20884-10-0

Basic information

• Product Name: 3-stilbenecarboxaldehyde
• Synonyms: 3-stilbenecarboxaldehyde
• CAS NO: 20884-10-0
• Molecular Weight: 208.26
• Mol File: 20884-10-0.mol

Chemical Properties

• CAS DataBase Reference: 3-stilbenecarboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3-stilbenecarboxaldehyde(20884-10-0)
• EPA Substance Registry System: 3-stilbenecarboxaldehyde(20884-10-0)

Safety Data

• Hazardous Substances Data: 20884-10-0(Hazardous Substances Data)

Upstream product

• 100-42-5 styrene 
• 20883-40-3 3-formylphenylmercury chloride 
• 3132-99-8 m-bromobenzoic aldehyde 
• 108-86-1 bromobenzene 
• 19955-99-8 3-ethenylbenzaldehyde 
• 587-04-2 m-Chlorobenzaldehyde 

Downstream Products

• 27758-94-7 cis,trans-3-styrylstylbene 

Relevant articles and documents

Organostannoxane-supported Pd(0) nanoparticles as efficient catalysts for Heck-coupling reactions

A new functional organostannoxane cage, SnP, that contains phosphine ligands in its periphery has been structurally utilized as support palladium(0) nanoparticles SnPPd. The latter was shown to catalyze the Heck coupling reactions of wide variety of functionalities efficiently.

Mesoporous Hierarchically Hollow Flower-Like CoAl-LDH@N,S-doped Graphene@Pd Nanoarchitectures for Heck Couplings

Abstract: A smart strategy for the synthesis of hierarchical CoAl-LDH hollow spheres assembled with nitrogen and sulfur co-doped graphene for high holding of palladium nanoparticles (CoAl-LDH@N,S-G@Pd) is reported. This architecture exhibited excellent activity in Heck reactions with TOF as high as 1633?h?1 due to a strong metal–support interaction, good electron transfers and high surface area. Graphic Abstract: [Figure not available: see fulltext.].

Ligand-Free C–C Coupling Reactions Promoted by Hexagonal Boron Nitride-Supported Palladium(II) Catalyst in Water

A micron-scale palladium(II) material has been successfully prepared using Schiff base-modified hexagonal boron nitride as a support and used for the first time as an efficient and recyclable catalyst in organic synthesis. The morphology, composition, metal loading and thermal stability of the catalyst were studied using scanning electron microscopy (SEM), X-ray photoelectron spectroscopy (XPS), X-ray diffraction (XRD), infrared spectroscopy (FT-IR), inductively coupled plasma (ICP) and thermogravimetric (TG) analyses. Then, the micron material was tested in various C–C cross-coupling reactions and exhibited excellent catalytic activities in the Suzuki and Heck reactions. Moreover, the catalyst could be easily recovered by simple filtration and reused at least ten times without significant loss of its catalytic activity. In general, this work demonstrates the possibility of using Schiff-base@hexagonal boron nitride as an efficient support for heterogeneous catalysts. (Figure presented.).

Novel cyclodextrin-modified h-BN@Pd(II) nanomaterial: An efficient and recoverable catalyst for ligand-free C-C cross-coupling reactions in water

An environmentally friendly palladium(II) catalyst supported on cyclodextrin-modified h-BN was successfully prepared. The catalyst was characterized by FT-IR, SEM, TG, XRD and XPS, and the loading level of Pd in h-BN@β-CD@Pd(II) was measured to be 0.088?mmol g?1 by ICP. It exhibits excellent catalytic activity for the Suzuki and Heck reactions in water, and can be easily separated and consecutively reused for at least nine times. In addition, a series of pharmacologically interesting products were successfully synthesized using this catalyst to demonstrate its potential applications in pharmaceutical industries. Above all, this work opens up an interesting and attractive avenue for the use of cyclodextrin-functionalized h-BN as an efficient support for hydrophilic heterogeneous catalysts.

Palladium(II)-Schiff base complex immobilized covalently on h-BN: An efficient and recyclable catalyst for aqueous organic transformations

A moisture- and air-stable palladium(II)-Schiff base complex supported on h-BN was simply prepared by using commercially available reagents. This nanomaterial was applied as an excellent and recyclable heterogeneous catalyst for the Suzuki and Heck cross-coupling reactions. And it has been characterized by FT-IR, XRD, SEM, XPS, TG and ICP-AES techniques. High yields, ligand-free, low reaction time, water as solvent, non-toxicity and recyclability of the catalyst are the main merits of these protocols. In addition, a series of pharmacologically relevant products were successfully synthesized using this catalyst. Above all, this work opens up an interesting and attractive avenue for the use of h-BN as an efficient support for heterogeneous catalysts.

