528-75-6

Usage

Uses

1. Used in Organic Synthesis:
2,4-Dinitrobenzaldehyde is used as a reagent in the preparation of Schiff bases, which are essential intermediates in the synthesis of various organic compounds, including pharmaceuticals, dyes, and other specialty chemicals. Schiff bases are formed by the condensation of an amine with an aldehyde or ketone, and the presence of the nitro groups in 2,4-dinitrobenzaldehyde allows for the formation of stable and versatile Schiff base derivatives.
2. Used in Analytical Chemistry:
Due to its unique chemical properties, 2,4-dinitrobenzaldehyde can be employed as a reagent in analytical chemistry for the detection and quantification of various compounds. For instance, it can be used to identify primary amines through the formation of colored Schiff bases, which can then be analyzed spectrophotometrically.
3. Used in the Pharmaceutical Industry:
In the pharmaceutical industry, 2,4-dinitrobenzaldehyde can be utilized as a starting material for the synthesis of various therapeutic agents. Its ability to form Schiff bases with amines makes it a valuable building block for the development of novel drugs with potential applications in treating various diseases and medical conditions.
4. Used in the Dye Industry:
The versatility of 2,4-dinitrobenzaldehyde in forming Schiff bases also makes it a valuable compound in the dye industry. The resulting colored complexes can be used to produce a wide range of dyes with different shades and hues, which can be applied in various industries such as textiles, plastics, and printing.
5. Used in the Research and Development of New Materials:
The unique chemical properties of 2,4-dinitrobenzaldehyde also make it a valuable compound in the research and development of new materials. Its ability to form stable complexes with various organic and inorganic compounds can lead to the discovery of new materials with unique properties and potential applications in various fields, such as electronics, energy storage, and environmental remediation.

InChI:InChI=1/C7H4N2O5/c10-4-5-1-2-6(8(11)12)3-7(5)9(13)14/h1-4H

Upstream product

• 121-14-2 2,4-dinitrotoluene 
• 871876-73-2 2,3-dimethyl-4-nitroso-aniline 
• 80352-47-2 1-(2,4-dinitro-benzyl)-pyridinium; iodide 
• 27402-30-8 5-(2,4-dinitro-benzylidene)-pyrimidine-2,4,6-trione 
• 110449-10-0 5-(2',4'-dinitrobenzylidene)-1,3-dimethylbarbituric acid 
• 37951-28-3 2,2',4,4'-tetranitrostilbene 
• 861529-65-9 N¹-(2,4-dinitro-benzylidene)-N²,N²,N⁴,N⁴-tetramethyl-benzene-1,2,4-triyltriamine 
• 57862-46-1 4-[(E)-(2,4-dinitrobenzylidene)amine]-N,N-dimethylaniline 
• 64-19-7 acetic acid 
• 4836-66-2 2,4-dinitrobenzyl alcohol 
• 108-24-7 acetic anhydride 
• 3013-38-5 2,4-dinitrobenzyl bromide 
• 51361-41-2 2,4-dinitro-benzaldehyde-(N-phenyl oxime ) 
• 1087-09-8 1,4-diphenyl-but-2-yne-1,4-dione 

Downstream Products

• 27402-30-8 5-(2,4-dinitro-benzylidene)-pyrimidine-2,4,6-trione 
• 92163-79-6 4-nitro-2-p-tolylsulfanyl-benzaldehyde 
• 857583-85-8 2-nitro-4-p-tolylsulfanyl-benzaldehyde 
• 153719-44-9 4-(2,4-dinitro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarbonitrile 
• 101410-61-1 2.4-dinitro-trans-cinnamic acid 
• 112768-00-0 (2,4-dinitro-benzylidene)-malonic acid 
• 85818-66-2 2,4-dinitro-cinnamic acid 
• 149742-62-1 N-(2,4-dinitro-benzylidene)-p-toluidine 
• 149742-64-3 4-chloro-N-(2,4-dinitro-benzyliden)-aniline 
• 149742-61-0 N-(2,4-dinitro-benzyliden)-p-anisidine 

Relevant academic research and scientific papers

Highly atom efficient synthesis of 2,2,4,5-tetrasubstituted 3(2H)-furanones having both hydroxyl and amino substituents

We have developed a highly atom efficient synthesis of tetrasubstituted 3(2H)-furanones from easily accessible starting materials such as C,N-diarylaldonitrones and dibenzoylacetylene. Control experiments revealed that reaction of aldonitrones having electron-withdrawing groups on the C-aryl substituent in polar aprotic solvents exhibited high product selectivity while reaction temperature has only a negligible effect on product yield and selectivity.

