7461-51-0

Usage

Uses

Used in Explosive Manufacturing:
2,4,6-Trinitrobenzoinoic acid anylide is used as a key component in the production of explosives and propellants for various applications, such as military, mining, and construction industries. Its high reactivity and sensitivity to heat, friction, and impact make it an effective ingredient in these formulations.
Used in Propellant Production:
In the propellant industry, 2,4,6-Trinitrobenzoinoic acid anylide is used as a critical ingredient to enhance the performance of propellants. Its explosive properties allow for efficient energy release, making it suitable for use in various propulsion systems.
Safety Precautions:
Due to the hazardous nature of 2,4,6-Trinitrobenzoinoic acid anylide, it is essential to exercise caution and follow proper safety procedures when working with or handling 2,4,6-Trinitrobenzoinoic acid anylide. This includes adhering to strict regulations, using appropriate protective equipment, and ensuring the safety of personnel and facilities to prevent accidents and potential harm.

InChI:InChI=1/C13H9N3O5/c17-13(14-10-4-2-1-3-5-10)9-6-11(15(18)19)8-12(7-9)16(20)21/h1-8H,(H,14,17)

Upstream product

• 42444-51-9 3,5-dinitrobenzoyl azide 
• 62-53-3 aniline 
• 99-33-2 3,5-dinitrobenoyl chloride 
• 105673-76-5 3,5-Dinitro-N-phenyl-benzimidic acid 4-nitro-phenyl ester 
• 65-85-0 benzoic acid 
• 99-34-3 3,5-dinitrobenzoic acid 
• 6244-76-4 3,5-Dinitro-N-phenyl-thiobenzamide 
• 29955-47-3 3,5-Dinitro-N-phenyl-benzimidoyl chloride 

Downstream Products

• 73454-97-4 3,5-dinitro-N-(2,4-dinitrophenyl)benzamide 

Relevant academic research and scientific papers

A new mechanism for selective recognition of cyanide in organic and aqueous solution

A simple colorimetric and fluorimetric chemosensor 3,5-dinitro-(N-phenyl)benzamide (DNBA), was synthesized for selective determination of cyanide anion in organic and aqueous solutions via novel chemodosimeter approach. The chemosensor DNBA showed a chrom

Design, Synthesis and in Vitro Tumor Cytotoxicity Evaluation of 3,5-Diamino-N-substituted Benzamide Derivatives as Novel GSK-3β Small Molecule Inhibitors

Glycogen synthase kinase-3 (GSK-3) plays an important regulatory role in various signaling pathways; such as PI3 K/AKT, which is closely related to the occurrence and development of tumors. At present, the most reported active GSK-3 inhibitors have the same structure: lactam ring or amide structure. To find out the GSK-3β small molecule inhibitor with novel, safe, efficient and more uncomplicated synthesis method, we analyzed in-depth reported crystal-binding patterns of GSK-3β small molecule inhibitor with GSK-3β protein, and designed and synthesized 17 non-reported 3,5-diamino-N-substituted benzamide compounds. Their structures were confirmed by 1H-NMR, 13C-NMR, and HR-MS. The preliminary screening of tumor cytotoxicity of compounds in vitro was detected by MTT, and their structure–activity relationships were illustrated. The results have shown that 3,5-diamino-N-[3-(trifluoromethyl)phenyl]benzamide (4d) exhibited significant tumor cytotoxicity against human colon cancer cells (HCT-116) with IC50 of 8.3 μm and showed commendable selectivity to GSK-3β. In addition, Compound 4d induced apoptosis to some extent and possessed modest PK properties.

Identification and SAR Evaluation of Hemozoin-Inhibiting Benzamides Active against Plasmodium falciparum

Quinoline antimalarials target hemozoin formation causing a cytotoxic accumulation of ferriprotoporphyrin IX (Fe(III)PPIX). Well-developed SAR models exist for β-hematin inhibition, parasite activity, and cellular mechanisms for this compound class, but no comparably detailed investigations exist for other hemozoin inhibiting chemotypes. Here, benzamide analogues based on previous HTS hits have been purchased or synthesized. Only derivatives containing an electron deficient aromatic ring and capable of adopting flat conformations, optimal for π-π interactions with Fe(III)PPIX, inhibited β-hematin formation. The two most potent analogues showed nanomolar parasite activity, with little CQ cross-resistance, low cytotoxicity, and high in vitro microsomal stability. Selected analogues inhibited hemozoin formation in Plasmodium falciparum causing high levels of free heme. In contrast to quinolines, introduction of amine side chains did not lead to benzamide accumulation in the parasite. These data reveal complex relationships between heme binding, free heme levels, cellular accumulation, and in vitro activity of potential novel antimalarials.

