26969-40-4

Basic information

• Product Name: Benzene, nitro-,homopolymer
• Synonyms: Benzene,nitro-, polymers (8CI); Nitrobenzene homopolymer; Poly(nitrobenzene)
• CAS NO: 26969-40-4
• Molecular Formula: C₆H₅NO₂
• Molecular Weight: 123.1094
• Mol File: 26969-40-4.mol
• Article Data: 522

Chemical Properties

• Boiling Point: 210.8°Cat760mmHg
• Flash Point: 81.4°C
• Density: 1.215g/cm³
• CAS DataBase Reference: Benzene, nitro-,homopolymer(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, nitro-,homopolymer(26969-40-4)
• EPA Substance Registry System: Benzene, nitro-,homopolymer(26969-40-4)

Safety Data

• Hazardous Substances Data: 26969-40-4(Hazardous Substances Data)

Usage

General Description

Benzene, nitro-, homopolymer is a type of plastic that is made from the polymerization of nitrobenzene monomers. It is a high molecular weight polymer that is typically used in the production of industrial and commercial plastic products such as pipes, containers, and packaging materials. It is known for its excellent chemical and thermal resistance, as well as its high tensile strength and impact resistance. It is a versatile material that is often used in applications where high-performance and durability are required. However, it is important to handle and dispose of benzene, nitro-, homopolymer carefully, as it can release toxic fumes and pose health hazards if not properly managed.

Upstream product

• 100-05-0 4-nitrobenzenediazonium chloride 
• 127-09-3 sodium acetate 
• 64-18-6 formic acid 
• 64-19-7 acetic acid 
• 88-73-3 2-Chloronitrobenzene 
• 88-74-4 2-nitro-aniline 
• 79-21-0 peracetic acid 
• 62-53-3 aniline 
• 93-59-4 Perbenzoic acid 
• 128-37-0 2,6-di-tert-butyl-4-methyl-phenol 
• 110-86-1 pyridine 
• 100-16-3 4-nitrophenylhydrazone 
• 619-31-8 N,N-dimethyl-3-nitroaniline 
• 98-95-3 nitrobenzene radical anion 

Downstream Products

• 681463-35-4 2-(2,4-dinitro-styryl)-anthraquinone 
• 855289-58-6 4,10-dibenzoyl-benzo[ghi]perylene-1,2-dicarboxylic acid-anhydride 
• 418770-38-4 6-methyl-3,4-diphenyl-phthalic acid-anhydride 
• 860595-98-8 2-(4-methoxy-2,6-dimethyl-[1]naphthoyl)-benzoic acid 
• 185812-83-3 N,N'-biphenyl-4,4'-diyl-bis-phthalamic acid 
• 873987-30-5 3-[1]naphthyl-2,4-diphenyl-2,3-dihydro-benzo[h]quinazolin-2-ol 
• 1016-94-0 2-methylphenazine 
• 26730-04-1 3-methylphenazin-5-oxide 
• 18450-16-3 phenazine-2-carboxylic acid 
• 26730-09-6 10-oxy-phenazine-2-carboxylic acid 
• 86399-73-7 N,O-bis-(4-methoxy-benzoyl)-N-phenyl-hydroxylamine 
• 7465-88-5 4-methoxy-N-phenylbenzamide 
• 17386-89-9 4-Butyroylpyrocatechol 
• 2876-29-1 2-Methoxy-phenazin-10-oxid 

Relevant articles and documents

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EVIDENCE FOR A NON-CHAIN SRN1 REACTION OCCURRING ON A NITROARYLHALIDE

While nitroarylhalides are unreactive in SRN1 reactions, o-iodonitrobenzene (1) gives an efficient nucleophilic substitution with pinacolone enolate ion under photostimulation in liquid ammonia.The observed reactivity of (1) confirms the high rate of fragmentation of the C-I bond of this substrate, as determined in the literature by electrochemical measurements.The origin of such reactivity is traced to the steric inhibition of conjugation of the nitro group with the aromatic ring, as due to the presence of the bulky iodine atom in the ortho position.

