2113-58-8

Basic information

• Product Name: 3-NITROBIPHENYL
• Synonyms: 3-NITRODIPHENYL;3-NITROBIPHENYL;TIMTEC-BB SBB007888;M-NITRODIPHENYL;3-Nitobiphenyl;3-nitro-1,1’-biphenyl;3-Nitro-1,1'-biphenyl;3-nitro-1’-biphenyl
• CAS NO: 2113-58-8
• Molecular Formula: C₁₂H₉NO₂
• Molecular Weight: 199.21
• EINECS: 218-305-4
• Product Categories: Nitro Compounds;Nitrogen Compounds;Organic Building Blocks;Building Blocks;Chemical Synthesis;Nitro Compounds;Nitrogen Compounds;Organic Building Blocks
• Mol File: 2113-58-8.mol
• Article Data: 360

Chemical Properties

• Melting Point: 58-60 °C(lit.)
• Boiling Point: 227 °C (35 mmHg)
• Flash Point: 227°C/35mm
• Appearance: /
• Density: 1.1919 (rough estimate)
• Vapor Pressure: 0.000186mmHg at 25°C
• Refractive Index: 1.5880 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 1872195
• CAS DataBase Reference: 3-NITROBIPHENYL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-NITROBIPHENYL(2113-58-8)
• EPA Substance Registry System: 3-NITROBIPHENYL(2113-58-8)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36
• WGK Germany: 3
• RTECS: DV5570000
• Hazardous Substances Data: 2113-58-8(Hazardous Substances Data)

Usage

Chemical Properties

yellow crystalline powder

InChI:InChI=1/C12H9NO2/c14-13(15)12-8-4-7-11(9-12)10-5-2-1-3-6-10/h1-9H

Upstream product

• 4085-18-1 4-amino-3-nitrobiphenyl 
• 20241-06-9 1-(3-nitrophenyl)-3,3-dimethyltriazene 
• 104-15-4 toluene-4-sulfonic acid 
• 71-43-2 benzene 
• 99-09-2 3-nitro-aniline 
• 16278-29-8 3-nitrobenzenediazonium 
• 2243-47-2 3-biphenyl amine 
• 100-42-5 styrene 
• 929-11-3 1,4-dinitro-1,3-butadiene 
• 585-79-5 m-nitrobromobenzene 
• 98-80-6 phenylboronic acid 
• 595-90-4 tetraphenyltin(IV) 
• 934-56-5 trimethyl(phenyl)stannane 
• 98-95-3 nitrobenzene 

Downstream Products

• 121-92-6 3-nitrobenzoic acid 
• 101366-50-1 3'-nitrobiphenyl-4-sulfonyl chloride 
• 54852-73-2 3-ethoxybiphenyl 
• 176032-41-0 N-([1,1'-biphenyl]-3-yl)-3-nitropyridine-2-amine 
• 1399050-18-0 C₁₉H₁₆N₃⁽¹⁺⁾*Cl^(1-) 
• 4969-04-4 3,3'''-diphenyl-p-quaterphenyl 
• 4740-51-6 m-sexiphenyl 
• 20442-79-9 3-iodo-1,1'-biphenyl 
• 1166-18-3 meta-quaterphenyl 
• 59080-33-0 2,4,6-tribromobiphenyl 
• 53592-10-2 2,4-dibromo-1,1'-biphenyl 
• 2113-54-4 N-(biphenyl-3-yl)acetamide 
• 5737-85-9 3'-nitro-biphenyl-4-carboxylic acid 
• 180003-61-6 6-phenyl-2,3,3-trimethylindolenine 

Relevant articles and documents

Rapid microwave-promoted catalyst- and solvent-free suzuki-type coupling reaction

The catalyst- and solvent-free Suzuki coupling reaction of sodium tetraphenylborate with hypervalent iodonium salts was achieved under microwave irradiation in the absence of a base. A convenient method for formation of carbon-carbon bonds afforded good yields in a short time. Copyright Taylor & Francis Group, LLC.

Stainless steel mesh-GO/Pd NPs: Catalytic applications of Suzuki-Miyaura and Stille coupling reactions in eco-friendly media

The immobilization of palladium nanoparticles (Pd NPs) on stainless-steel mesh is described in two short steps via deposition of graphene oxide (GO) on the stainless-steel mesh (mesh-GO) by electrophoretic deposition (EPD), preparation of Pd NPs using laser ablation in liquids (LAL) and finally the immobilization of Pd NPs on the mesh-GO by immersion in a Pd NP colloidal solution. The novel, efficient and reusable mesh-GO/Pd catalyst was characterized by various techniques such as SEM, EDS, UV-Vis and FT-IR spectroscopy and its catalytic activity was investigated for the Suzuki-Miyaura and Stille coupling reactions in ethanolic water.

