18264-71-6

Usage

Uses

Used in Explosive and Propellant Production:
2,2'-Dinitrodiphenylamine is used as a stabilizer in the production of explosives, propellants, and rocket fuels. It enhances the safety and performance of these materials by preventing the premature decomposition of the energetic components, thereby ensuring a controlled and efficient release of energy.
Used in Chemical Synthesis:
2,2'-Dinitrodiphenylamine is used as an intermediate in the synthesis of various organic compounds, including dyes and pharmaceuticals. Its unique chemical structure allows for the formation of a wide range of derivatives, making it a versatile building block in the chemical industry.
Used in Research and Development:
Due to its reactivity and potential applications, 2,2'-Dinitrodiphenylamine is also utilized in research and development for the discovery of new compounds and materials with improved properties and performance. Its use in this context contributes to the advancement of various scientific fields, including chemistry, materials science, and pharmaceuticals.

InChI:InChI=1/C12H9N3O4/c16-14(17)11-7-3-1-5-9(11)13-10-6-2-4-8-12(10)15(18)19/h1-8,13H

Upstream product

• 64-17-5 ethanol 
• 64918-56-5 bis-(2-nitro-phenyl)-nitroso-amine 
• 21565-15-1 N-nitroso(2-nitrophenyl)phenylamine 
• 64-19-7 acetic acid 
• 577-19-5 2-nitrophenyl bromide 
• 88-74-4 2-nitro-aniline 
• 609-73-4 o-nitroiodobenzene 
• 88-73-3 2-Chloronitrobenzene 
• 1493-27-2 ortho-nitrofluorobenzene 
• 528-29-0 1,2-Dinitrobenzene 
• 7697-37-2 nitric acid 
• 382165-80-2 N-nitrosodiphenylamine 
• 56-23-5 tetrachloromethane 
• 122-39-4 diphenylamine 

Downstream Products

• 2908-76-1 bis(2,4-dinitrophenyl)amine 
• 92-82-0 Phenazin 
• 613-32-1 5,10-dihydrophenazine 
• 14434-10-7 (2,4-dinitro-phenyl)-(2-nitro-phenyl)-amine 
• 38919-26-5 bis(2-aminophenyl)amine 
• 2055-56-3 2-nitro-2'-aminodiphenylamine 
• 95708-47-7 11H-dibenzo<1,2,5>triazepine-5-oxide 
• 119707-15-2 N-methyl-2-nitro-N-(2-nitrophenyl)aniline 
• 117847-24-2 (4-Nitro-phenyl)-bis-(2-nitro-phenyl)-amine 
• 88-74-4 2-nitro-aniline 
• 1296883-60-7 bis(2-isopropylaminophenyl)amine 
• 1296883-59-4 bis(2-methylaminophenyl)amine 
• 91958-96-2 N-(2-aminophenyl)-N-methylbenzene-1,2-diamine 
• 854254-42-5 bis-(2-acetylamino-phenyl)-amine 

Relevant academic research and scientific papers

Catalytic dioxygen activation by Co(ii) complexes employing a coordinatively versatile ligand scaffold

The ligand bis(2-isobutyrylamidophenyl)amine has been prepared and used to stabilize both mononuclear and dinuclear cobalt(ii) complexes. The nuclearity of the cobalt product is regulated by the deprotonation state of the ligand. Both complexes catalytica

Preparation method of secondary aromatic amine

The invention provides a method for preparing secondary aromatic amine by performing a palladium-catalyzed C-N coupling reaction on (pseudo)aryl halide and (pseudo)heterocyclic aryl halide and primary(heterocyclic)aromatic amine. The method is characterized in that an alkali for promoting the reaction is an alkali metal carboxylate or an alkali metal bicarbonate.

A terphenyl phosphine as a highly efficient ligand for palladium-catalysed amination of aryl halides with 1° anilines

A terphenyl phosphine ligand (2,6-bis(2,4,6-triisopropylphenyl)phenyl-dicyclohexylphosphine, TXPhos) and its supported palladium complex [(TXPhos)(allyl)PdCl] have been developed and the catalyst system is highly efficient in amination of aryl halides with 1° anilines, especially effective for densely functionalized substrates including both partners possessing ortho-ester, acetyl, nitrile and nitro groups. With the TXPhos-supported catalyst system, many partner combinations have been unprecedentedly realized and the base scope has been even extended to KOAc, which is even the best choice in the amination of 2-nitrochlorobenzene.

