736-31-2

Basic information

• Product Name: (E)-1,1′-(1,2-ETHENEDIYL)BIS(4-NITROBENZENE)
• Synonyms: Ccris 8546;Einecs 212-002-0;(E)-p,p'-Dinitrostilbene;(E)-4,4'-Dinitrostilbene;Stilbene, 4,4'-dinitro-, (E)-;1,1'-(E)-ethene-1,2-diylbis(4-nitrobenzene);(E)-1,1'-(1,2-Ethenediyl)bis(4-nitrobenzene);1,1'-[(E)-1,2-Ethenediyl]bis(4-nitrobenzene);Benzene, 1,1'-(1E)-1,2-ethenediylbis[4-nitro-;1-nitro-4-[(E)-2-(4-nitrophenyl)ethenyl]benzene
• CAS NO: 736-31-2
• Molecular Formula: C₁₄H₁₀N₂O₄
• Molecular Weight: 270.24
• EINECS: 212-002-0
• Mol File: 736-31-2.mol

Chemical Properties

• Melting Point: 288 °C
• Boiling Point: 394.6°Cat760mmHg
• Flash Point: 182.7°C
• Appearance: /
• Density: 1.376g/cm³
• Refractive Index: 1.6500 (estimate)
• CAS DataBase Reference: (E)-1,1′-(1,2-ETHENEDIYL)BIS(4-NITROBENZENE) (CAS DataBase Reference)
• NIST Chemistry Reference: (E)-1,1′-(1,2-ETHENEDIYL)BIS(4-NITROBENZENE) (736-31-2)
• EPA Substance Registry System: (E)-1,1′-(1,2-ETHENEDIYL)BIS(4-NITROBENZENE) (736-31-2)

Safety Data

• Hazardous Substances Data: 736-31-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(E)-1,1'-(1,2-ETHENEDIYL)BIS(4-NITROBENZENE) is used as an intermediate in the synthesis of various organic compounds and dyes. Its unique structure allows it to be a valuable building block for creating a wide range of chemical products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (E)-1,1'-(1,2-ETHENEDIYL)BIS(4-NITROBENZENE) is used as a key component in the production of certain drugs. Its properties make it suitable for the development of new pharmaceuticals with potential therapeutic applications.
Used in Agrochemical Industry:
(E)-1,1'-(1,2-ETHENEDIYL)BIS(4-NITROBENZENE) also finds application in the agrochemical industry, where it is utilized in the development of pesticides and other agricultural chemicals. Its chemical properties contribute to the effectiveness of these products in protecting crops and enhancing agricultural productivity.
Used in Materials Science:
(E)-1,1'-(1,2-ETHENEDIYL)BIS(4-NITROBENZENE) may have potential applications in the field of materials science, particularly in the development of new functional materials. Its unique properties could be harnessed to create innovative materials with specific characteristics for various applications.
Safety Precautions:
It is important to handle (E)-1,1'-(1,2-ETHENEDIYL)BIS(4-NITROBENZENE) with care, as it is toxic and can cause irritation to the skin, eyes, and respiratory system. Proper safety measures, including the use of personal protective equipment and proper ventilation, should be taken to minimize the risk of exposure.

Upstream product

• 588-59-0 stilbene 
• 619-93-2 (Z)-4,4'-dinitrostilbene 
• 93968-39-9 meso-1,2-dibromo-1,2-di(4-nitrophenyl)-2-ethane 
• 100-14-1 4-nitrobenzyl chloride 
• 78-08-0 Triethoxyvinylsilane 
• 456-27-9 4-nitrobenzenediazonium tetrafluoroborate 
• 7553-56-2 iodine 
• 98-95-3 nitrobenzene 
• 91-22-5 quinoline 
• 6277-62-9 2,3t-bis-(4-nitro-phenyl)-acrylic acid 
• 2767-70-6 (p-nitrobenzyl)triphenylphosphonium bromide 
• 555-16-8 4-nitrobenzaldehdye 
• 1747-50-8 4-methyl-N'-[(4-nitrophenyl)methylidene]benzene-1-sulfonohydrazide 
• 100-11-8 1-bromomethyl-4-nitro-benzene 

