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Usage

Uses

Used in Dye Industry:
2,4-Dinitroacetanilide is used as an intermediate in the synthesis of various dyes, contributing to the development of a wide range of colorants for different applications.
Used in Pharmaceutical Industry:
2,4-Dinitroacetanilide is used as a building block in the production of certain pharmaceuticals, playing a crucial role in the synthesis of drugs that address various health conditions.
Used in Chemical Research:
2,4-Dinitroacetanilide is employed as a reagent in chemical research, facilitating the exploration of new chemical reactions and the development of novel compounds.

Upstream product

• 1563-87-7 N-acetyl-N-phenylacetamide 
• 108-24-7 acetic anhydride 
• 97-02-9 2,4-Dinitroanilin 
• 64-19-7 acetic acid 
• 103-84-4 Acetanilid 
• 552-32-9 o-nitroacetanilide 
• 128915-26-4 N-(2,4-Dinitro-phenyl)-N'-phenyl-acetamidine 
• 128915-25-3 N-(2,4-Dinitro-phenyl)-N'-p-tolyl-acetamidine 
• 128915-27-5 N-(4-Chloro-phenyl)-N'-(2,4-dinitro-phenyl)-acetamidine 
• 128915-24-2 N-(2,4-Dinitro-phenyl)-N'-(4-methoxy-phenyl)-acetamidine 
• 2754-27-0 trimethylsilyl acetate 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 13296-87-2 2,4-dinitrobenzamide 
• 104-04-1 N-(4-Nitrophenyl)acetamide 

Downstream Products

• 97-02-9 2,4-Dinitroanilin 
• 1792-40-1 2-methyl-5-nitrobenzimidazole 
• 53987-32-9 4-nitro-2-aminoacetanilide 
• 6373-15-5 acetic acid-(2,4-diamino-anilide) 
• 861295-75-2 acetic acid-(N-chloro-2,4-dinitro-anilide) 
• 91358-36-0 tetrabutylammonium salt of 2,4-dinitroacetanilide 
• 1792-40-1 6-nitro-2-methyl-1H-benzimidazole 
• 405314-01-4 1-hydroxy-2-methyl-6-nitrobenzimidazole 
• 3531-19-9 2-chloro-4,6-dinitroaniline 
• 99-56-9 4-Nitrophenylene-1,2-diamine 
• 6232-92-4 6-nitro-1H-benzo[d]imidazol-2-amine 

Relevant academic research and scientific papers

Transition-metal-free mono- or dinitration of protected anilines

An amide-assisted arene nitration is presented, and both mono- and dinitration of protected anilines could be effected by using NaNO2 and NaNO3 as the mono- and bisnitrating agents, respectively. This divergent synthesis is transition-metal- and acid-free, and features a broad substrate scope, low cost, and ortho–para selectivity.

1-Aryl-3-(4-methoxybenzyl)ureas as potentially irreversible glycogen synthase kinase 3 inhibitors: Synthesis and biological evaluation

Glycogen synthase kinase 3 (GSK-3)has become known for its multifactorial involvement in the pathogenesis of Alzheimer's disease. In this study, a benzothiazole- and benzimidazole set of 1-aryl-3-(4-methoxybenzyl)ureas were synthesised as proposed Cys199-targeted covalent inhibitors of GSK-3β, through the incorporation of an electrophilic warhead onto their ring scaffolds. The nitrile-substituted benzimidazolylurea 2b (IC50 = 0.086 ± 0.023 μM)and halomethylketone-substituted benzimidazolylurea 9b (IC50 = 0.13 ± 0.060 μM)displayed high GSK-3β inhibitory activity, in comparison to reference inhibitor AR-A014418 (1, IC50 = 0.072 ± 0.043)in our assay. The results suggest further investigation of 2b and 9b as potential covalent inhibitors of GSK-3β, since a targeted interaction might provide improved kinase-selectivity.

Conformational analysis of N-aryl-N-(2-azulenyl)acetamides

Aromatic amides bearing 2-azulenyl group on the amide nitrogen were synthesized and their structures were investigated. The π-electron density of the N-aryl group was found to influence the cis-trans conformational preferences of these compounds in solution. X-ray crystallography revealed that the plane of the 2-azulenyl ring has a strong tendency to lie coplanar with the amide plane when the azulene group is located on the same side as the amide oxygen atom.

Biogenic CuFe2O4 magnetic nanoparticles as a green, reusable and excellent nanocatalyst for acetylation reactions under solvent-free conditions

A convenient green method has been developed for the synthesis of biogenic CuFe2O4 magnetic nanoparticles using tea extracts within a very short reaction time. The prepared nanoparticles with an average size of 8.78 nm have been used as an effective catalyst for the acetylation of various alcohols, phenols and amines in good to excellent yields under solvent-free conditions. The catalyst was characterized by XRD, XPS, VSM, SEM and TEM study. A magnetic study of the fresh and recycled catalyst after the fourth cycle was performed by VSM measurement. The main advantages of this protocol are simple biogenic synthesis of the catalyst, a reusable and heterogeneous catalytic system, and short reaction times with excellent yields.