Round-Trip Oxidative Addition, Ligand Metathesis, and Reductive Elimination in a PIII/PVSynthetic Cycle

A synthetic cycle for aryl C-F substitution comprising oxidative addition, ligand metathesis, and reductive elimination at a Cs-symmetric phosphorus triamide (1, P{N[o-NMe-C6H4]2}) is reported. Reaction of 1 with perfluoroarenes (ArF-F) results in C-F oxidative addition, yielding fluorophosphoranes 1·[F][ArF]. The P-fluoro substituent is exchanged for hydride by treatment with DIBAL-H, generating hydridophosphoranes 1·[H][ArF]. Heating of 1·[H][ArF] regenerates 1 by C-H reductive elimination of ArF-H, where experimental and computational studies establish a concerted but highly asynchronous mechanism. The results provide well-characterized examples of the full triad of elementary mechanistic aryl C-X substitution steps at a single main-group site.

Structure, Spectroscopy, and Reactivity of a Mononuclear Copper Hydroxide Complex in Three Molecular Oxidation States

Structural, spectroscopic, and reactivity studies are presented for an electron transfer series of copper hydroxide complexes supported by a tridentate redox-active ligand. Single crystal X-ray crystallography shows that the mononuclear [CuOH]1+ core is stabilized via intramolecular H-bonds between the H-donors of the ligand and the hydroxide anion when the ligand is in its trianionic form. This complex undergoes two reversible oxidation processes that produce two metastable "high-valent"CuOH species, which can be generated by addition of stoichiometric amounts of 1e- oxidants. These CuOH species are characterized by an array of spectroscopic techniques including UV-vis absorption, electron paramagnetic resonance (EPR), and X-ray absorption spectroscopies (XAS), which together indicate that all redox couples are ligand-localized. The reactivity of the complexes in their higher oxidation states toward substrates with modest O-H bond dissociation energies (e.g., 4-substitued-2,6-di-tert-butylphenols) indicates that these complexes act as 2H+/2e- oxidants, differing from the 1H+/1e- reactivity of well-studied [CuOH]2+ systems.

A Nontrigonal Tricoordinate Phosphorus Ligand Exhibiting Reversible “Nonspectator” L/X-Switching

We report here a “nonspectator” behavior for an unsupported L-function σ3-P ligand (i.e. P{N[o-NMe-C6H4]2}, 1a) in complex with the cyclopentadienyliron dicarbonyl cation (Fp+). Treatment of 1a?Fpsup

Rhodium Complexes Bearing PAlP Pincer Ligands

We report rhodium complexes bearing PAlP pincer ligands with an X-type aluminyl moiety. IR spectroscopy and single-crystal X-ray diffraction analysis of a carbonyl complex exhibit the considerable σ-donating ability of the aluminyl ligand, whose Lewis acidity is confirmed through coordination of pyridine to the aluminum center. The X-type PAlP-Rh complexes catalyze C2-selective monoalkylation of pyridine with alkenes.

P-N Cooperative Borane Activation and Catalytic Hydroboration by a Distorted Phosphorous Triamide Platform

Studies of the stoichiometric and catalytic reactivity of a geometrically constrained phosphorous triamide 1 with pinacolborane (HBpin) are reported. The addition of HBpin to phosphorous triamide 1 results in cleavage of the B-H bond of pinacolborane through addition across the electrophilic phosphorus and nucleophilic N-methylanilide sites in a cooperative fashion. The kinetics of this process of were investigated by NMR spectroscopy, with the determined overall second-order empirical rate law given by ν = -k[1][HBpin], where k = 4.76 × 10-5 M-1 s-1 at 25 °C. The B-H bond activation process produces P-hydrido-1,3,2-diazaphospholene intermediate 2, which exhibits hydridic reactivity capable of reacting with imines to give phosphorous triamide intermediates, as confirmed by independent synthesis. These phosphorous triamide intermediates are typically short lived, evolving with elimination of the N-borylamine product of imine hydroboration with regeneration of the deformed phosphorous triamide 1. The kinetics of this latter process are shown to be first-order, indicative of a unimolecular mechanism. Consequently, catalytic hydroboration of a variety of imine substrates can be realized with 1 as the catalyst and HBpin as the terminal reagent. A mechanistic proposal implicating a P-N cooperative mechanism for catalysis that incorporates the various independently verified stoichiometric steps is presented, and a comparison to related phosphorus-based systems is offered.

CuSO4-mediated decarboxylative C-N cross-coupling of aromatic carboxylic acids with amides and anilines

CuSO4-mediated decarboxylative C-N cross-coupling of aromatic carboxylic acid with amide has been developed, leading to N-arylamides in modest to excellent yields. Anilines bearing electron-withdrawing substituents could also couple efficiently

Reversible intermolecular E-H oxidative addition to a geometrically deformed and structurally dynamic phosphorous triamide

The synthesis and reactivity of geometrically constrained tricoordinate phosphorus (σ3-P) compounds supported by tridentate triamide chelates (N[o-NR-C6H4]23-; R = Me or iPr) are reported.