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Sub-15 nm CeO2 nanowires as an efficient non-noble metal catalyst in the room-temperature oxidation of aniline

We described herein the facile synthesis of sub-15 nm CeO2 nanowires based on a hydrothermal method without the use of any capping/stabilizing agent, in which an oriented attachment mechanism took place during the CeO2 nanowire formation. The synthesis of sub-15 nm CeO2 nanowires could be achieved on relatively large scales (～2.6 grams of nanowires per batch), in high yields (>94%), and at low cost. To date, there are only a limited number of successful attempts towards the synthesis of CeO2 nanowires with such small diameters, and the reported protocols are typically limited to low amounts. The nanowires displayed uniform shapes and sizes, high surface areas, an increased number of oxygen defects sites, and a high proportion of Ce3+/Ce4+ surface species. These features make them promising candidates for oxidation reactions. To this end, we employed the selective oxidation of aniline as a model transformation. The sub-15 nm CeO2 nanowires catalyzed the selective synthesis of nitrosobenzene (up to 98% selectivity) from aniline at room temperature using H2O2 as the oxidant. The effect of solvent and temperature during the catalytic reaction was investigated. We found that such parameters played an important role in the control of the selectivity. The improved catalytic activities observed for the sub-15 nm nanowires could be explained by: i) the uniform morphology with a typical dimension of 11 ± 2 nm in width, which provides higher specific surface areas relative to those of conventional catalysts; ii) the significant concentration of oxygen vacancies and high proportion of Ce3+/Ce4+ species at the surface that represent highly active sites towards oxidation reactions; iii) the crystal growth along the (110) highly catalytically active crystallographic directions, and iv) the mesoporous surface which is easily accessible by liquid substrates. The results reported herein demonstrated high activities under ambient conditions, provided novel insights into selectivities, and may inspire novel metal oxide-based catalysts with desired performances.

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Novel atom-economic nitration of benzene with a nitrogen dioxide-oxygen system using cocatalyst of solid oxides and lanthanide(III) metal triflates

Benzene is nitrated by a novel atom-economic nitration procedure with a NO2-O2 system in the presence of a mixture of solid oxides and Ln(OTf)3. The only by-product in this novel method is water. The efficiency of NO2 is much high than 50%, the theoretica

Anatase TiO2 mesocrystals enclosed by (001) and (101) facets: Synergistic effects between Ti3+ and facets for their photocatalytic performance

Let's facet it: TiO2 mesocrystals (MCs; see figure) enclosed by (101) and (001) facets can be synthesized by a facile green approach and the ratio of (101)/(001) can be tuned simply by adjusting the solvothermal periods. The photocatalytic activity of TiO2 MCs exposing high proportions of (101) facets possess higher photocatalytic activity than those with lower facets; this can be attributed to the synergistic effect of Ti3+ and the (101)/(001) facet ratio. Copyright

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Changed reactivity of the 1-bromo-4-nitrobenzene radical anion in a room temperature ionic liquid

Radical anions of 1-bromo-4-nitrobenzene (p-BrC6H 4NO2) are shown to be reactive in the room temperature ionic liquid N-butyl-N-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide, ([C4mPyrr][NTf2]), by means of voltammetric measurements. In particular, they are shown to react via a DISP type mechanism such that the electrolysis of p-BrC6H4NO2 occurs consuming between one and two electrons per reactant molecule, leading to the formation of the nitrobenzene radical anion and bromide ions. This behaviour is a stark contrast to that in conventional non-aqueous solvents such as acetonitrile, dimethyl sulfoxide or N,N-dimethylformamide, which suggests that the ionic solvent promotes the reactivity of the radical anion, probably via stabilisation of the charged products.

