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Usage

Uses

Used in Dye Industry:
2,4-Dinitro-N,N-diethylaniline is used as a dye intermediate for the production of various dyes. Its unique chemical structure allows for the creation of a wide range of colors, making it a valuable component in the dye manufacturing process.
Used in Oil and Gas Industry:
In the oil and gas industry, 2,4-dinitro-N,N-diethylaniline is utilized as a corrosion inhibitor. Its ability to prevent the corrosion of pipelines and equipment helps to extend their lifespan and reduce maintenance costs, ensuring the smooth operation of the industry.
Used in Organic Synthesis:
2,4-Dinitro-N,N-diethylaniline serves as a starting material in the synthesis of various organic compounds. Its versatile chemical properties make it a valuable precursor for the production of a range of chemical products, including pharmaceuticals, agrochemicals, and other specialty chemicals.
However, due to its toxic nature and potential health risks, it is crucial to take proper precautions when handling or working with 2,4-dinitro-N,N-diethylaniline. This includes using appropriate personal protective equipment, ensuring proper ventilation, and following safety guidelines to minimize exposure and potential health hazards.

InChI:InChI=1/C10H13N3O4/c1-3-11(4-2)9-6-5-8(12(14)15)7-10(9)13(16)17/h5-7H,3-4H2,1-2H3

Upstream product

• 5429-28-7 4-(diethylamino)benzoic acid 
• 584-48-5 2,4-dinitrobromobenzene 
• 109-89-7 diethylamine 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 91-66-7 N,N-diethylaniline 
• 1184-78-7 trimethylamine-N-oxide 
• 121-44-8 triethylamine 
• 68-12-2 N,N-dimethyl-formamide 
• 5351-04-2 3-diethylaminopropionitrile 
• 70-34-8 2,4-Dinitrofluorobenzene 
• 617-84-5 N-formyldiethylamine 
• 685-91-6 diethylacetamide 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 

Downstream Products

• 3846-50-2 2,4-dinitro-N-ethylaniline 
• 46161-15-3 N¹,N¹,diethyl-benzene-1,2,4-triyltriamine 
• 857596-68-0 N-ethyl-2,4-dinitro-N-nitroso-aniline 
• 109-89-7 diethylamine 
• 51-28-5 2,4-Dinitrophenol 
• 97-02-9 2,4-Dinitroanilin 

Relevant academic research and scientific papers

Photoredox catalyzed dealkylative aromatic halogen substitution with tertiary amines

A reaction of aromatic halides bearing electron-withdrawing groups with tertiary amines in the presence of an iridium catalyst under blue light irradiation is described. Products of the aromatic substitution of the halide by the dialkylamino fragment are

Synthesis of o-Nitroarylamines via Ipso Nucleophilic Substitution of Sulfonic Acids

A mild, efficient, and eco-friendly method for the synthesis of o-nitroarylamine from o-nitroaryl sulfonic acid via ipso nucleophilic aryl substitution by amine is described. The products have been obtained with good yields at room temperature without the assistance of any metal, activating agent, or toxic oxidant. This method is useful for racemization-free synthesis of N-aryl amino acid esters.

Understanding the effects of solvate ionic liquids as solvents on substitution processes

The effects of solvate ionic liquids as solvents have been considered for two substitution processes where the solvent effects of typical ionic liquids have been extensively investigated previously; the bimolecular nucleophilic substitution (SN

“Zero VOC” Synthetic Strategy – Aromatic Amination Reactions in Deep Eutectic Solvents

Rising concern for environment hazards resulting from the use of volatile organic compounds (VOCs) is prompting many chemists to use “green” solvents like water, polyethylene glycol, ionic liquids and deep eutectic solvents (DES). With a few notable exceptions, many of these processes still need to use volatile organic solvents for the workup and isolation of products. In the present report, we demonstrate a “zero VOC” protocol which eliminates the need to use organic solvents for any stage of the reaction. As a proof of concept, nucleophilic aromatic substitution reactions of 1-halo-2,4-dinitrobenzene with secondary amines were carried out in deep eutectic solvents. The reaction workup involved the addition of water for separating the product from the DES. Evaporation of water led to recovery of the DES, which exhibited good recyclability. The reaction in deep eutectic solvents was much faster than that in many other solvents, as confirmed by the kinetic studies. An attempt was made to elucidate the origin of this rate enhancement based on analysis activation parameters and correlation with the polarity parameters. The results show that use of deep eutectic solvents can take chemists a step closer towards the “zero VOC” synthetic strategy.