Biosynthesis of supported Pd nanoparticles using poplar leaf as a reducing agent and carrier: A green route to highly efficient and reusable Suzuki coupling reaction catalyst

A green process for the synthesis of supported Pd nanoparticles (NPs) using poplar leaf extract (PLE) as a reducing agent and the extracted residue of poplar leaf (RPL) as a carrier is reported. The Pd/RPL nanocomposites were characterized by XRD, TEM, SEM, EDS, XPS, FTIR, and ICP-AES. The spherical Pd NPs had a mean particle size of 3.1 nm and were evenly distributed on the RPL surface. More importantly, the Pd/RPL nanocomposites were used as a heterogeneous catalyst, which presented superior catalytic activity for the Suzuki coupling reaction. In addition, only a slight loss in the catalytic activity was observed after six recycles.

Graphene-Supported Palladium Complex: A Highly Efficient, Robust and Recyclable Catalyst for the Suzuki-Miyaura Cross-Coupling of Various Aryl Halides

We present a novel strategy based on the immobilization of a palladium complex on reduced graphene oxide for the development of a heterogeneous catalytic system with high efficiency and good recyclability. The prepared catalyst was tested for Suzuki-Miyaura cross-coupling reactions and shown to have a high catalytic efficiency, giving 83-98% conversion of the reactants under mild conditions. Moreover, it could be readily recycled and reused several times without significant loss of activity.

Magnetically recoverable 2-(aminomethyl)phenols-modified nanoparticles as a catalyst for Knoevenagel condensation and carrier for palladium to catalytic Suzuki coupling reactions

A class of magnetic nanoparticles modified by 2-(aminomethyl)phenols has been successfully designed and synthesized as a reusable catalyst for Knoevenagel reaction. What's more, such nanomaterial also proved as suitable carrier for immobilization of palladium nanoparticles and the obtained composite exerted potent catalytic activity in Suzuki coupling reactions. Both of the (aminomethyl)phenols-modified nanoparticles and its related palladium nanocatalyst could be easily separated and reused for several consecutive runs by magnetic decantation without significant loss of their catalytic efficiency.

Palladium nanoparticles supported on Layered Hydroxide Salts and their Use in Carbon-Carbon coupling organic reactions

Palladium nanoparticles supported on zinc hydroxide salts were prepared by intercalation of [PdCl6]2- and its further reduction with ethanol under reflux. All the materials were completely characterized by atomic absorption spectroscopy (AAS), X-ray diffraction (XRD), thermogravimetric/ derivative thermogravimetric (TG/DTG) analyses, scanning electron microscopy (SEM), UV-Visible spectrometry and transmission electron microscopy (TEM). TEM analysis confirmed that the palladium nanoparticles were properly supported. The material containing supported palladium nanoparticles was used to promote Heck and Suzuki coupling reactions starting from aryl halides, with isolated yields of 98, 75 and 62percent of biphenyl, cinnamic acid and 3-nitrobiphenyl, respectively.

Polystyrene-Supported PPh3 in Monolithic Porous Material: Effect of Cross-Linking Degree on Coordination Mode and Catalytic Activity in Pd-Catalyzed C?C Cross-Coupling of Aryl Chlorides

Hybridization of porous synthetic polymer and sophisticated ligands play an important role in transition-metal catalysis for chemical transformations at laboratory and industrial levels. A monolithic porous polymer, which is a single piece with continuous macropores, is desired for high permeability, fast mass transfer properties, high stability, and easy modification. Herein, we first develop a monolithic porous polystyrene containing three-fold cross-linked PPh3 (M-PS-TPP) for transition-metal catalysis. The monolithic and macroporous structure of M-PS-TPP was fabricated via polymerization-induced phase separation using porogenic solvent. Moreover, the M-PS-TPP was synthesized using different feed ratios of divinylbenzene (DVB) for site-isolation and mono-P-ligating behavior of PPh3. 31P CP/MAS NMR analysis revealed that the different selectivity of M-PS-TPPs was obtained in formation of mono-P-ligation toward PdII. The macroporous properties and controlled mono-P-ligating behavior of M-PS-TPP facilitated the challenging Pd-catalyzed Suzuki-Miyaura cross-coupling reaction of chloroarenes.

Layered double hydroxide-supported nanopalladium: An efficient and reusable catalyst for Suzuki coupling of aryl iodides and bromides at room temperature

Layered double hydroxide-supported nanopalladium (LDH-Pd0) is an effective catalyst for Suzuki cross-coupling of a wide range of aryl iodides and bromides with arylboronic acids at room temperature. The catalyst is reused for four cycles with consistent activity. Georg Thieme Verlag Stuttgart.