Mixed lanthanide succinate-sulfate 3D MOFs: Catalysts in nitroaromatic reduction reactions and emitting materials

The first series of mixed succinate/sulfate/Ln MOFs, [Ln2(C 2H4C2O4)2(SO 4)(H2O)2] (RPF-16), where Ln = La, Pr, Nd, and Sm, were hydrothermally obtained and their structures determined by X-ray single crystal diffraction. The crystalline products are a series of isostructural 3D polymeric compounds that crystallise in the monoclinic space group P2(1)/n. Their framework comprises infinite crossing chains of LnO9 sharing edges polyhedra, kept together by succinate and sulfate anions. Topological simplification gives rise to a 3D uninodal six connected net of type pcu alpha-Po primitive cubic. These well-defined compounds show high chemoselectivity towards reduction of the nitro group and present bifunctional activity for the one-pot reductive amination of heptanal at near-complete conversion of the substrates. A general overview of the room-temperature luminescence behavior in the new RPF-16 Ln materials is also reported. The Royal Society of Chemistry 2011.

Strong Environmental Effects upon ΔG0 of Electron Transfer between an Anion Radical and Its Perdeuteriated Analogue

The free energy change for electron transfer from the anion radical of nitrobenzene to perdeuteriated nitrobenzene (PhNO2.- + PhNO2-d5 = PhNO2 + PhNO2-d5.-) has been determined via solution-phase EPR measurements and physical separation of the neutral nitrobenzenes from the solid anion-radical salts.This free energy is largest in hexamethyl-phosphoramide (Γ0 = 1400 J/mol) where the anion radical exists free of ion association and hydrogen bonding.In liquid ammonia, where the anion radicals are strongly hydrogen bonded through the NO2 group, this free energy is only 389 J/mol.The addition of extra sodium cations to the ammonia solution results in a further decrease in ΔG0 to 243 J/mol where it is of the same magnitude as in the solid-state anion radical where the interaction between the cation and anion radical is very strong.Ion association and hydrogen bonding pull spin and charge density into the NO2 group and away from the phenyl ring where isotopic substitution takes place, resulting in a smaller equilibrium isotope effect.In HMPA the isotope effect is even larger than in the gas phase due to stronger solvation of the phenyl moiety than of the NO2 group in this solvent.

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Chain processes in the reduction of aromatic nitroso compounds by triphenylphosphine in the presence of oxygen

The reduction of aromatic nitroso compounds by triphenylphosphine in the presence of oxygen is accompanied by the chain reaction proceeding due to the interaction of trans-isomers of nitroso oxides formed in this system with triphenylphosphine followed by the regeneration of the initial nitrosobenzene.

Oxidation of Primary Aromatic Amines to Nitro Derivatives catalysed by Iron(III) and Manganese(III) Tetraaryl Porphyrins

The oxidation of primary aromatic amines to the corresponding nitro derivatives has been observed in catalytic systems (turnovers/hour up to 18000) containing tert-butyl hydroperoxide and metallo-tetraaryl porphyrins (metal = FeIII or MnII

Enhanced reactivity of silver- and gold-catalysed hydrogenations using silver(I) salts

A novel application of silver(I) salt promoters in silver- and gold-catalysed hydrogenations was applied to the chemoselective reduction of halonitrobenzenes resulting in excellent conversions and selectivities. This reactivity, coupled with the low cost of silver relative to more expensive precious metal counterparts, demonstrates this catalytic system as an attractive alternative for challenging chemoselective transformations.

Mechanism of Cu/Pd-catalyzed decarboxylative cross-couplings: A DFT investigation

The reaction mechanism of decarboxylative cross-couplings of benzoates with aryl halides to give biaryls, which is cooperatively catalyzed by copper/palladium systems, was investigated with DFT methods. The geometries and energies of all starting materials, products, intermediates, and transition states of the catalytic cycle were calculated for the two model reactions of potassium 2- and 4-fluorobenzoate with bromobenzene in the presence of a catalyst system consisting of copper(I)/1,10-phenanthroline and the anionic monophosphine palladium complex [Pd(PMe3)Br]-. Several neutral and anionic pathways were compared, and a reasonable catalytic cycle was identified. The key finding is that the transmetalation has a comparably high barrier as the decarboxylation, which was previously believed to be solely rate-determining. The electronic activation energy of the transmetalation is rather reasonable, but the free energy loss in the initial Cu/Pd adduct formation is high. These results suggested that research aimed at further improving the catalyst should target potentially bridging bidentate ligands likely to assist in the formation of bimetallic intermediates. Experimental studies confirm this somewhat counterintuitive prediction. With a bidentate, potentially bridging ligand, designed to support the formation of bimetallic adducts, the reaction temperature for decarboxylative couplings was reduced by 70 °C to only 100°C.

