66-98-8

Usage

Chemical Properties

Yellow crystalline powder

Synthesis Reference(s)

The Journal of Organic Chemistry, 51, p. 2627, 1986 DOI: 10.1021/jo00364a002

Upstream product

• 2403-54-5 2-(4-chlorophenyl)-1,3-dioxolane 
• 106-41-2 4-bromo-phenol 
• 92-52-4 biphenyl 
• 201230-82-2 carbon monoxide 
• 38775-22-3 2,2″-([1,1′-biphenyl]-4,4′-diyldi-2,1-ethenediyl)bis-benzenesulfonic acid 
• 15164-44-0 p-(iodophenyl)carboxaldehyde 
• 591-50-4 iodobenzene 
• 87199-17-5 4-formylphenylboronic acid, 
• 1122-91-4 4-bromo-benzaldehyde 
• 7440-66-6 zinc 
• 857197-21-8 2,4,6-tris(4-formylphenyl)boroxin 
• 2158-59-0 cryptone 
• 104-88-1 4-chlorobenzaldehyde 
• 98-80-6 phenylboronic acid 

Downstream Products

• 79567-15-0 4,4'-di((E)-styryl)-1,1'-biphenyl 
• 120926-78-5 (E,E)-4,4'-Bis(3,5-di-tert-butylstyryl)biphenyl 
• 142534-18-7 (Z,Z)-4,4'-Bis(3,5-di-tert-butylstyryl)biphenyl 
• 142534-19-8 (Z,E)-4,4'-Bis(3,5-di-tert-butylstyryl)biphenyl 
• 128825-67-2 4'-((1Z,4Z,9Z,15Z)-13,17-Dihexyl-2,3,7,8,12,18-hexamethyl-porphyrin-5-yl)-biphenyl-4-carbaldehyde 
• 152424-50-5 [4'-(5,5-Dimethyl-[1,3]dioxan-2-yl)-biphenyl-4-yl]-methanol 
• 3731-89-3 4,4'-Bis-(4-hydroxy-phenyliminomethyl)-biphenyl 
• 3525-65-3 4,4'-Bis-cyclohexyliminomethyl-biphenyl 
• 3525-54-0 4,4'-Bis-(4-methoxy-phenyliminomethyl)-biphenyl 
• 3782-72-7 4,4'-Bis-(4-carboxy-phenyliminomethyl)-biphenyl 
• 3881-93-4 4.4'-Bis-(3-hydroxy-4-methoxycarbonyl-phenyliminomethyl)-biphenyl 
• 478490-73-2 (C₆H₄CHNC₆H₄SH)2 
• 639070-46-5 C₅₆H₇₂N₂O₈ 

Relevant academic research and scientific papers

Degradation of fluorescent whitening agents in sunlit natural waters

Stilbene-type fluorescent whitening agents (FWAs), such as the distyryl biphenyl (DSBP) and the diaminostilbene types (DAS 1 and DAS 2), are commonly used in detergents and papers. They are not readily biodegradable, but due to their ability to absorb part of the terrestrial sunlight, they can be photochemically degraded in natural surface waters. Following a fast preceding photoisomerization, the three compounds are degraded by direct photochemical processes yielding mainly aldehydes and alcohols. Their degradation quantum yields are similar, about 10"SUP -4" . Nevertheless, in samples of a eutrophic Swiss lake water, DSBP is photochemically degraded three times faster (t"SUB 1/2" =87 min) in summer noon terrestrial sunlight at 25 degrees C than DAS 1 and DAS 2 (t"SUB 1/2" =278 and 313 min) because of a higher rate of sunlight absorption by the DSBP isomer mixture. All FWAs are degraded faster if the oxygen concentration is increased. Dissolved natural organic material partly inhibits the degradation of DSBP in the reaction with molecular oxygen. The behavior of these compounds illustrates the influence of a preceding isomer equilibrium on degradation rate coefficients. (Authors)

