497-87-0

Basic information

• Product Name: Diazene, bis(2-fluorophenyl)-, 1-oxide
• CAS NO: 497-87-0
• Molecular Formula: C12H8F2N2O
• Molecular Weight: 234.205
• Mol File: 497-87-0.mol

Chemical Properties

• CAS DataBase Reference: Diazene, bis(2-fluorophenyl)-, 1-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: Diazene, bis(2-fluorophenyl)-, 1-oxide(497-87-0)
• EPA Substance Registry System: Diazene, bis(2-fluorophenyl)-, 1-oxide(497-87-0)

Safety Data

• Hazardous Substances Data: 497-87-0(Hazardous Substances Data)

Upstream product

• 1493-27-2 ortho-nitrofluorobenzene 
• 401-44-5 2,2'-difluoroazobenzene 
• 348-54-9 2-Fluoroaniline 

Downstream Products

• 454-21-7 1,2-bis(2-fluorophenyl)hydrazine 
• 401-44-5 2,2'-difluoroazobenzene 
• 448-97-5 3,3'-difluorobiphenyl-4,4'-diamine 

Relevant articles and documents

The polyhedral nature of selenium-catalysed reactions: Se(iv) species instead of Se(vi) species make the difference in the on water selenium-mediated oxidation of arylamines

Selenium-catalysed oxidations are highly sought after in organic synthesis and biology. Herein, we report our studies on the on water selenium mediated oxidation of anilines. In the presence of diphenyl diselenide or benzeneseleninic acid, anilines react with hydrogen peroxide, providing direct and selective access to nitroarenes. On the other hand, the use of selenium dioxide or sodium selenite leads to azoxyarenes. Careful mechanistic analysis and 77Se NMR studies revealed that only Se(iv) species, such as benzeneperoxyseleninic acid, are the active oxidants involved in the catalytic cycle operating in water and leading to nitroarenes. While other selenium-catalysed oxidations occurring in organic solvents have been recently demonstrated to proceed through Se(vi) key intermediates, the on water oxidation of anilines to nitroarenes does not. These findings shed new light on the multifaceted nature of organoselenium-catalysed transformations and open new directions to exploit selenium-based catalysis.

Selective Oxidation of Anilines to Azobenzenes and Azoxybenzenes by a Molecular Mo Oxide Catalyst

Aromatic azo compounds, which play an important role in pharmaceutical and industrial applications, still face great challenges in synthesis. Herein, we report a molybdenum oxide compound, [N(C4H9)4]2[Mo6O19] (1), catalyzed selective oxidation of anilines with hydrogen peroxide as green oxidant. The oxidation of anilines can be realized in a fully selectively fashion to afford various symmetric/asymmetric azobenzene and azoxybenzene compounds, respectively, by changing additive and solvent, avoiding the use of stoichiometric metal oxidants. Preliminary mechanistic investigations suggest the intermediacy of highly active reactive and elusive Mo imido complexes.

Chemoselective electrochemical reduction of nitroarenes with gaseous ammonia

Valuable aromatic nitrogen compounds can be synthesized by reduction of nitroarenes. Herein, we report electrochemical reduction of nitroarenes by a protocol that uses inert graphite felt as electrodes and ammonia as a reductant. Depending on the cell voltage and the solvent, the protocol can be used to obtain aromatic azoxy, azo, and hydrazo compounds, as well as aniline derivatives with high chemoselectivities. The protocol can be readily scaled up to >10 g with no decrease in yield, demonstrating its potential synthetic utility. A stepwise cathodic reduction pathway was proposed to account for the generations of products in turn.

Palladium Nanoparticles on Silica Nanospheres for Switchable Reductive Coupling of Nitroarenes

Abstract: In this study, we synthesized a robust and sustainable Pd/SiO2 nanospheres catalyst. Further, its catalytic activity was demonstrated for the direct reductive coupling of nitroarenes under mild conditions. While the reaction with Pd nanoparticles on other supporting materials such as modified carbon materials and TiO2, under similar conditions, resulted formation of amines exclusively. Therefore, it was confirmed that the SiO2 was found to be the best supporting material towards the selective reductive coupling of nitroarenes. Also, the catalyst could be recycled up to five cycles with a marginal loss of product yield ( 2% yield). Graphic Abstract: [Figure not available: see fulltext.].

A Green Chemoenzymatic Process for the Synthesis of Azoxybenzenes

An efficient chemoenzymatic process for the synthesis of azoxybenzenes was developed. A peracid was generated in situ by Novozym 435, and then a range of anilines were oxidized by the produced peracid to afford azoxybenzenes in yields ranging from 63.1 to 94.1 %. This method expands the application of lipase in organic synthesis and provides an alternative method for the synthesis of azoxybenzenes.

Selective N-oxidation of aromatic amines to nitroso derivatives using a molybdenum acetylide oxo-peroxo complex as catalyst

The molybdenum acetylide oxo-peroxo complex obtained in situ by the treatment of the corresponding molybdenum acetylide carbonyl complex, CpMo(CO)3(C{triple bond, long}CPh); Cp = η5-C5H5 with H2O2, has been used as an efficient catalyst for selective N-oxidation of primary amines to nitroso derivatives. Excellent amine conversion (up to 100%) and very high selectivity for nitroso compounds (99%) have been obtained using 30% hydrogen peroxide as an oxidant. The oxo peroxo Mo(VI) complex has also been found to be very active for the oxidation of various substituted primary aromatic amines with electron donating as well as electron withdrawing substituents on the aromatic ring.

Anti-androgenic activity of substituted azo- and azoxy-benzene derivatives.

Substituted phenylazo and phenylazoxy compounds were systematically prepared and their anti-androgenic activity was measured in terms of (1) the growth-inhibiting effect on an androgen-dependent cell line, SC-3, and (2) the binding affinity to nuclear androgen receptor. Generally, azo/azoxy compounds showed cell toxicity, and the growth-inhibiting effects on SC-3 cells correlated with the toxicity. However, some compounds, including 4,4'-dinitroazobenzene (25), 4,4'-dimethoxyazobenzene (33), and 2,2'-dichloroazoxybenzene (47), possessed potent anti-androgenic activity without apparent cell toxicity.

Catalytic selective oxidation of amines with hydroperoxides over molecular sieves: Investigations into the reaction of alkylamines, arylamines, allylamines and benzylamines with H2O2 and TBHP over TS-1 and CrS-2 as the new catalyst

The liquid phase oxidation of various substituted amines with dil H2O2 and tert-butyl hydroxyperoxide (TBHP) has been investigated over titanium and chromium silicates respectively. While TS-1/H2O2 combination exhibits a remarkable activity and selectivity in the oxidation of arylamines to produce the symmetrical azoxybenzenes, CrS-2 catalyzes the selective oxidation of various substituted amines to the corresponding nitro compounds by oxidation with 70% TBHP. The nature of the reactive intermediates during the oxidation of anilines to nitrobenzenes has been established using cyclic voltammetry experiments. Further, amines possessing α C-H bonds are selectively oxidized to either oximes or the carbonyl compounds on reaction with H2O2 catalyzed by TS-1.

Selective Catalytic Oxidation of Arylamines to Azoxybenzenes with H2O2 over Zeolites

Catalytic version of the H2O2-TS-1 combination has been shown to display a good reaction selectivity in the liquid-phase oxidation of anilines to symmetrical azoxybenzenes.