Downstream Products

• 619-93-2 (Z)-4,4'-dinitrostilbene 
• 105222-70-6 α,α'-dichloro-4,4'-dinitro-bibenzyl 
• 93968-39-9 meso-1,2-dibromo-1,2-di(4-nitrophenyl)-2-ethane 
• 13190-56-2 4,4'-ethanediyl-bis-cyclohexylamine 
• 7314-06-9 (E)-4,4'-diaminostilbene 
• 7297-52-1 nitroaminostilbene 
• 621-95-4 4,4'-diaminodihydrostilbene 
• 659-22-3 trans-4,4'-dihydroxystilbene 
• 2735-14-0 1,2-bis(4-nitrophenyl)acetylene 
• 47241-75-8 (E)-4,4’-diacetoxystilbene 
• 67557-61-3 4.4'-bis-acetylamino-cis-stilbene 
• 1609430-93-4 (1S,2S)-1,2-bis(4-nitrophenyl)ethane-1,2-diol 
• 1075218-61-9 N-methyl-{4-[2-(4-amino-phenyl)-vinyl]-phenyl}-amine 
• 621-96-5 4,4'-diaminostilbene 

Relevant articles and documents

Valorisation of urban waste to access low-cost heterogeneous palladium catalysts for cross-coupling reactions in biomass-derived γ-valerolactone

Herein we report a simple protocol for the valorisation of a common urban biowaste. The lignocellulosic biomass obtained after the pre-treatment of pine needle urban waste is efficiently transformed into a low-cost support (PiNe) for the immobilization of Pd nanoparticles. The final Pd/PiNe heterogeneous catalyst features a small particle size (4.5 nm) and a metal loading (9.9 wt%) comparable with most commercially available and generally used counterparts. In this contribution, we tested the catalytic efficiency of the Pd/PiNe system in two representative cross-couplings, Heck and Hiyama reactions, and compared the results obtained with commercial Pd/C catalyst. The good reactivity in the biomass-derived solvent (GVL) confirms that the Pd/PiNe heterogeneous catalyst is a valid system that can be integrated into a waste valorization chain within a circular economy approach. In addition, the efficiency of the catalyst has also been extended to perform the challenging consecutive Hiyama-Heck reaction to afford differently substituted (E)-1,2-diarylethenes.

Effect of the Linking Group on the Thermoelectric Properties of Poly(Schiff Base)s and Their Metallopolymers

As polymer-based thermoelectric (TE) materials possess attractive features such as light weight, flexibility, low toxicity and ease of processibility, an increasing number of conducting polymers and their composites with high TE performances have been developed in recent years. Up to date, however, the research focusing on the structure-performance relationship remains rare. In this paper, two series of poly(Schiff base)s with either C=C or C≡C linker and their metallopolymers were synthesized and doped with single-walled carbon nanotubes to evaluate how the linking groups affected the TE properties of the resulting composites. Apart from the effect exerted by the morphology, experimental results suggested that the linkers played a key role in determining the band gaps, preferred molecular conformation and extent of conjugation of the polymers, which became key factors that influenced the TE properties of the resulting materials. Additionally, upon coordination with transition metal ions, the TE properties could be tuned readily.

Single-molecule conductance in a unique cross-conjugated tetra(aminoaryl)ethene

A 1,1,2,2-tetrakis(4-aminophenyl)ethene with three paths of π-conjugation, linear-cis, linear-trans and a cross-conjugation, has been prepared. The molecule is able to bind to gold electrodes forming molecular junctions for single-molecule conductance measurements. Only two regimes of conduction are found experimentally. The modelling of the conductance allows to assign them to through-bond transmission in the linear case, while the cross-conjugated channel is further assisted by through-space transmission, partially alleviating the destructive quantum interference. This journal is

Second-generation aryl isonitrile compounds targeting multidrug-resistant Staphylococcus aureus

Antibiotic resistance remains a major global public health threat that requires sustained discovery of novel antibacterial agents with unexploited scaffolds. Structure-activity relationship of the first-generation aryl isonitrile compounds we synthesized led to an initial lead molecule that informed the synthesis of a second-generation of aryl isonitriles. From this new series of 20 compounds, three analogues inhibited growth of methicillin-resistant Staphylococcus aureus (MRSA) (from 1 to 4 μM) and were safe to human keratinocytes. Compound 19, with an additional isonitrile group exhibited improved activity against MRSA compared to the first-generation lead compound. This compound emerged as a candidate worthy of further investigation and further reinforced the importance of the isonitrile functionality in the compounds’ anti-MRSA activity. In a murine skin wound model, 19 significantly reduced the burden of MRSA, similar to the antibiotic fusidic acid. In summary, 19 was identified as a new lead aryl isonitrile compound effective against MRSA.