Mn(OAc) 3Induced C-4 Arylations of Quinazoline 3-Oxides with Arylboronic Acids

The use of manganese triacetate as an oxidant component in the C-4 arylations of 2-aryl-quinazoline 3-oxides with arylboronic acids is reported. The new protocol was applied to prepare new 2,4-diarylated quinazoline 3-oxides in good to high yields. The me

Pd-catalyzed oxidative homocoupling of arylboronic acids in WEPA: A sustainable access to symmetrical biaryls under added base and ligand-free ambient conditions

Symmetrical and unsymmetrical biaryls comprises a diverse class of biologically eloquent organic compounds. We herein report, a quick and eco-friendly protocol for the synthesis of biaryls by an oxidative (aerobic) homocoupling of arylboronic acids (ABAs) using Pd(OAc)2 in water extract of pomogranate ash (WEPA) as an efficient agro-waste(bio)-derived aqueous (basic) media. The reactions were executed at ambient aerobic conditions in the absence of external base and ligand to result symmetrical biaryls in excellent yields. The use of renewable media with an effective exploitation of waste, short reaction times, excellent yields of products, easy separation of the products, unnecessating the external base, oxidant, ligand or volatile organic solvents and ambient reaction conditions are the vital insights of the present protocol.

Oxidative and Reductive Cross-Coupling Reactions Catalyzed by an Anionic "ligandless" Palladium Complex

The anionic complex [NBu4][Pd(DMSO)Cl3], which can be synthesized on a gram scale in a single step starting from commercially available starting materials, has been shown to be an active catalyst in the Mizoroki-Heck reaction of aryl halides. We present two new catalytic applications of this complex: the base-free oxidative Heck reaction and the reductive homodimerization of aryl halides. This complex outperformed other palladium salts. In the latter reaction, the catalyst loading could be reduced to 0.01 mol %. The scope of the reactions has been explored, demonstrating the potential of the anionic palladium complex in these catalytic transformations.

Palladium-metalated porous organic polymers as recyclable catalysts for chemoselective decarbonylation of aldehydes

A novel palladium nanoparticle (NP)-metalated porous organic ligand (Pd NPs/POL-xantphos) has been prepared for the chemoselective decarbonylation of aldehydes. This heterogenous catalyst not only has excellent catalytic activity and chemoselectivity, but also holds high activity after 10 runs of reuse. The effective usage of this method is demonstrated through the synthesis of biofuels such as furfuryl alcohol (FFA) via the highly chemoselective decarbonylation of biomass-derived 5-hydroxy-methylfurfural (HMF) with a TON up to 1540. More importantly, 9-fluorenone could be obtained in one step through the decarbonylation of 2-bromobenzaldehyde by using this heterogeneous catalyst.

Palladium(II) complexes with diaminomaleonitrile-based Schiff-base ligands: Synthesis, characterization and application as Suzuki–Miyaura coupling catalysts

The characterization of synthesized Schiff base ligands (L1–L5); (where L1?=?N-salicyliden- 2,3-diamino-cis-2-butenedinitrile, L2?=?3- methoxy-N-salicyliden-2,3-diamino-cis-2-butenedinitrile, L3?=?5-bromo-N-salicyliden-2,3-diamino-cis-2-butenedinitrile, L4?=?5-nitro-N-salicyliden-2,3-diamino-cis-2-butenedinitrile, and L5?=?5-methoxy-N-salicyliden-2,3-diamino-cis-2-butenedinitrile) and their palladium complexes [PdL(PPh3)] (L1–L5) were carried out by FT-IR, UV–vis, 1H NMR, 13C NMR and elemental analysis. The coordination geometry of [PdL3(PPh3)] was determined by single crystal X-ray crystallography. In this structure the palladium center was in a partially distorted NNOP square planar coordination environment. The catalytic potential of the synthesized complexes was evaluated in Suzuki–Miyaura cross-coupling reaction by choosing different arylhalides and phenylboronic acid. The results showed that arylhalides with electron withdrawing substituents were more appropriate in this reaction. In all cases, the desired product of cross coupling Suzuki reaction was the major product. It is also worth to mention that the product of homo-coupling reaction was also observed as a minor product. In this regards, a blank reaction with just phenylboronic acid was performed and the results showed the occurrence of the homo-coupling product in a good yield.