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Nickel-glycerol: An efficient, recyclable catalysis system for Suzuki cross coupling reactions using aryl diazonium salts

Nickel catalysed Suzuki reactions of phenyl boronic acids with aryl diazonium salts in glycerol as a reaction medium are reported. Various aryl diazonium salts were efficiently reacted with aryl boronic acids under optimized conditions to give the respective diaryl compounds in good to excellent yields. The base free conditions and use of glycerol as a solvent, which can be recycled successfully for up to five consecutive cycles, make the present protocol environmentally benign in nature.

Photo-oxidation of 4-aminobiphenyl

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Synthesis of biguanide-functionalized single-walled carbon nanotubes (SWCNTs) hybrid materials to immobilized palladium as new recyclable heterogeneous nanocatalyst for Suzuki-Miyaura coupling reaction

Pd supported on biguanide(metformine)-functionalized single-walled carbon nanotubes (SWCNT-Met/Pd2+) hybrid materials was fabricated for the first time. The prepared heterogeneous nanocatalyst was characterized by XRD, FT-IR, SEM, TGA and TEM. The catalytic activity of the prepared catalyst was investigated by employing Suzuki-Miyaura coupling reaction as a model reaction. A series of biphenyl compounds were synthesized through the Suzuki-Miyaura reaction using SWCNT-Met/Pd2+ as catalyst. The yields of the products were in the range from 80% to 95%. The catalyst can be readily recovered and reused at least 5 consecutive cycles without significant loss its catalytic activity.

Labile imidazolium salt protected palladium nanoparticles

An imidazolium (Im) salt with two long alkyl substituents at N atoms is employed to prepare cubelike palladium nanoparticles (PdNPs). The bilayer nature of the capped Im salts is characterized by thermogravimetric analysis and NMR studies. These capped Im salts are labile, as evidenced by their displacement reaction with dimethylaminopyridine, and the observation of fast exchange between those free and capped Im salts on the NMR time scale. NMR results also show that these capped Im salts exhibit different diffusion rates, and interesting spinning rate dependent chemical shifts. These cubelike PdNPs could catalyze the Suzuki coupling of aryl chlorides and boronic acids with high yields in 10 min, even at room temperature.

Active immobilized palladium catalyst based on multiporous amphiphilic graft copolymer

Poly(vinylidene fluoride)-g-poly(dimethylaminoethyl methacrylate) (PVDF-g-PDMAEMA)/camphor system produces thermoreversible gel and leaching of camphor with cyclohexane yields amphiphilic multiporous material characterized from scanning electron microscopy (SEM), mercury intrusion porosimetry (MIP) and nitrogen adsorption porosimetry. Pd nanoparticles (Pd NPs, dia. 2.5-4.5 nm) are grown on this porous material by adsorption of Pd(OAc)2 followed by reduction with hydrazine. MIP and nitrogen porosimetry show that the xerogels are multiporous in nature and the pore size decreases in the Pd NPs captured sample. The BET surface area of the Pd NPs captured dried gel (24.3 m 2 g-1) is lower than that of pure gel (32.5 m2 g-1) due to the blocking of some pores by Pd NPs. The Pd NPs captured amphiphilic porous PVDF-g-PDMAEMA act as an effective catalyst for aerobic ligand free Suzuki coupling of aryl halides (X = I, Br and Cl) in aqueous medium.

Preparation of magnetic chitosan-supported palladium-5-amino-1H-tetrazole complex as a magnetically recyclable catalyst for Suzuki-Miyaura coupling reaction in green media

The utilization of various tetrazoles as efficient ligands is a promising method for the functionalization of tetrazole-based heterogeneous catalysts. Their combination with magnetic species and natural supports exposes huge opportunities for the practical applications of heterogeneous catalysts. In this study, a green and novel strategy is applied to synthesize Fe3O4 magnetic nanoparticles (MNPs) incorporated with chitosan (CS) and 5-amino-1H-tetrazole with a long tail ((3-chloropropyl)trimethoxysilane) to immobilize palladium catalyst designated as Fe3O4–CS@tet-Pd(II). The prepared Fe3O4–CS@tet-Pd(II) was used as an efficient and magnetically recyclable catalyst for the Suzuki-Miyaura cross-coupling reaction (SMCR) using a mixture of EtOH/H2O as green media under aerobic conditions. All the expected products were obtained in high yields, indicating the high efficiency of this catalyst for the preparation of various biaryls by SMCR. Various latest techniques were used to characterize Fe3O4–CS@tet-Pd(II), e.g., Fourier-transform infrared spectroscopy (FT-IR), energy-dispersive X-ray spectroscopy (EDS) elemental mapping, X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning TEM (STEM), high resolution TEM (HR-TEM), vibrating sample magnetometer (VSM), fast Fourier transform (FFT), thermogravimetric analysis (TGA), etc. This study presents a unique example of 5-amino-1H-tetrazole grafted on Fe3O4–CS, which can easily be separated using an external magnet and reused five times without significant decrease of catalytic activity. In addition, the introduced method has significant advantages such as the utilization of natural and inexpensive materials, easy work-up, high yields of products, and high catalytic activity.