Molecular probes for imaging of myelin

A molecular probe for labeling myelin includes a fluorescent trans-stilbene derivative.

From 4-nitrotoluene and 4,4′-dinitrobibenzyl to: E -4,4′-dinitrostilbene: An electrochemical approach

The dianions formed by the electroreduction of Z-O2NC6H4CHCHC6H4NO2, E-O2NC6H4CHCHC6H4NO2, O2NC6H4CH2-CH2C6H4NO2 or O2NC6H4CMeH-CMeHC6H4NO2, as well as the anion radical arising from 4-nitrotoluene, are stable, in the time scale of cyclic voltammetry (DMF + 0.10 M NBu4BF4). However, in the electrolysis time scale (from minutes to hours), only the dianion O2NC6H4CMeH-CMeHC6H4NO22- remains stable, since the reduced species, Z-O2NC6H4CHCHC6H4NO22-, O2NC6H4CH2-CH2C6H4NO22- or O2NC6H4Me-, evolve to form the E-O2NC6H4CHCHC6H4NO22- dianion. This intermediate is recovered as the neutral species E-O2NC6H4CHCHC6H4NO2 with concomitant water reduction after the work-up with water, as demonstrated by combined electrolysis, cyclic voltammetry experiments, UV-spectroelectrochochemistry and theoretical calculations. Bulk electrolysis under optimized conditions (ACN + 0.10 M NBu4BF4) provides 40% and 67% isolated yields of E-4,4′-dinitrostilbene from 4-nitrotoluene and 4,4′-dinitrobibenzyl, respectively.

Method for preparing nitro compound by using graphene to catalyze nitric oxide

The invention discloses a method for preparing a nitro compound by using graphene to catalyze nitric oxide. A graphene oxide carbon material is used for catalysis of a reaction of nitric oxide and a nitrification substrate such as an aromatic compound to prepare the nitro compound. The method is used for replacing a traditional nitric acid/sulfur acid method to prepare the nitro compound, so thatthe atom utilization rate of the reaction is increased, the energy is saved, and the emission is reduced; and the method has the characteristic of atom economy during industrial preparation of the nitro compound.

Oxidative Dephosphorylation of Benzylic Phosphonates with Dioxygen Generating Symmetrical trans-Stilbenes

Under a dioxygen atmosphere, benzylphosphonates and related phosphoryl compounds can readily produce the corresponding trans-stilbenes in high yields with high selectivity upon treatment with bases. Various functional groups were tolerable under the reaction conditions.

In Vitro, In Silico, and In Vivo Analyses of Novel Aromatic Amidines against Trypanosoma cruzi

Five bis-arylimidamides were assayed as anti-Trypanosoma cruzi agents by in vitro, in silico, and in vivo approaches. None were considered to be pan-assay interference compounds. They had a favorable pharmacokinetic landscape and were active against trypomastigotes and intracellular forms, and in combination with benznidazole, they gave no interaction. The most selective agent (28SMB032) tested in vivo led to a 40% reduction in parasitemia (0.1 mg/kg of body weight/5 days intraperitoneally) but without mortality protection. In silico target fishing suggested DNA as the main target, but ultrastructural data did not match.

Thermal rearrangement of 2,3-diaryl-1-phthalimidoaziridines

2,3-Diaryl-1-phthalimidoaziridines and 2,3-diaryl-1-phthalimidoaziridine-2-carbonitriles were found to readily undergo thermal rearrangement into imines via 1,2-migration of the phthalimido group and accompanying C-C bond cleavage. Isomerization proceeds regioselectively with preferable migration to the electron-deficient carbon atom. Interestingly, this reaction was found to predominate even in the presence of dipolarophiles.