1694-20-8

Basic information

• Product Name: 1-NITRO-4-((E)-STYRYL)-BENZENE
• Synonyms: 1-NITRO-4-((E)-STYRYL)-BENZENE;TRANS-4-NITROSTILBENE;(E)-1-Nitro-4-(2-phenylethenyl)benzene;(E)-4-Nitrostilbene;Benzene, 1-nitro-4-(2-phenylethenyl)-, (E)- (9ci);Brn 1311157;Ccris 8463;Nsc 66821
• CAS NO: 1694-20-8
• Molecular Formula: C₁₄H₁₁NO₂
• Molecular Weight: 225.24264
• EINECS: 223-653-5
• Mol File: 1694-20-8.mol
• Article Data: 572

Chemical Properties

• Melting Point: 155.0 to 159.0 °C
• Boiling Point: 366.75°C (rough estimate)
• Flash Point: 153.5°C
• Appearance: /
• Density: 1.1508 (rough estimate)
• Vapor Pressure: 0.000145mmHg at 25°C
• Refractive Index: 1.5780 (estimate)
• CAS DataBase Reference: 1-NITRO-4-((E)-STYRYL)-BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-NITRO-4-((E)-STYRYL)-BENZENE(1694-20-8)
• EPA Substance Registry System: 1-NITRO-4-((E)-STYRYL)-BENZENE(1694-20-8)

Safety Data

• RTECS: WJ6950050
• Hazardous Substances Data: 1694-20-8(Hazardous Substances Data)

Usage

Description

1-NITRO-4-((E)-STYRYL)-BENZENE, also known as a stilbenoid, is a chemical compound with a structure of (E)-stilbene substituted at one of the C-4 positions by a nitro group. It is characterized by its unique molecular structure and potential applications in various industries.

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 
• 23848-91-1 3c-phenyl-2-(4-nitro-phenyl)-acrylic acid 
• 100-42-5 styrene 
• 636-98-6 p-nitrobenzene iodide 
• 13331-27-6 m-nitrobenzene boronic acid 
• 6624-53-9 (Z)-1-nitro-4-(2-phenylethenyl)-benzene 
• 19372-00-0 1-(trimethylsilyl)-2-phenylethene 
• 456-27-9 4-nitrobenzenediazonium tetrafluoroborate 
• 121986-07-0 p-nitromandelonitrile 
• 1100-88-5 benzyltriphenylphosphonium chloride 

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 
• 26624-20-4 p-nitrostilbene dibromide 
• 834-24-2 4-aminostilbene 
• 412025-81-1 acetic acid-(4',α'-dinitro-bibenzyl-α-yl ester) 
• 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 

Relevant articles and documents

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

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

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

Ready approach to poly(vinyldiphenylphosphine): A novel soluble polymer for conveniently conducting Wittig reactions

The novel poly(vinyldiphenylphosphine) could be easily prepared by using the reactions of the cheap poly(vinyl chloride) with sodium phosphides. Poly(vinyldiphenylphosphine) is soluble in common solvents while its corresponding phosphine oxide is hardly soluble in the solvents. Taking advantage of this different solubility, poly(vinyldiphenylphosphine) could be used as a soluble phosphinopolymer for the Wittig reactions. The reactions could take place efficiently to produce the corresponding olefins while the isolation of the products were simple since the resulted poly(vinyldiphenylphosphine oxide) was not soluble in the solvent and could be easily removed by filtration.

N-Heterocyclic carbene palladium (II)-pyridine (NHC-Pd (II)-Py) complex catalyzed heck reactions

A mild, efficient, and practical catalytic system for the synthesis of highly privileged stilbene pharmacophores is reported. This system uses N-heterocyclic carbene palladium (II) Pyridine (NHC-Pd (II)-Py) complex to catalyze the formation of carbon-carbon bonds between olefin derivatives and various bromide. This simple, gentle and user-friendly method can offer a variety of stilbene products in excellent yields under solvent-free condition. And its scale-up reaction has excellent yield and this system can be applied to industrial fields. The utility of this method is highlighted by its universality and modular synthesis of a series of bioactive molecules or important medical intermediates.

Immobilized Pd on a NHC-functionalized metal-organic FrameworkMIL-101(Cr): An efficient heterogeneous catalyst in the heck and copper-free Sonogashira coupling reactions

A heterogeneous palladium catalyst system based on immobilization of palladium moieties on a N-heterocyclic carbene (NHC) modified metal organic framework (MOF) was developed for the Heck and copper-free Sonogashira coupling reactions. In order to prepare this catalyst system, first, MIL-101(Cr) was functionalized with NHC moieties through a post synthetic modification (PSM) approach, and then Pd metal was stabilized on the prepered MIL-101(Cr)-NHC substrate. This material was characterized using various microscopic and spectroscopic techniques and then was used as an efficient heterogeneous Pd catalyst system in the Heck and copper-free Sonogashira reactions. Results of the heterogeneity tests showed that the Pd-NHC-MIL-101(Cr) catalyst can efficiently catalyzed these coupling reactions heterogeneously and no remarkable changes observed in the morphology and structure of MIL-101(Cr) template during the reaction progress. Also, existence of palladium nanoparticles immobilized on the MOF structure affirmed by the TEM and XPS analysis confirmed the oxidation state of Pd. A variety of alkene and alkyne derivatives were synthesized in good to excellent yields using this heterogeneous Pd catalyst system under normal conditions. More importantly Pd-NHC-MIL-101(Cr) catalyst was simply recovered from the reaction medium without remarkable decreasing in its catalytic activities after five times of reusability. The ICP analysis showed the very low Pd and Cr metals leaching, representing high stability and applicability of this catalyst in Pd coupling reactions.