Synthesis of bulky, electron rich hemilabile phosphines and their application in the Suzuki coupling reaction of aryl chlorides

Novel electron rich, amine functionalised phosphines have been prepared and shown to belong to an unusual class of ligands that can activate palladium complexes to catalyse the Suzuki coupling reaction of chloroarenes.

Highly active and magnetically recoverable Pd-NHC catalyst immobilized on Fe3O4 nanoparticle-ionic liquid matrix for suzuki reaction in water

Pd-NHC-ionic liquid matrix was immobilized into ionic liquid layers coated on the surface of Fe3O4. The immobilized Pd-NHC was used as a catalyst for Suzuki coupling. The catalyst exhibited both high catalytic activity and stability for the coupling between aryl bromide and arylboronic acid in water. This catalyst was simply recovered by an external permanent magnet and recycled without a significant loss in the catalytic activity.

Preparation and characterization of new palladium complex immobilized on (chitosan)/PoPD biopolymer and its catalytic application in Suzuki cross-coupling reaction

The present work reports the design, synthesis, and characterization of palladium complex immobilized on chitosan/poly(o-phenylenediamine) (CS-PoPD-Pd) for the catalytic application in the Suzuki–Miyaura C-C cross-coupling reaction through a nontoxic, inexpensive, eco-friendly, and practical method. Fourier-transform–infrared (FT-IR) spectroscopy, scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDX), elemental mapping, X-ray diffraction (XRD), and inductively coupled plasma-optical emission spectrometry (ICP-OES) techniques were used for analyzing the prepared catalyst. Characterization studies showed that CS-PoPD-Pd was successfully synthesized according to our design. CS-PoPD-Pd composite demonstrated high product yield and high turnover number (TON) and turnover frequency (TOF) values with small catalyst loading for the Suzuki–Miyaura C-C cross-coupling reaction under mild reaction conditions. Besides, the synthesized CS-PoPD-Pd composite could be readily recycled and reused for at least five runs without discernible loss of its catalytic activity.

'Awaken' aryl sulfonyl fluoride: a new partner in the Suzuki-Miyaura coupling reaction

An example of the activation of the -SO2F group, which is traditionally considered a stable group even in the presence of a transition metal, is described using a novel partner in the Suzuki-Miyaura coupling reaction catalyzed by Pd(OAc)2 and Ruphos as ligands. The products showed good to outstanding yields and broad functional group compatibility under optimal conditions. The sequential synthesis of non-symmetric terphenyls and the gram grade process highlight the approach's synthetic utility. DFT calculations have shown that Pd0 prefers to insert between C-S bonds rather than S-F bonds. This journal is

Polydopamine-Encapsulated Dendritic Organosilica Nanoparticles as Amphiphilic Platforms for Highly Efficient Heterogeneous Catalysis in Water

Aqueous heterogeneous catalysis is a green, sustainable catalytic process that attracts increasing attention, but it often suffers from poor mass transfer, substrate adsorption and catalyst dispersion. Herein, we synthesized a type of amphiphilic core-shell catalysts with a hydrophilic polydopamine (PDA) shell and a hydrophobic dendritic organosilica nanoparticle (DON) core for heterogeneous catalysis in water. The hydrophilic shell allowed the catalyst dispersing well in water, and the hydrophobic core facilitated the absorption of organic reactants. The hierarchical core-shell structure facilitated rational arrangement of the location of catalytic species to match the reaction sequence. The obtained metal, enzyme and metal-enzyme amphiphilic catalysts demonstrated improved stability, selectivity and activity in aqueous reactions, including Pd-catalyzed cross-couplings (Suzuki, Liebeskind-Srogl, Heck and Sonogashira), enzymatic enantioselective reduction, chemoenzymatic cascade synthesis of chiral compounds and chemoenzymatic cascade degradation of organophosphates. The amphiphilic catalysts could be easily in situ recovered, and their high catalytic performance was sustained for five cycles.