7403-75-0

Usage

Uses

Used in Organic Synthesis:
3-Nitro-4-acetamidophenol is used as a synthetic intermediate for the production of a wide range of organic compounds. Its unique chemical structure allows it to be a versatile building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
Within the pharmaceutical industry, 3-Nitro-4-acetamidophenol is utilized as a key component in the development of new drugs. Its reactivity and structural properties make it suitable for the synthesis of various drug candidates, potentially leading to the discovery of novel therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, 3-Nitro-4-acetamidophenol is employed as a starting material for the synthesis of pesticides and other crop protection agents. Its use in this industry contributes to the development of more effective and environmentally friendly solutions for agricultural challenges.
Used in Dye and Pigment Industry:
3-Nitro-4-acetamidophenol is also used as a precursor in the production of dyes and pigments. Its yellow solid form can be further modified to create a variety of colors, which are then used in various applications such as textiles, plastics, and printing inks.
Used in Research and Development:
Due to its unique chemical properties, 3-Nitro-4-acetamidophenol is often utilized in research and development settings. Scientists and chemists use 3-NITRO-4-ACETAMIDOPHENOL to study various chemical reactions and to develop new methodologies for organic synthesis, potentially leading to advancements in the field of chemistry.

InChI:InChI=1/C8H8N2O4/c1-5(11)9-7-3-2-6(12)4-8(7)10(13)14/h2-4,12H,1H3,(H,9,11)

Upstream product

• 2243-69-8 4-acetamido-3-nitrophenyl acetate 
• 610-81-1 4-hydroxy-2-nitroaniline 
• 108-24-7 acetic anhydride 
• 103-90-2 4-acetaminophenol 
• 50700-49-7 N-acetyl-p-benzoquinoneimine 
• 7664-93-9 sulfuric acid 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 2623-33-8 4-acetoxyacetanilide 
• 103-84-4 Acetanilid 

Downstream Products

• 608-71-9 Pentabromophenol 
• 610-81-1 4-hydroxy-2-nitroaniline 
• 99233-28-0 4-acetamino-2,3-dinitrophenol 
• 871878-62-5 acetic acid-(4-hydroxy-2,5-dinitro-anilide) 
• 871894-87-0 N-(4-hydroxy-3,5,6-trinitrophenyl)acetamide 
• 67694-84-2 N-(2-amino-4-hydroxyphenyl)acetamide 
• 105906-40-9 acetic acid-[4-(3-bromo-propoxy)-2-nitro-anilide] 
• 111992-31-5 1,3-bis-(4-acetylamino-3-nitro-phenoxy)-propane 
• 117013-72-6 2-<(4-acetamido-3-nitro-phenoxy)-methyl>-1,3-dioxolane 
• 75258-07-0 1,2-diacetamido-4-acetoxybenzene 
• 629622-05-5 4-[(2-ethynyltricyclo[3.3.1.1^3,7]decan-2-yl)oxy]-2-nitro-acetamide 
• 152538-17-5 N-[4-(4-chlorobutoxy)-2-nitrophenyl]acetamide 
• 875923-68-5 N-[4-(6-chlorohexyloxy)-2-nitrophenyl]acetamide 
• 875923-67-4 N-[4-(5-chloropentyloxy)-2-nitrophenyl]acetamide 

Relevant academic research and scientific papers

Acylamino-Directed Specific Sequential Difunctionalizations of Anilides via Metal-Free Relay Reactions for p-Oxygen and o-Nitrogen Incorporation

Novel acylamino-directed relay disubstitutions realize the sequential difunctionalizations of anilides (1) under mild and metal-free conditions for the first time. This [bis(trifluoroacetoxy)iodo]benzene (PIFA) and BF3·Et2O promoted straightforward reaction produces a series of p-acetoxyl- or p-alkoxyl-o-nitro-N-arylamides (2), which are key scaffolds of various drugs, functional materials, and bioactive molecules. The flexibility with respect to the functional groups in these products affords this novel protocol excellent versatility for synthetic applications.