SO42-/SnO2: Efficient, chemoselective, and reusable catalyst for acylation of alcohols, phenols, and amines at room temperature

SO42-/SnO2 was employed for the acylation of a variety of alcohols, phenols, and amines under solvent-free conditions at room temperature. This method showed preferential selectivity for acetylation of the amino group in the presence of a hydroxyl group. The reported method is simple, mild, and environmentally viable, using several other acid anhydrides at room temperature. Copyright Taylor & Francis Group, LLC.

Acetylation of some organic compounds under microwave irradiation

Acetic acid has been used for acetylation of seven aromatic amines and two phenols under microwave exposure. The time taken for these reactions ranges from 18-25 min with reasonability good yields (65-77%).

On the active site for hydrolysis of aryl amides and choline esters by human cholinesterases

Cholinesterases, in addition to their well-known esterase action, also show an aryl acylamidase (AAA) activity whereby they catalyze the hydrolysis of amides of certain aromatic amines. The biological function of this catalysis is not known. Furthermore, it is not known whether the esterase catalytic site is involved in the AAA activity of cholinesterases. It has been speculated that the AAA activity, especially that of butyrylcholinesterase (BuChE), may be important in the development of the nervous system and in pathological processes such as formation of neuritic plaques in Alzheimer's disease (AD). The substrate generally used to study the AAA activity of cholinesterases is N-(2-nitrophenyl)acetamide. However, use of this substrate requires high concentrations of enzyme and substrate, and prolonged periods of incubation at elevated temperature. As a consequence, difficulties in performing kinetic analysis of AAA activity associated with cholinesterases have hampered understanding this activity. Because of its potential biological importance, we sought to develop a more efficient and specific substrate for use in studying the AAA activity associated with BuChE, and for exploring the catalytic site for this hydrolysis. Here, we describe the structure-activity relationships for hydrolysis of anilides by cholinesterases. These studies led to a substrate, N-(2-nitrophenyl)trifluoroacetamide, that was hydrolyzed several orders of magnitude faster than N-(2-nitrophenyl)acetamide by cholinesterases. Also, larger N-(2-nitrophenyl)alkylamides were found to be more rapidly hydrolyzed by BuChE than N-(2-nitrophenyl)acetamide and, in addition, were more specific for hydrolysis by BuChE. Thus, N-(2-nitrophenyl)alkylamides with six to eight carbon atoms in the acyl group represent suitable specific substrates to investigate further the function of the AAA activity of BuChE. Based on the substrate structure-activity relationships and kinetic studies, the hydrolysis of anilides and esters of choline appears to utilize the same catalytic site in BuChE.

Baker's yeast-mediated regioselective reduction of 2,4-dinitroacylanilines: Synthesis of 2-substituted 6-nitrobenzimidazoles

Several 2,4-dinitro-N-acylanilines were regioselectively reduced at the C-2 position by baker's yeast in slightly basic media (pH = 7.5) to afford 2-amino-4-nitroacylanilines, which were then cyclized under acidic conditions to the corresponding 2-substituted-6-nitrobenzimidazoles. The benzimidazoles thus obtained can be employed as precursors for bioactive derivatives.

Copper(II) Tetrafluoroborate-Catalyzed Acetylation of Phenols, Thiols, Alcohols, and Amines

Copper(II) tetrafluoroborate efficiently catalyzes acetylation of structurally diverse phenols, alcohols, thiols, and amines with stoichiometric amounts of Ac2O under solvent-free conditions at room temperature. Acid-sensitive alcohols are smoothly acetylated without competitive side reactions. The reaction is influenced by the steric and electronic factors associated with the substrate as well as the anhydride. Acetylation of a sterically hindered substrate requires excess of anhydride and longer time. Acylation with less electrophilic anhydrides affords poor to moderate yields.

Zirconiuni(IV) chloride as a new, highly efficient, and reusable catalyst for acetylation of phenols, thiols, amines, and alcohols under solvent-free conditions

Zirconium(IV) chloride has been found to be a new, highly efficient, and reusable catalyst for acetylation of structurally diverse phenols, thiols, amines, and alcohols under solvent-free condtions. Acetylation of sterically hindered and electron deficient phenols is achieved in excellent yields with stoichiometric amounts of Ac2O at room temperature. Acid-sensitive alcohols undergo acetylation with excellent chemoselectivity without competitive side reactions such as dehydration or rearrangement. The mild Lewis acid property of the catalyst enables the acetylation to be carried out with optically active substrates without any detrimental effect on the optical purity.