Mechanistic assessment of SNAr displacement of halides from 1-Halo-2,4-dinitrobenzenes by selected primary and secondary amines: Br?nsted and Mayr analyses

Pseudo-first-order rate constants (kobsd) have been measured spectrophotometrically for nucleophilic substitution reactions of 1-X-2,4-dinitrobenzenes (1a-d, X = F, Cl, Br, I) with various primary and secondary amines in MeCN and H2O

Reaction products of activated aromatic and heteroaromatic chlorides with n,n-disubstituted formamides

Several N,N-disubstituted aromatic amines (3a-g) was obtained in very good yield by the reaction of adequate doubly activated aromatic or heteroaromatic halides (1a-e) with N,N-disubstituted formamides (2a-c). Analogously, starting from 4-chloro-3-pyridin

Regioselective nitration of N,N-dialkylanilines using cerium(IV) ammonium nitrate in acetonitrile

A highly regioselective and inexpensive nitration of N,N-dialkylanilines by cerium(IV) ammonium nitrate (CAN) in acetonitrile under room temperature to yield p-nitryl-N,N-dialkylanilines in good yields was reported.

The secondary amine/nitric oxide complex ion R2N[N(O)NO]- as nucleophile and leaving group in SNAr reactions

Ions of structure R2N[N(O)NO]- and their alkylation products have seen increasing use as nitric oxide (NO)-generating agents for biomedical research applications. Here we show that such diazeniumdiolate anions can readily displace halide from a variety of electrophilic aza- or nitroaromatic substrates to form O2-arylated derivatives of structure R2N-N(O)=N-OAr. The site of arylation and the cis arrangement of the oxygens were confirmed by X-ray crystallography. Displacement by various nucleophiles showed R2N[N(O)NO]- to be a reasonably good leaving group, with rate constants for displacement by hydroxide, methoxide, and isopropylamine that were between those of chloride and fluoride in the SNAr reactions we surveyed. The Meisenheimer intermediate could be spectrally observed. These O2-aryl diazeniumdiolates proved capable of reacting with the nucleophilic sulfur of the HIV-1 p7 nucleocapsid protein's zinc finger assembly to eject the zinc, disrupting a structural motif critical to viral replication and suggesting possible utility in the drug discovery realm.

OXIDATION DYES

The invention relates to oxidation colorants which are particularly suitable for coloring keratin fiber and to a method of coloring such fiber. The colorants contain as the preliminary oxidation dye at least one diamino aniline of the general formula (I), in which R1 to R6 independently of each other are hydrogen, a (C1-C4)-alkyl group, a hydroxy-(C2-C3)-alkyl group, a (C1-C4)-alkoxy-(C2-C3)-alkyl group, an amino-(C2-C3)-alkyl group in which the amino group can also have one or two (C1-C4)-alkyl radicals, or a 2,3-dihydroxypropyl group provided that not all substituents R1 to R6 are simultaneously hydrogen, and R1 and R2 and/or R3 and R4 and/or R5 and R6 along with the nitrogen atom to which they are attached are also an aziridine ring, an azetidine ring, a pyrrolidine ring, a piperidine ring, an azepane ring, an azocine ring or a morpholino group, thiomorpholino group or piperazino group which has another substituent R7 on the nitrogen atom which is selected from hydrogen, a (C1-C4)-alkyl group, a hydroxy-(C2-C3)-alkyl group, a (C1-C4)-alkoxy-(C2-C3)-alkyl group, an amino-(C2-C3)-alkyl group, or a 2,3-dihydroxypropyl group, and the three remaining hydrogen atoms on the benzol ring can also be replaced independently of each other by a halogen atom or a (C1-C4)-alkyl group, or the physiologically tolerable salts thereof with inorganic and organic acids. Shades of color are obtained which have a high level of brilliancy and color fastness.

15N NMR and FTIR studies of 2,4-dinitroanilines and their salts

Twenty-two 2,4-dinitroanilines were synthesised and their pK(a) values were determined. The 2,4-dinitroanilines and their protonated forms were studied by 15N NMR spectroscopy. The relations between the 15N NMR chemical shifts and the pK(a) values of the 2,4-dinitroanilines and their salts were found to be linear. The deprotonation reaction of N-methyl-2,4- dinitroanilines and N-methyl-2,4,6-trinitroaniline by MTBD was successful only for the latter and yielded protonated MTBD molecule and the anion in which the electrons are strongly delocalised. The kinetic parameters of the 2,4-dinitroanilines in reactions with hydroxide ions in mixed solvent DMSO:water (95:5, v/v) were determinated and discussed. (C) 2000 Elsevier Science B.V.