1145-73-9

Usage

Health Hazard

4-dimethylaminostilbene (XIV), results in widening the target tissue spectrum; XIV induces tumors in the liver, mammary gland, and ear duct. Mice are much more resistant than rats to the carcinogenic activity of both amino-azo dyes and aminostilbenes.

Safety Profile

Poison by ingestion and intraperitoneal routes. Questionable carcinogen with experimental carcinogenic and tumorigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx

Upstream product

• 31233-60-0 1-[4-(dimethylamino)phenyl]-2-phenylethanol 
• 100-42-5 styrene 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 50-00-0 formaldehyd 
• 1694-20-8 4-nitrostilbene 
• 698-70-4 4-Iodo-N,N-dimethylaniline 
• 1197-19-9 4-cyano-N,N-dimethylaniline 
• 1080-32-6 O,O-diethyl benzylphosphonate 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 32264-24-7 diethyl 4-N,N-dimethylaminobenzylphosphonate 
• 100-52-7 benzaldehyde 
• 1552-96-1 4-dimethylaminocinnamic acid 
• 98-80-6 phenylboronic acid 
• 1449-46-3 benzyltriphenylphosphonium bromide 

Downstream Products

• 690258-88-9 cis-[(2,2':6',2''-terpyridine)OsCl2(η2-(C,N)-PhCH=N=CH[C6H4NMe2])]PF6 
• 645-49-8 cis-stilben 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 1383376-85-9 C₃₂H₃₄N₂O 
• 98111-88-7 trimethyl-(stilbenyl-⁽⁴⁾)-ammonium iodide 

Relevant academic research and scientific papers

Palladium supported aminobenzamide modified silica coated superparamagnetic iron oxide as an applicable nanocatalyst for Heck cross-coupling reaction

An applicable palladium-based nanocatalyst was constructed through the immobilization of palladium onto 2-aminobenzamide functionalized silica coated superparamagnetic iron oxide magnetic nanoparticles. The nanocatalyst (named as Pd@ABA@SPIONs@SiO2) was characterized by several characterization methods, including scanning electron microscope (SEM), transmission electron microscopy (TEM), vibrating-sample magnetometry (VSM), energy-dispersive X-ray spectroscopy (EDS), dynamic light scattering (DLS), X-ray powder diffraction (XRD), Fourier transform infrared spectroscopy (FT-IR), inductively coupled plasma (ICP), and X-ray photoelectron spectroscopy (XPS) analyses. Microscopy results showed that the nanoparticles are spherical in shape with 20–25 nm size. The size of the nanoparticles was confirmed by the DLS method. The superparamagnetic nature of the catalyst was confirmed by the VSM method. The successful functionalization of SPIONs@SiO2 was confirmed by FT-IR spectroscopy. The presence of palladium in the structure of the nanocatalyst was illustrated by XRD and EDS analysis. Also using XPS technique, the oxidation state of palladium in Pd@ABA@SPIONs@SiO2 was determined zero before and after the catalyst was applied in Mizoroki-Heck reaction. Several aryl halides and alkenes were reacted in the presence of the nanocatalyst and formed the corresponding products in high isolated yields. The nanocatalyst showed very good reusability and did not decrease its activity after 10 sequential runs. Density functional theory (DFT) calculation was performed to provide a mechanism for the reaction and confirmed the role of the palladium catalyst in the reaction function.

Reductive Difunctionalization of Aryl Alkenes with Sodium Metal and Reduction-Resistant Alkoxy-Substituted Electrophiles

A general method for alkali-metal-promoted reductive difunctionalization of alkenes has been developed by means of reduction-resistant alkoxy-substituted electrophiles. A series of 1,2-diboration and 1,2-dicarbofunctionalization products can be synthesize

Expedient Synthesis of N-Methyl- and N-Alkylamines by Reductive Amination using Reusable Cobalt Oxide Nanoparticles

N-Methyl- and N-alkylamines represent important fine and bulk chemicals that are extensively used in both academic research and industrial production. Notably, these structural motifs are found in a large number of life-science molecules and play vital roles in regulating their activities. Therefore, the development of convenient and cost-effective methods for the synthesis and functionalization of amines by using earth-abundant metal-based catalysts is of scientific interest. In this regard, herein we report an expedient reductive amination process for the selective synthesis of N-methylated and N-alkylated amines by using nitrogen-doped, graphene-activated nanoscale Co3O4-based catalysts. Starting from inexpensive and easily accessible nitroarenes or amines and aqueous formaldehyde or aldehydes in the presence of formic acid, this cost-efficient reductive amination protocol allows the synthesis of various N-methyl- and N-alkylamines, amino acid derivatives, and existing drug molecules.