H3PW12O40 synergized with MCM-41 for the catalytic nitration of benzene with NO2 to nitrobenzene

Developing a new environmentally friendly process for benzene nitration to nitrobenzene has been highly desirable for a long time. In this work, NO2 was used as a nitration agent to replace traditional nitric acid, and different mesoporous SiO2 and their supported heteropoly acid (salt) were employed to catalyze benzene nitration to nitrobenzene. Several typical catalysts were characterized using XRD, BET and FT-IR, and the acid amounts of the various catalysts were determined. The effects of various factors such as different catalysts, the molar ratio of benzene to NO2, reaction temperature, reaction time, HPW loading, the acid amounts of the catalyst and the reuse of the catalyst on the nitration reaction have also been systematically examined. The results indicate that the supported HPW/MCM-41 catalysts exhibit a remarkably synergistic catalytic performance on the nitration reaction of benzene to nitrobenzene. In particular, the 50%HPW/MCM-41 catalyst gives the best results with 73.4% benzene conversion and 98.8% selectivity to nitrobenzene under the optimal reaction conditions. Moreover, the mesoporous structure of MCM-41 was retained under the high loading of HPW. The possible reaction mechanism for the nitration reaction of benzene with NO2 over HPW/MCM-41 is suggested in the present work. This method provides a promising strategy for the preparation of nitro-aromatic compounds from a catalytic nitration reaction by using NO2 as the nitration reagent.

Aromatic nitration with potassium nitrate or nitric acid and boron trifluoride monohydrate

Potassium nitrate/boron trifluoride monohydrate and nitric acid/boron trifluoride monohydrate have been found to be efficient reagents for the nitration of aromatic compounds. Benzene and a series of substituted benzenes were nitrated with excellent yields.

Exploiting a silver-bismuth hybrid material as heterogeneous noble metal catalyst for decarboxylations and decarboxylative deuterations of carboxylic acids under batch and continuous flow conditions

Herein, we report novel catalytic methodologies for protodecarboxylations and decarboxylative deuterations of carboxylic acids utilizing a silver-containing hybrid material as a heterogeneous noble metal catalyst. After an initial batch method development, a chemically intensified continuous flow process was established in a simple packed-bed system which enabled gram-scale protodecarboxlyations without detectable structural degradation of the catalyst. The scope and applicability of the batch and flow processes were demonstrated through decarboxylations of a diverse set of aromatic carboxylic acids. Catalytic decarboxylative deuterations were achieved on the basis of the reaction conditions developed for the protodecarboxylations using D2O as a readily available deuterium source.

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.

Alternative method for the synthesis of triazenes from aryl diazonium salts

An alternative mild method for access to 1-aryl-3,3-dimethyl alkyl triazenes is described. This protocol employs the dropwise addition of a methanolic solution of a carboxylate (RCO2M) or carbonate (CO32?) to a gently heated DMF solution containing an aryl diazonium salt (ArN2+), that had been previously isolated. Presumably homolysis of the weak N–O bond of diazo ether adducts formed in this operation initiates radical pathways that lead to the generation of triazene product. DMF serves as not only a one-electron donor to the diazonium salts employed in this process, but also as a source of dimethylamine radicals that act as a nucleophilic coupling partner. The reaction provides modest yields (ca. 20–40%) across an array of aryl diazonium salts that contain various substitution. Furthermore this unique approach to triazenes contrasts with traditional methods that employ dimethyl amine in reagent form which directly couples with diazonium salts. Seemingly, only one other example employing somewhat similar reaction conditions to this current investigation en route to triazenes has been reported, albeit with lower yields and for one representative example furnished as a side-product. The current work here improves upon the efficiency of this reported result, and further expands the reaction scope.