1694-20-8

Usage

Uses

Used in Chemical Synthesis:
1-NITRO-4-((E)-STYRYL)-BENZENE is used as an intermediate in the synthesis of various organic compounds, particularly those involving the stilbenoid family. Its unique structure allows for further functionalization and modification, making it a valuable building block in the development of new molecules with specific properties and applications.
Used in Pharmaceutical Industry:
1-NITRO-4-((E)-STYRYL)-BENZENE is used as a starting material for the development of new pharmaceutical compounds. Its structural features can be exploited to design and synthesize novel drugs with potential therapeutic applications, such as those targeting specific receptors or enzymes in the treatment of various diseases.
Used in Material Science:
1-NITRO-4-((E)-STYRYL)-BENZENE can be utilized in the development of advanced materials with specific properties, such as optical, electronic, or mechanical characteristics. Its incorporation into polymers or other materials can lead to the creation of novel materials with enhanced performance in various applications, including sensors, displays, or energy storage devices.
Used in Dye and Pigment Industry:
Due to its unique structure and potential for functionalization, 1-NITRO-4-((E)-STYRYL)-BENZENE can be used as a precursor for the synthesis of dyes and pigments with specific color properties. These dyes and pigments can be employed in various industries, such as textiles, plastics, or printing inks, to impart desired color characteristics to the final products.

Hazard

A poison.

Safety Profile

A poison by intraperitoneal route. Mutation data reported. Whenheated to decomposition it emits toxic vapors of NOx.

InChI:InChI=1/C14H11NO2/c16-15(17)14-10-8-13(9-11-14)7-6-12-4-2-1-3-5-12/h1-11H/b7-6+

Upstream product

• 110-89-4 piperidine 
• 99-99-0 1-methyl-4-nitrobenzene 
• 100-52-7 benzaldehyde 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 1694-20-8 4-nitrostilbene 
• 100-42-5 styrene 
• 636-98-6 p-nitrobenzene iodide 
• 13331-27-6 m-nitrobenzene boronic acid 
• 121986-07-0 p-nitromandelonitrile 
• 1100-88-5 benzyltriphenylphosphonium chloride 
• 532-28-5 (RS)-mandelonitrile 
• 1530-42-3 (4-nitrobenzyl)triphenylphosphonium chloride 
• 26624-20-4 p-nitrostilbene dibromide 
• 1923-01-9 trimethyl(1-phenylvinyl)silane 

Downstream Products

• 1694-20-8 4-nitrostilbene 
• 13024-49-2 4-aminodibenzyl 
• 4309-66-4 p-amino-trans-stilbene 
• 100872-28-4 N-nitroso-N-trans-stilben-4-yl-hydroxylamine 
• 15794-97-5 (+/-)-erythro-4,α,α'-tribromo-4'-nitro-bibenzyl 
• 138313-27-6 bis<4-(2-phenylethenyl)phenyl>diazene 
• 5692-67-1 (Z)-di-trans-stilben-4-yl-diazene-N-oxide 
• 4336-57-6 trans-2-(4-nitrophenyl)-3-phenyloxirane 
• 412025-81-1 acetic acid-(4',α'-dinitro-bibenzyl-α-yl ester) 
• 26624-20-4 p-nitrostilbene dibromide 
• 24533-07-1 (1RS,2SR)-1,2-dibromo-1-(4'-nitrophenyl)-2-phenylethane 
• 51039-61-3 1-[3-(4-nitro-phenyl)-4,5-diphenyl-pyrrol-2-yl]-isoquinoline 
• 6624-53-9 (Z)-1-nitro-4-(2-phenylethenyl)-benzene 
• 24533-07-1 erythro-1,2-dibromo-1-(4-nitrophenyl)-2-phenylethane 

Relevant academic research and scientific papers

Cis/trans conversion of potassium derivatives of 2- and 4-nitrostilbenes

Potassium derivatives of 2- and 4-nitrostilbenes exist in non-dissociating solvents as coordination complexes with localization of the metal at the nitro group.Stilbene components of the complexes undergo cis/trans conversion, the extent of which does not

Catalytic applications of 1,2,4-diazaphospholide-based ruthenium complexes in the Heck reaction

The palladium-catalyzed Heck reaction was effected with two ruthenium complexes bearing unique heterocyclic 1,2,4-diazaphospholide ligands that contain sp2-hybridized phosphorus atoms.

A new recyclable Pd catalyst supported on vertically aligned carbon nanotubes for microwaves-assisted Heck reactions

Palladium supported on vertically aligned multi-walled carbon nanotubes (Pd/VA-CNTs) is used as catalyst for the C-C coupling reactions of p-iodonitrobenzene with styrene and ethyl acrylate under microwaves irradiation. Pd/VA-CNTs catalyst exhibits higher

Mild and rational synthesis of palladium complexes comprising C(4)-bound N-heterocyclic carbenes

Oxidative addition of pyridyl-functionalised 4-iodoimidazolium salts to palladium(0) gives catalytically active complexes in which the N-heterocyclic carbene is bound to the palladium(ii) centre in a non-classical bonding mode via C(4). The Royal Society of Chemistry 2006.