Silver-Catalyzed Chemo- and Regioselective Nitration of Anilides

A new and efficient Ag-catalyzed method for the nitration of anilides by using sodium nitrite as a cheap and available NO2 source has been developed. This C–H functionalization reaction is ortho-selective, achieves moderate to high yields and shows excellent functional group tolerance. Furthermore, it provides a novel approach to ortho-nitrated anilides, which are very tricky to access with traditional methods.

Regioselective Green Electrochemical Approach to the Synthesis of Nitroacetaminophen Derivatives

A regioselective green synthesis of nitroacetaminophen derivatives was carried out by electrochemical oxidation of acetaminophen, N-(2-hydroxyphenyl)acetamide, and 1-(4-(4-hydroxyphenyl)piperazin-1-yl)ethanone in the presence of nitrite ion as a nucleophile. The present work has led to the development of a reagentless green and facile electrochemical method for the synthesis of some nitroacetaminophen derivatives.

Mizoroki-heck reactions with 4-phenoldiazonium salts

Significantly better yields were achieved in Mizoroki-Heck reactions using 4-phenoldiazonium salts instead of their O-alkylated analogues under otherwise identical conditions. We found that a one-flask deacetylation-diazotation- precipitation sequence starting from paracetamol or acetanilides derived thereof provides a convenient access to the required diazonium tetrafluoroborates. The utility of these arylating agents in palladium-catalyzed C-C bond forming reactions was demonstrated for a one-flask-synthesis of the heterocyclic core of the drug aripiprazole. Notably, the diazonium salt formation from an acetanilide could be combined with two Pd-catalyzed steps in a one-flask sequence, without any exchange of solvents or isolation of intermediates.

Reductive cyclization with baker's yeast of 4-alkyl-2-nitro-acetanilides to 6-alkylbenzimidazoles and 1-hydroxy-2-methyl-6-alkylbenzimidazoles

Reduction of 4-substituted 2-nitroacetanilides by baker's yeast in acid media effected cyclization, resulting in the formation of n-substituted 2-methylbenzimidazoles and 6-substituted 1-hydroxy-2-methylbenzimidazole via the chemo- and regioselective reduction of the 2-nitro aromatic group to amine or hydroxylamine.

Mild, efficient and selective nitration of anilides, non-activated and moderately activated aromatic compounds with ammonium molybdate and nitric acid as a new nitrating agent

Ammonium molybdate [Mo(VI)] is operationally simple, environmentally safe and inexpensive reagent. Regioselective nitration of anilides, non-activated and moderately activated aromatic compounds could be afforded by employing ammonium molybdate and nitric acid as mild and effective nitrating agent. This procedure works efficiently under reflux conditions to prepare mononitroderivatives of anilides, non-activated and moderately activated aromatic compounds in good to excellent yield with high regioselectivity.

A New Synthetic Route to 6,7-Dichloro-5,8-quinoxalinedione and Synthesis of Its Derivatives

6,7-Dichloro-5,8-quinoxalinedione (2), an analogue of Dichlone, was prepared from 4-aminophenol (3) in 27percent overall yield in 8 steps via chloroxidation of the sulfuric acid salt of 8-amino-5-quinoxalinol (9) as a key step.And two derivatives, 6-chloro-5-hydroxypyrazinophenazine (10) and pyridoimidazoquinoxaline-6,11-dione (11), were prepared by reaction of 2 with 1,2-phenylenediamine and 2-aminopyridine in 79percent and 46percent yields, respectively.

A NEW NITRATION PRODUCT, 3-NITRO-4-ACETAMIDOPHENOL, OBTAINED FROM ACETAMINOPHEN WITH NITROUS ACID

Treatment of acetaminophen with an excess sodium nitrite under mildly acidic to neutral conditions results in smooth formation of new 3-nitro-4-acetamidophenol via N-acetyl-p-benzoquinone imine as an oxidation intermediate, which is a well-known, widely e