4103-30-4

Basic information

• Product Name: Diazene, bis(3-nitrophenyl)-
• CAS NO: 4103-30-4
• Molecular Formula: C12H8N4O4
• Molecular Weight: 272.22
• Mol File: 4103-30-4.mol

Chemical Properties

• CAS DataBase Reference: Diazene, bis(3-nitrophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Diazene, bis(3-nitrophenyl)-(4103-30-4)
• EPA Substance Registry System: Diazene, bis(3-nitrophenyl)-(4103-30-4)

Safety Data

• Hazardous Substances Data: 4103-30-4(Hazardous Substances Data)

Upstream product

• 861298-60-4 N,N-dichloro-3-nitro-aniline 
• 141-52-6 sodium ethanolate 
• 1230-85-9 3,3'-dinitro azoxybenzene 
• 75-36-5 acetyl chloride 
• 99-09-2 3-nitro-aniline 
• 586-36-7 3-nitrophenyldiazonium tetrafluoroborate 
• 99-65-0 meta-dinitrobenzene 
• 1516-59-2 3-nitrophenyl azide 
• 53847-35-1 N-benzhydrylidene-3-nitro-aniline 
• 109-89-7 diethylamine 
• 108-88-3 toluene 
• 24586-65-0 mercury(II) acetamide 
• 71-43-2 benzene 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 1230-85-9 3,3'-dinitro azoxybenzene 
• 108-45-2 m-phenylenediamine 
• 1595026-20-2 2-(4-methylphenylsulfonamido)-5,5'-dinitroazobenzene 
• 318515-01-4 (E)-1,2-bis(3-nitrophenyl)diazene 

Relevant articles and documents

Oxidation of aromatic anils in aniline moiety by meta-chloroperbenzoic acid in aqueous acitic medium

The kinetics of oxidation of aromatic anils in aniline moiety by meta-chloroperbenzoic acid (m-CPBA) has been studied in aqueous acitic medium. The order of reaction was found to be second order with respect to aromatic anil and first order with respect to m-chloroperbenzoic acid. The increase of [H+] in this oxidation retards the rate of reaction. The effects of substituents on the oxidation rate were studied with 3 meta- and 5 para-substituted anils at five different temperatures. Thermodynamic parameters for the oxidation have been determined and discussed. meta-Chloroperbenzoic acid oxidation with substituted anils fulfills the isokinetic relationship and Exner relationship but not to any of the linear free energy relationships. The deviation of Hammett plot was noted and a concave downward curve was obtained for the anils with substituents in aniline moiety.

Gold-catalyzed direct hydrogenative coupling of nitroarenes to synthesize aromatic azo compounds

The azo linkage is a prominent chemical motif which has found numerous applications in materials science, pharmaceuticals, and agrochemicals. Described herein is a sustainable heterogeneous-gold-catalyzed synthesis of azo arenes. Available nitroarenes are deoxygenated and linked selectively by the formation of N-N bonds using molecular H2 without any external additives. As a result of a unique and remarkable synergy between the metal and support, a facile surface-mediated condensation of nitroso and hydroxylamine intermediates is enabled, and the desired transformation proceeds in a highly selective manner under mild reaction conditions. The protocol tolerates a large variety of functional groups and offers a general and versatile method for the environmentally friendly synthesis of symmetric or asymmetric aromatic azo compounds.

Oxidation of aromatic anils by sodium perborate in aqueous acetic Acid Medium

The kinetics of oxidation of 9 meta- and 15 para- substituted aromatic anils by sodium perborate were investigated in aqueous acetic acid medium. The reaction was second order with respect to aromatic anil and first order with respect to the sodium perborate. The increase of [H+] in this oxidation retards the rate of the reaction. The observed rate constant for the substituents were plotted against the Hammett constant, δ and a non-linear concave downward curve was obtained for the anils with substituents in the aniline moiety. The observed break in the log kobs versus δwas attributed to the transition state whereas the non-linear concave upward curve was observed for the substituents in the benzaldehyde moiety and a non-linear concave upward curve was observed for the substituents in the combination of aniline and benzaldehyde moiety. The electron withdrawing substituents fall on one side of the curve, having a negative ρvalue and the electron releasing substituents fall on the other side, with a positive ρvalue and a suitable mechanism was proposed.

Phenyliodine(III) diacetate (PIDA) mediated synthesis of aromatic azo compounds through oxidative dehydrogenative coupling of anilines: Scope and mechanism

An efficient and environmentally benign method has been developed for the synthesis of symmetrical and unsymmetrical aromatic azo compounds through phenyliodine(III) diacetate (PIDA) mediated oxidative dehydrogenative coupling of anilines in high yields.