Exfoliation effect of PEG-type surfactant on Pd supported GO (SE-Pd(nanoparticle)/GO) in cascade synthesis of amides: A comparison with Pd(nanoparticle)/rGO

In the presence investigation, a cascade method for the synthesis of primary amides is discussed by the catalysis of Pd supported onto graphene oxide (Pd/GO) nanosheets. Also, the effect of different polyethyleneglycol-type (PEG-type) polyethers including PEG-300, P123 and F127 on the catalytic activity of Pd/rGO is studied in the the reaction of aldehyde and hydroxylamine hydrochloride to give benzamide. Addition of PEG-type polyethers played an important role in raising the catalytic power of Pd(nanoparticle)/GO by exfoliation of GO sheets. The present paper introduces Pd(nanoparticle)/GO as first Pd supported GO for the synthesis of primary amides through this method. This catalyst was highly active, efficient, tolerant, and environmentally benign in one-pot conditions with recyclability at least for 8 runs. Also, this study suggests the prevailing catalytic activity of Pd(nanoparticle)/GO rather to Pd(nanoparticle)/rGO in a comparitive experiment.

Water mediated Heck and Ullmann couplings by supported palladium nanoparticles: Importance of surface polarity of the carbon spheres

Heterogeneous palladium nanoparticle catalysts that are supported on amphiphilic carbon spheres (Pd@CSP) have been utilized for water-mediated Heck coupling reactions of aryl halides with different alkenes under phosphine free as well as aerobic conditions. Furthermore, a variety of Heck coupling reactions using different bases and solvents, including organic polar and non-polar solvents, have been explored. Aryl bromides are also well activated in Heck coupling reactions in organic polar solvent and as well as in water. In addition, Ullmann coupling reactions of aryl iodides have been catalyzed in water with the aid of phase transfer catalysts (PTC) in moderate yields. A plausible mechanism for the catalytic activity of Pd@CSP in the case of the Ullmann reaction is also established. It has been demonstrated that the hydrophobic effects of the catalyst surface play an important role in catalyst activity in water. In addition, the E-factor analysis verified that our present protocol is significantly comparable with other catalytic systems and explains the improved greenness. Moreover, the catalyst described in this process is not only greener, but also retains its significant activity for up to four catalytic cycles for the Heck coupling reactions. The surface polarity of the amphiphilic carbon spheres results in higher activity under these conditions.

Sunlight promoted palladium catalysed Mizoroki-Heck, Suzuki-Miyaura and Sonogashira reactions

The palladium catalysed Mizoroki-Heck, Suzuki-Miyaura and Sonogashira reactions were successfully carried out under irradiation with sunlight. The Heck reaction gives considerable amount of Z product due to photochemical isomerization of initially formed E alkenes. Reaction of methyl 2-iodobenzoate with acrylamide under solar condition furnished 2H-2-benzazepine-1,3-dione rather than the expected derivative of cinnamate while the same reaction with ethyl 2-iodobenzoate gave the desired cinnamide.

Mild and ligand-free Pd(II)-catalyzed conjugate additions to hindered γ-substituted cyclohexenones

Ligand-free cationic Pd(II) catalyst with NaNO3 as an additive is a highly active catalytic system for conjugate additions to sterically hindered γ-substituted cyclohexenones. More challenging γγ- and βγ-substrates also react well to produce products with quaternary centers in good dr. The conjugate additions occur in a diastereoselective fashion under mild, practical and air-stable conditions, using readily available commercial reagents.