C-C bond formation strategy through ecocatalysis: Insights from structural studies and synthetic potential

We report the elaboration of novel bio-sourced ecocatalysts for Heck and Suzuki cross-coupling reactions. Ecocatalysis is based on the recycling of metals issued from phytoremediation or rehabilitation, and an innovative chemical valorization of the subsequent biomass in the field of catalysis. Here, we describe the efficient palladium accumulation by plants (Brassica juncea, Lolium multiflorum) via rhizofiltration. Taking advantage of the remarkable ability of the selected plants to accumulate Pd(II) species into their roots, these latter can be directly used for the preparation of ecocatalysts, called Eco-Pd. The formed Eco-Pd catalysts are thoroughly characterized via ICP-MS, XRD, XPS, TEM, SEM in order to elucidate the chemical composition and morphology of the formed materials. Significant differences to conventional Pd-based catalysts such as palladium(II) chloride can principally be related to a particular Lewis acid behavior of the Eco-Pd catalysts. Finally, the obtained Eco-Pd appear as highly active catalysts in Heck and Suzuki cross-coupling reactions necessitating considerably lower Pd quantity compared to precedently reported bio-sourced palladium containing catalysts.

Ordered mesoporous SBA-15/PrSO3Pd and SBA-15/PrSO3PdNP as active, reusable and selective phosphine-free catalysts in C-X activation Heck coupling process

The incorporation of sulfonate into mesoporous SBA-15 molecular sieves as ligands for palladium ions was used. Then SBA-15/PrSO3Pd and SBA-15/PrSO3PdNP were prepared and applied for the Heck arylation reaction of conjugate alkenes with aryl halides, to afford corresponding cross-coupling products under phosphine-free aerobic conditions with good to excellent yields. These supported palladium pre-catalysts could be separated easily from reaction products and reused several times, showing superiority over homogeneous catalysts for industrial and chemical applications.

Synthesis and catalytic activity of pyrazolyl-functionalized N-heterocyclic carbene palladium complexes

Three pyrazolyl-functionalized N-heterocyclic carbene (NHC) palladium complexes based on 1-[2-(pyrazol-1-yl)phenyl]imidazole have been synthesized and characterized by physico-chemical and spectroscopic methods, and the structures of two of the complexes have been confirmed by single-crystal X-ray diffraction. The pyrazolyl-functionalized NHCs act as chelating N,C-bidentate ligands in these three complexes. Catalytic tests have proved that these complexes exhibit highly effective catalytic activity for the Suzuki-Miyaura and Mizoroki-Heck coupling reactions in water or aqueous/organic media under air. The substituents on the pyrazolyl ring exert different influences on the catalytic activity of the complexes in these coupling reactions.

6H-Dibenzo[d,f-[1,3]diazepin-6-ylidene,5,7-dihydro-5,7-diphenylphosphanyl]: A new ligand for palladium-catalyzed Mizoroki-Heck coupling

A novel and conveniently prepared diphosphine ligand 6H-Dibenzo[d,f-[1,3] diazepin-6-ylidene,5,7-dihydro-5,7-diphenylphosphanyl] (DADPP) combined with [Pd(C3H5)Cl]2 affords an efficient catalytic system for Mizoroki-Heck cross-coupling of aryl halides with alkenes. The system could give the yield of 95% for 4-chloronitrobenzene with 0.05 mol.% [Pd(C 3H5)Cl]2. For the bromide-substituted substrates, the highest turnover number (TON) is up to 96,000,000.

Highly active, selective, and reusable RuO2/SWCNT catalyst for heck olefination of aryl halides

Very fine RuO2 nanoparticles (RuO2NPs) with a mean diameter of about 0.9 nm were decorated on single-walled carbon nanotubes (SWCNTs) by a straightforward "dry synthesis" method. TEM images and the Raman spectrum of the resultant material (RuO2/SWCNT) revealed excellent adhesion and homogeneous dispersion of the RuO2NPs on anchoring sites of the SWCNTs. The surface area of RuO2/SWCNT was found to be 416 m2 g-1. The SEM-EDS results showed that the weight percentage of Ru in RuO2/SWCNT was 13.8%. The oxidation state of Ru in RuO2/SWCNT was +4, as confirmed by XPS and XRD analyses. After the complete characterization, a 0.9 mol % loading of RuO 2/SWCNT was used as a nanocatalyst for the Heck olefination of a wide range of aryl halides to yield products in excellent yields with good turnover numbers and turnover frequencies. Less reactive bromo-and chloroarenes were also used for the formation of coupled products in good yields. RuO 2/SWCNT is regioselective, chemoselective, heterogeneous in nature, and reusable. The stability of RuO2/SWCNT was also studied by means of TEM, ICP-MS, SEM-EDS, and XPS analyses.