α-MnO2 modified exfoliated porous g-C3N4 nanosheet (2D) for enhanced photocatalytic oxidation efficiency of aromatic alcohols

Porous graphitic carbon nitride (g-C3N4) was synthesized by taking melamine and ammonium bicarbonate through single-step calcination method followed by ultrasonication to obtain exfoliated porous g-C3N4 (2D) nanosheets. Further enhancement of photocatalytic performance, g-C3N4 nanosheet (2D) was further modified with different weight percentage of (1, 3, 5, and 7) of MnO2. The introduction of α-MnO2 onto the g-C3N4 nanosheet establishes an interlayer channels to promote the migration of charge carriers through the valence band and conduction band of the prepared composite MnO2@g-C3N4. The transformation of photo induced charge carriers adopt the Z-scheme mechanism rather band-transfer mechanism. The accumulated photo generated electrons in conduction band of g-C3N4 is more electro negative than the potential of (O2/O2–.) and able to reduce oxygen to superoxide (O2–.) radical. At the same time, the holes in valence band of α-MnO2 are more electro positive than the potential of (OH–/OH.) and help in oxidate OH– to hydroxyl (OH.) radical. Among all the composites, 3 wt% MnO2 modified g-C3N4 shows the best photocatalytic oxidation efficiency towards all the aromatic alcohols. In presence of visible light, heterojuction formation, and formation of active charged species (OH. and O2–.) were mostly responsible for photocatalytic oxidation of aromatic alcohols through free radical mechanism.

Visible-light mediated facile dithiane deprotection under metal free conditions

Visible light mediated facile and selective dithiane deprotection under metal free conditions is developed. Eosin Y (1 mol%) proved to be an effective catalyst for the dithiane deprotection under the ambient photoredox conditions. The standard household compact fluorescent light source (CFL bulb) proved to be effective under open-air conditions in aqueous acetonitrile at room temperature. The protocol that exhibits a broad substrate scope and functional group tolerance has been shown to expand to a range of transformations for the electron-rich and -deficient thioacetals and thioketals. The synthetic utility of this protocol has also been demonstrated by gram-scale application.

Vicarious Nucleophilic Chloromethylation of Nitroaromatics

Nitroaromatics substituted with electron-acceptor or electron-donor groups undergo vicarious nucleophilic substitution with the lithium salt of dichloromethane to provide chloromethyl-substituted nitroaromatics in good to high yields. The methodology represents a new strategy for the synthesis of benzyl chlorides.

Enantioselective synthesis of diarylcyclopropanecarboaldehydes by organocatalysis

An efficient synthetic method for chiral trisubstituted diarylcyclopropanecarboaldehydes has been developed from substituted benzyl chloride and α,β-unsaturated aldehydes. The reactions were catalyzed by chiral amine catalyst under mild condition to afford the chiral diarylcyclopropanecarboaldehydes in good to high yields and up to excellent enantioselectivities.

Oxidation of 2,4-dinitrotoluene with ozone in the presence of a stop reagent

Liquid-phase oxidation of 2,4-dinitrotoluene with ozone in the presence of acetic anhydride as stop reagent and manganese(II) acetate as catalyst was studied. The major products of oxidation with ozone in acetic anhydride are 2,4-dinitrobenzyl alcohol (65.8%) and 2,4-dinitrobenzaldehyde (18.8%) in the form of the corresponding acetates. A reaction scheme accounting for the results obtained is considered. Pleiades Publishing, Ltd., 2014.

Ozone reaction with 2,4-dinitrotoluene in acetic acid solution

2,4-Dinitrotoluene reacts with ozone along two concurrent pathways: at the aromatic ring yielding stable against ozonolysis hydroperoxide, and at the methyl group with retention of the aromatic structure. The relative amount of products undergoing oxidati

Masked acylation of m-Dinitrobenzene and deriviatives with nitroalkanes under basic conditions: Nitromethylation and α-(hydroxyimino)alkylation

m-Dinitrobenzene and derivatives react with nitromethane or some other primary nitroalkanes in the presence of lithium tert-butoxide in 1,3- dimethyl-2-imidazolizinone (DMI) at room temperature, giving the corresponding 4-nitromethyl and 4-[1-(hydroxyimino)alkyl] derivatives, respectively, in moderate yields. These products are smoothly converted to the corresponding carbonyl compounds by oxidative Nef reaction using ozonized oxygen.

An unexpected linear Bronsted correlation

The reaction of barbiturate and 1,3-dimethylbarbiturate ions with o-, p- and 2,4-dinitrobenzaldehyde was studied. The reactions of barbiturate anion with o- and p-nitrobenzaldehyde exhibit a pH-rate profile different to that the corresponding to the reactions of barbiturate and 1,3-dimethylbarbiturate ions with 2,4-dinitrobenzaldehyde. The dependence of the rate constant on the viscosity of the medium in the pH range 2-4, for all the reactions, indicates the contribution of a diffusion-controlled proton transfer from the hydronium ion to an addition intermediate, T-, in the rate-determining step. Surprisingly, in the reaction of 2,4-dinitrobenzaldehyde with barbiturate and 1,3-dimethylbarbiturate anions, the Bronsted plot for general acid catalysis for carboxylic acids of pKa between 2 to 5 gives a linear relationship with a = 0-707 (r = 0.991), whereas a = 0 is expected, considering the pKa of the addition intermediate T-. On the other hand, the point for the rate constant, considering water as a general acid catalyst, falls approximately 105 times above the corresponding Bronsfed line. The tautomerism existing in the intermediate T- permits these surprising facts to be explained.

An exceptionally simple and convenient method for dethioacetalization

Thioacetals derived from aldehydes and ketones can be unmasked to the corresponding carbonyl compounds in high yield on exposure to a solution of 'oxides of nitrogen' in dichloromethane.