73405-61-5

Upstream product

• 119-75-5 2-nitro-N-phenylaniline 
• 73405-59-1 1-(2-nitrophenyl)-1-phenylurea 
• 1493-27-2 ortho-nitrofluorobenzene 
• 1515830-29-1 2-benzylidene-1-(2-nitrophenyl)-1-phenylhydrazine 
• 588-64-7 benzaldehyde phenylhydrazone 

Downstream Products

• 1515830-47-3 3-methyl-1-phenyl-1,4-dihydro-1,2,4-benzotriazin-4-yl 
• 1515830-53-1 1-phenyl-3-trifluoromethyl-1,4-dihydro-benzo[e][1,2,4]triazin-4-yl 
• 1515830-56-4 3-(adamant-1-yl)-1-phenyl-1,4-dihydro-1,2,4-benzotriazin-4-yl 
• 1515829-99-8 N′-(2-nitrophenyl)-N′-phenylacetohydrazide 
• 1515830-05-3 2,2,2-Trifluoro-N′-(2-nitrophenyl)-N′-phenylacetohydrazide 
• 1515830-26-8 N′-(2-nitrophenyl)-N′-phenyl-1-adamantanecarbohydrazide 

Relevant academic research and scientific papers

The suppression of columnar π-stacking in 3-adamantyl-1-phenyl-1,4-dihydrobenzo[e][1,2,4]triazin-4-yl

3-Adamantyl-1-phenyl-1,4-dihydrobenzo[e][1,2,4]triazin-4-yl(4) crystallizes as chains of radicals where the spin bearing benzotriazinyl moieties are isolated from each other. Magnetic susceptibility studies in the 5-300 K temperature region indicate that

Synthesis of reduction-sensitive 1,1-diarylhydrazines from 1,1-diarylamines

1-(2-Nitrophenyl)-1-phenylamine and methyl 4-((2-nitrophenyl)amino)benzoate have been transformed into their corresponding urea derivatives through the action of chlorosulfonyl isocyanate. The initial sulfimidate product from the former reaction has sufficient stability so that it can be isolated and characterized as its disodium salt, and this, as well as three other subsequent products, have been characterized by X-ray diffraction. The corresponding intermediary urea was converted into its hydrazine derivative via a Hofmann rearrangement under oxidative conditions. Density functional theory has been used to examine the nature of the intermediates and transition states for the Hofmann rearrangement. There is little theoretical indication for a cyclic aziridinonium intermediate and the transition state between the urea and the isocyanate corresponds to a reactant-like rotation of the planar singlet nitrene before migration and formation of the new N-N bond.

Route to benzo- and pyrido-fused 1,2,4-triazinyl radicals via N ′-(Het)aryl- N ′-[2-nitro(het)aryl]hydrazides

A two-step route to 1,3-disubstituted benzo- and pyrido-fused 1,2,4-triazinyl radicals is presented. The route involves the N′-(2-nitroarylation) of easily prepared N′-(het)arylhydrazides via nucleophilic aromatic substitution of 1-halo-2-nitroarenes, which in most cases gives N′-(het)aryl-N′-[2-nitro(het)aryl]hydrazides in good yields. Mild reduction of the nitro group followed by an acid-mediated cyclodehydration gives the fused triazines, which upon alkali treatment afford the desired radicals. Fifteen examples of radicals are presented bearing a range of substituents at N-1, C-3, and C-7, including the pyrid-2-yl and 8-aza analogues. This route to the N′-(het)aryl-N′-[2-nitro(het)aryl]hydrazides, which works well with benzo- and picolinohydrazides, required a modification for aceto- and trifluoroacetohydrazides that involved a multistep synthesis of asymmetrically 1,1-diaryl-substituted hydrazines.

A magnetostructural investigation of an abrupt spin transition for 1-phenyl-3-trifluoromethyl-1,4-dihydrobenzo[e][1,2,4]triazin-4-yl

1-Phenyl-3-trifluoromethyl-1,4-dihydrobenzo[e][1,2,4]triazin-4-yl is the first example of a hydrazyl radical that shows a reversible sharp spin transition fully completed within 5(1) K. The nominally first-order transition takes place at ca. 58(2) K and proceeds via subtle changes of intra- and interstack interactions between two similar structural phases. The low-temperature phase (5-60 K) is diamagnetic and has a singlet ground state (2Jexp = -166.8 cm-1, gsolid = 2.0042, ρ = 0.2%) stemming from a multicenter two-electron interaction. The high-temperature phase (60-300 K) is paramagnetic as a result of noninteracting S = 1/2 spins arising from weakly bound dimers.

An efficient synthesis of 1,1-disubstituted hydrazines

1,1-disubstituted hydrazines were prepared from the corresponding 1,1-disubstituted ureas by means of the Hofmann rearrangement reaction. The yields were fairly good, except from the ureas susceptible to oxidation, and thus the present method represents an additional and efficient procedure for the synthesis of 1,1-disubstituted hydrazines.