In recent years, one issue that has generated signicant concern due to its adverse effects, mainly on human health, is the contamination of water (surface and groundwater), including the ocean. [1][2][3] The principal cause of this event is the high amounts of toxic and refractory pollutants, mainly 4-nitrophenol (4-NP), 1,[4][5][6] which is widely used in the pharmaceutical and textile industries 7,8 for the production of herbicides, insecticides, synthetic dyes, and paints, and as a corrosion inhibitor and pH indicator, among other applications. 4,9,10 Therefore, the reduction of 4-NP to 4-aminophenol (4-AP) has become a crucial issue, given that 4-AP is a compound with a lower degree of toxicity.…”

In silico environmental risk assessment of fate and effects of pharmaceuticals and their TPs generated and treated by coupling tertiary processes in hospital wastewater

“…Aromatic amines undergo N-oxidation mediated by cytochrome P-450, with a series of reactions leading to the formation of the nitrenium ion, which is highly reactive towards DNA. 65,66 In addition to this alert, the Hacceptor-path3-Hacceptor SA was also observed for PCT TP9. PCT TP2 presented the N-methylol derivatives SA, reflecting hydrolysis with the release of formaldehyde, which can then attack DNA according to the Schiff base reaction mechanism.…”

Flower-Based Green Synthesis of Metallic Nanoparticles: Applications beyond Fragrance

“…Therefore, the reduction of these pollutants must be crucial. The 4-nitrophenol reduction product (i.e., 4-aminophenol)has been used as a mediator for paracetamol, sulfur dyes, rubber antioxidants, the making of black/white film developers, corrosion inhibitors, and precursors in antipyretic and analgesic drugs [112,113]. The use of NaBH 4 as a reductant and a metal catalyst for Au NPs, AgNPs, CuO NPs, and Pd NPs is the easiest and most effective approach to reduce 4-nitrophenol [114][115][116][117].…”

Reduction of 4-nitrophenol using green-fabricated metal nanoparticles

“…4,9,10 Therefore, the reduction of 4-NP to 4-aminophenol (4-AP) has become a crucial issue, given that 4-AP is a compound with a lower degree of toxicity. 6,11 Among the various 4-NP reduction reactions, the reaction with sodium borohydride (NaBH 4 ) as a reducing agent (H 2 source) in conjunction with metal catalysts, such as Pd, [12][13][14] Ag, 15,16 Pt, 8,17 Cu, 18 Au 4,9,19 and their assemblies on dendrimers, polymeric matrices, microgels, metal-immobilized silica-coated supports, and graphene oxide, 20 has gained more attention due to its eco-friendly and straightforward reduction process. Furthermore, chemical and green methods are widely employed for the fabrication of nanomaterials as catalysts for the 4-NP reduction reaction 21 in aqueous and semi-solid media.…”

“…In recent years, one issue that has generated signicant concern due to its adverse effects, mainly on human health, is the contamination of water (surface and groundwater), including the ocean. [1][2][3] The principal cause of this event is the high amounts of toxic and refractory pollutants, mainly 4-nitrophenol (4-NP), 1,[4][5][6] which is widely used in the pharmaceutical and textile industries 7,8 for the production of herbicides, insecticides, synthetic dyes, and paints, and as a corrosion inhibitor and pH indicator, among other applications. 4,9,10 Therefore, the reduction of 4-NP to 4-aminophenol (4-AP) has become a crucial issue, given that 4-AP is a compound with a lower degree of toxicity.…”