Schiff base complexes of rare earth metal ions: Synthesis, characterization and catalytic activity for the oxidation of aniline and substituted anilines

Several new lanthanide complexes of Pr(III), Sm(III), Gd(III), Tb(III), Er(III) and Yb(III) with the sodium salt of the Schiff base, 2-[(5-bromo-2-hydroxy-benzylidene)-amino]-5-methyl-pentanoic acid, derived from leucine and 5-bromosalicylaldehyde have been synthesized. These complexes having general formula [Ln(HL)(NO3)2(H2O)] ·NO3 were characterized by elemental analysis, UV-vis., FT-IR, EPR, Mass spectrometry and Thermal analysis. The FT-IR spectral data suggested that the ligand behaves as a tridentate ligand with one nitrogen and two oxygen donor atoms, sequence towards central metal ion. From the analytical data, the stoichiometry of the complexes was found to be 1:1 (metal:ligand). The physico-chemical data suggested eight coordination number for Ln(III) Schiff base complexes. Thermal behaviour (TGA/DTA) and fluorescence nature of the complexes were also studied. The Gd(III) Schiff base complex was found to be an efficient catalyst for the oxidation of aniline and substituted anilines under mild conditions.

Kinetic investigation of oxidation of aromatic anils by potassium peroxymonosulfate in aqueous acidic medium

The kinetics of oxidation of aromatic anils to benzaldehyde and azobenzene by potassium peroxymonosulfate has been studied in aqueous acetic acid medium. The low dielectric constant of the medium facilitates the reactivity. It has been found that the variation in the ionic strength of the reaction has a negligible effect on the rate. Similarly, polymerization was not observed when acrylonitrile was added to the reaction mixture. This observation rules out the formation of any free radical in the reaction. The added Mn(II) increases the rate of the reaction, which indicates the involvement of two-electron transfer. Highly negative ΔS# values indicate a structured transition state. The deviation of the Hammett plot was noted, and a concave downward curve was obtained for the anils with substituents in the aniline moiety. The observed break in the log kobs versus σ is attributed to the transition state whereas the concave upward curve was observed for the substituents in the benzaldehyde moiety and in the combination of aniline and benzaldehyde moieties, and a suitable mechanism was proposed.

Reduction of polyfunctional aromatic nitro compounds using lithium aluminium hydride

Aromatic nitro compounds containing yet another functional group are reduced using lithium aluminium hydride in ether. The reduction of nitrobenzanilides results in preferential reduction of amide functionality while the isomeric N-(nitrophenyl) benzamides results in preferential cleavage of the amide bond. Besides, the reduction of 2,2′-dinitrodiphenyl amine 5a, reduction of (bis-2-nitroanilino) methane 5b, 2,2′ -dinitrodiphenylether 5c, 2-nitrophenyl-2′-nitrophenoxymethane 5d, 1,3-dinitrobenzene 6a, 2-nitrobenzaldoxime 6b, 2-N(2′-nitrophenylmethyl) amino benzoic acid 6c, 2-nitrophenoxymethyl phenyl ketone 6d are carried out. Nitro group is found reluctant towards reduction in some cases whereas in some others it is reduced into different extents. This points to the limitation of the suggested azo test for aromatic nitro compounds.

Reactions of Aromatic Nitrocompounds. LXXII. Anionic σ-Complexes of Nitroarenes in the Azocoupling Reaction

In reaction of KBH4 with m-dinitrobenzene in acetonitrile a mixture of isomeric anionic σ-complexes is formed. The reaction of the latter with phenyldiazonium tetrafluoroborates RC6H4N2+BF4

Reductive carbonylation of aromatic dinitro compounds with a palladium(phenanthroline)2(triflate)2 catalyst and an aromatic carboxylic acid as cocatalyst

Reductive carbonylation of aromatic dinitro compounds to afford valuable dicarbamates proceeds at reasonable rates and with high selectivities under the influence of a Pd(phenanthroline)2(triflate)2 catalyst in combination with an aromatic carboxylic acid as cocatalyst.

Facile regeneration of carbonyl compounds from anils by manganese(III) triacetate - A kinetic study

The kinetics of regeneration of carbonyl compounds from anils of benzaldehyde and benzophenone by MnIII(OAc)3 have been studied at 29 +/- 0.1 deg C in aq. acetic acid (76percent, v/v).The corresponding aldehyde/ketone is formed in about 96percent yield along with nearly 48percent of azobenzene in about 3-4 hr.One mol of anil consumes nearly 2 mol of MnIII(OAc)3 for the reaction.The reaction is less susceptible to the electronic influence of substituents on both benzaldehyde and aniline portions.A mechanism involving addition of MnIII(OAc)3 to C = N in the rate determining step has been envisaged to account for the results.