Oxazoline Chemistry. Part 11: Syntheses of natural and synthetic isoflavones, stilbenes and related species via C-C bond formation promoted by a Pd-oxazoline complex

The complex trans-[PdCl2(2-ethyl-2-oxazoline- κ1N)2] (1) is shown to be an active and oxidatively robust catalyst for C-C bond forming reactions (Heck, Sonogashira, Ullmann, Miyaura-Suzuki, etc.). These reactions can be carried out in air without rigorous solvent/substrate purification and in the absence of additional free ligand. The general methodology described above has been applied to the high yield and regio-selective formation, via Miyaura-Suzuki coupling, of natural and synthetic isoflavones (i.e., isoflavone, 2′-methylisoflavone [7b], 3′-methylisoflavone [7c] and 3′,4′-benzoisoflavone: [7d]). Compounds 7c and 7d are previously unknown. In addition, the synthesis of (E)-tris-O-methylresveratrol and (E)-3,5-dimethoxystilbene is also described; the former is a recognized anti-cancer agent while the latter is a biologically active extract from the bark of the conifer species Pinus armandii. Both of these latter products are produced as a result of a Heck coupling reaction promoted by 1.

Application of an air stable Pd oxazoline complex for Heck, Suzuki, Sonogashira and related C-C bond-forming reactions

The novel complex trans-[PdCl2(η1-N-2-ethyl-2- oxazoline)2] is shown to be an active and oxidatively robust catalyst for C-C bond-forming reactions (Heck, Sonogashira, Ullman, Suzuki), which can be carried out in air witho

The effects of 4′-alkyl substituents on the mutagenic activity of 4-amino- and 4-nitrostilbenes in Salmonella typhimurium

Six derivatives of trans-4-aminostilbene bearing different alkyl groups in the 4′-position and six of the corresponding nitro compounds were synthesized and tested for their mutagenic potency in Salmonella typhimurium strains TA98 and TA100. Regarding the test series in presence of S9-mix, maximum activity was observed for those trans-4-aminostilbenes and trans-4-nitrostilbenes bearing small alkyl substituents like methyl and ethyl. More bulky substituents reduced the mutagenic potential in the order iso-propyl ethyl > iso-propyl > sec-butyl > tert-butyl). These trends have been compared with quantitative structure activity relationship (QSAR) model predictions, leading to the conclusion that steric demand is an important factor for mutagenicity of substituted aminostilbenes and nitrostilbenes. The unexpected result for the tert-butyl nitrostilbene tested with metabolic activation may be attributed to a different metabolic pathway.

Enhanced Heck reaction on flower-like Co(Mg or Ni)Al layered double hydroxide supported ultrafine PdCo alloy nanocluster catalysts: The promotional effect of Co

A series of PdCo alloy nanocluster (NC) catalysts x-PdCor/Co(Mg or Ni)Al-LDH (x: Pd loading, r: Co/Pd molar ratio) were synthesized by immobilizing ultrafine PdCor-PVP NCs on flower-like layered double hydroxide (LDH) supports. The s

Heterogeneous heck catalysis with palladium-grafted molecular sieves

The synthesis and characterization of palladium-grafted mesoporous MCM- 41 material, designated Pd-TMS11, are described. The material is investigated for carbon-carbon coupling reactions (Heck catalysis) with activated and nonactivated aryl substrates. Fo

Green and sustainable palladium nanomagnetic catalyst stabilized by glucosamine-functionalized Fe3O4@SiO2 nanoparticles for Suzuki and Heck reactions

A novel magnetic and heterogeneous palladium-based catalyst stabilized by glucosamine-functionalized magnetic Fe3O4@SiO2 nanoparticle was synthesized. The strategy relies on the covalently bonding of glucosamine to cyanuric chloride-functionalized magnetic nanoparticles followed by complexation with palladium. The structure of magnetic nanocatalyst was fully determined by FT-IR, XRD, DLS, FE-SEM, TEM, ICP, UV-Vis, TGA, VSM, and EDX. The obtained results confirmed that the palladium nanoparticles stabilized by glucosamine immobilized onto the magnetic support exhibited high activity in cross-coupling reactions of Suzuki-Miyaura and Mizoroki-Heck. Various aryl halides were coupled with arylboronic acid (Suzuki cross-coupling reaction) and olefins (Heck reactions) under the green conditions to provide corresponding products in high to excellent yields. Interestingly, the catalyst can be easily isolated from the reaction media by magnetic decantation and can subsequently be applied for consecutive reaction cycles (at least seven times) with no notable reduction in the catalytic activity.