Unlocking Mizoroki–Heck-Type Reactions of Aryl Cyanides Using Transfer Hydrocyanation as a Turnover-Enabling Step

A new transfer hydrofunctionalization strategy to turnover H-MII-X complexes has enabled both intra- and intermolecular Mizoroki–Heck (MH)-type reactions of aryl cyanides that are challenging to realize under traditional, basic conditions. Initially, a cascade carbonickelation/MH reaction of 2-cyanostyrenes was achieved using a key alkyne transfer hydrocyanation step. Mechanistic experiments supported the proposed catalytic cycle, including the turnover-enabling transfer hydrocyanation step. The reactivity was then extended to the intermolecular MH reaction of benzonitriles and styrenes.

N,N′-Mono substituted acyclic thioureas: Efficient ligands for the palladium catalyzed Heck reaction of deactivated aryl bromides

A series of N,N′-mono substituted acyclic thiourea ligands are found to be highly active phosphine-free catalysts for palladium catalyzed Heck reaction of aryl iodides and bromides with olefins. We have achieved high turnover numbers for aryl iodides with olefins (TONs up to 970,000 for the reaction of iodobenzene with styrene).

Kinetics and mechanism of Horner-Wadsworth-Emmons reaction of weakly acidic phosphonate in solid-liquid phase-transfer catalysis system

Homer-Wadsworth-Emmons (HWE) reaction of diethyl benzylphosphonate (DEBP, pKa = 27.55) with aldehyde was performed in a solid-liquid phase-transfer catalysis (SL-PTC) system using sodium hydroxide as the solid phase. Various parameters that influenced the pseudo-first-order rate constant including stirring speed, catalysts, salt, water and temperature were investigated to explore the process of the generation and transfer of the active intermediate. A reasonable interfacial mechanism of the PTC reaction of the weakly acidic substrate was proved for the first time. HWE reactions under SL-PTC conditions showed high activity and geometric selectivity. It is anticipated that this simple and controllable synthesis method should provide a new idea for HWE reaction in chemical industry.

Substituent effect on the UV spectra of p-disubstituted compounds XPh(CH=CHPh)nY (n=0, 1, 2)

Three parameters, θCCex, θ CCex(XY) and Vmax,parent, are developed to express the substituent effect and the effect of the parent molecular structure of p-disubstituted compounds XPh(CH=CHPh)nY (n=0, 1, 2). The investigated result shows a good correlation between the UV absorption wavenumbers (Vmax) and the three parameters for a diverse set of title compounds, and the correlation equation can be used to predict the UV absorption energy of compounds with the mentioned structure. This approach provides a new insight for the quantitative structure-property relationship (QSPR) correlation of the UV absorption energy of p-disubstituted homologues. Copyright

Amino-salicylaldimine-palladium(II) complexes: New and efficient catalysts for Suzuki and Heck reactions

A series of amino-salicylaldimine-palladium(II) complexes bearing 5-methyl-3-(R-1-ylmethyl)-salicylaldimine ligands (R = morpholine, piperidine, pyrrolidine, 4-methylpiperazin, diisopropylamine) have been prepared and characterized by IR, 1H NMR and elemental analysis. Crystal structure details of complex 2b have been confirmed by X-ray structure analysis. The obtained Pd(II) complexes were found to be effective catalysts for the Suzuki and Heck cross-coupling reactions which could be carried out in the undried solvent under air.

Synthesis of substituted stilbenes via direct decarboxylative coupling of cinnamic acids with arylboronic acids-under palladium catalysis

Readily available cinnamic acids possessing a hydroxy group including ferulic acid efficiently undergo direct decarboxylative arylation under palladium catalysis to form hydroxylated stilbenes. The reaction of related acids is also described.

Lithium hydroxide as base in the Wittig reaction. A simple method for olefin synthesis

A mild and practical procedure for the Wittig olefination, promoted by lithium hydroxide and triphenylbenzyl phosphonium bromide, has been set up for the synthesis of stilbenes and styrenes. The experimental conditions allow aromatic, heteroaromatic, unsaturated and saturated aliphatic aldehydes to give final products in good yields.