Development of 3,5-dinitrobenzoate-based 5-lipoxygenase inhibitors

Human 5-lipoxygenase (5-LOX) is a well-validated target for anti-inflammatory therapy. Development of novel 5-LOX inhibitors with higher activities is highly demanded. In previous study, we have built a model for the active conformation of human 5-LOX, and identified naphthalen-1-yl 3,5-dinitrobenzoate (JMC-4) as a 5-LOX inhibitor by virtual screening. In the present work, 3,5-dinitrobenzoate-based 5-lipoxygenase inhibitors were developed. Twenty aryl 3,5-dinitrobenzoates, N-aryl 3,5-dinitrobenzamides and analogues were designed and synthesized. Several of them were found with significantly increased activities according to cell-free assay and human whole blood assay. The structure-activity relationship study may provide useful insights for designing effective 5-LOX inhibitors.

Selective colorimetric sensing of anions in aqueous media through reversible covalent bonding

(Chemical Equation Presented) Selective colorimetric sensing of anions in aqueous media has been studied, which involves reversible covalent bonding as key binding interactions. By introducing a simple nitro chromophore into an o-(carboxamido)trifluoroace

Efficient and convenient deprotection of thiocarbonyl to carbonyl compounds using 3-carboxypyridinium and 2,2′-bipyridinium chlorochromates in solution, dry media, and under microwave irradiation

A synthetic utility of 3-carboxypyridinium (CPCC) and 2,2′- bipyridinium (BPCC) chlorochromates in deprotection reactions is reported. Different types of thioamides, thioureas, thiono esters, and thioketones are deprotected to their corresponding carbonyl compounds with these reagents in good to excellent yields. The reactions were carried out in solution, under solvent-free conditions, and under microwave irradiation. The results show that with both reagents the rates of the reactions and the yields are usually highest under microwave irradiation. Springer-Verlag 2003.

Bismuth(III) nitrate pentahydrate: A convenient and selective reagent for conversion of thiocarbonyls to their carbonyl compounds

A variety of thioamides and thioureas are rapidly transformed to their oxo derivatives with Bi(NO3)3·5H2O in excellent yields. However, thiono esters and thioketones are converted to their corresponding carbonyl compounds in only poor yields. Bi(NO3)3·5H2O is relatively non-toxic, insensitive to air and inexpensive. These features coupled with the selective deprotection of thioamides and thioureas in the presence of thiono esters and thioketones make this method an attractive alternative to the existing routes for deprotection of thiocarbonyl compounds.

Convenient transformation of thiocarbonyl to carbonyl group using benzyltriphenylphosphonium and n-butyltriphenylphosphonium peroxodisulfates

Benzyltriphenylphosphonium and n-butyltriphenylphosphonium peroxodisulfates are stable and easily prepared oxidising agents. These reagents are able to convert different thioamides and thioureas to their oxygen analogues in good to excellent yields. Thiono esters are also transformed to esters in high yields. Thioketones such as thiobenzophenone and thiofluorenone are converted to their ketones in high yields while, 4-nitrothiobenzophenone, 2-aminothiobenzophenone and 4-chlorothiobenzophenone remained intact in the reaction mixture.

A facile and convenient method for deprotection of thiocarbonyls to their carbonyl compounds using oxone under aprotic and nonaqueous conditions

The reaction of oxone as an inexpensive, stable, and commercially available reagent with thiocarbonyl compounds in refluxing acetonitrile has been studied. Primary, secondary, and tertiary thioamides and thioureas are converted to their oxo analogues efficiently. Thiono esters also are transformed to their corresponding esters, while thioketones remained intact under these conditions.

A convenient and inexpensive method for conversion of thiocarbonyl compounds to their oxo derivatives using oxone under solvent-free conditions

A series of thioamides, thioureas and thioesters are transformed to their corresponding carbonyl compounds in good to excellent yields with oxone under solid phase conditions, while thioketones remained unchanged under these conditions.