108321-69-3

Basic information

• Product Name: 2-CHLOROBIPHENYL-CHLOROPHENYL-RING-UL-
• Synonyms: 2-CHLOROBIPHENYL-CHLOROPHENYL-RING-UL-
• CAS NO: 108321-69-3
• Molecular Formula: C16H22O4
• Molecular Weight: 278.34
• Mol File: 108321-69-3.mol
• Article Data: 153

Chemical Properties

• Appearance: /toluene solution
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-CHLOROBIPHENYL-CHLOROPHENYL-RING-UL-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLOROBIPHENYL-CHLOROPHENYL-RING-UL-(108321-69-3)
• EPA Substance Registry System: 2-CHLOROBIPHENYL-CHLOROPHENYL-RING-UL-(108321-69-3)

Safety Data

• Hazard Codes: F,Xn,R,T
• Statements: 11-38-48/20-63-65-67-23/24/25
• Safety Statements: 36/37-62-45-36/37/39-16
• RIDADR: UN 2910 7
• WGK Germany: 3
• Hazardous Substances Data: 108321-69-3(Hazardous Substances Data)

Upstream product

• 110-86-1 pyridine 
• 108-90-7 chlorobenzene 
• 94-36-0 dibenzoyl peroxide 
• 92-52-4 biphenyl 
• 90-41-5 2-phenylaniline 
• 938-81-8 N-nitrosoacetanilide 
• 861-97-2 bis(2-phenylbenzoyl) peroxide 
• 1489-24-3 N-<(o-phenylthio)phenyl>formamide 
• 591-50-4 iodobenzene 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 71-43-2 benzene 
• 108-95-2 phenol 
• 95-50-1 1,2-dichloro-benzene 
• 64146-89-0 diphenylchloronium hexafluorophosphate 

Downstream Products

• 90-41-5 2-phenylaniline 
• 59964-94-2 (biphenyl-2-yl)hydrazine 
• 606-97-3 2-benzyl-1,1'-biphenyl 
• 10271-65-5 2-(phenylethynyl)-1,1'-biphenyl 
• 14925-09-8 2-(N-methylamino)-1,1'-biphenyl 
• 860597-66-6 2-(2'-amino-biphenyl-4-carbonyl)-benzoic acid 
• 172723-84-1 2-(2'-hydroxy-biphenyl-4-carbonyl)-benzoic acid 
• 91306-98-8 2-(2'-Chloro-biphenyl-4-yl)-1-(4-chloro-phenyl)-5-methyl-1H-pyrrole 
• 73844-66-3 5-<4'-(2-chlorophenyl)phenyl>-5-hydroxy-3-methyl-2,5-dihydrofuran-2-one 
• 58182-63-1 [14C]-Itanoxone 
• 73844-62-9 4-<4'-(2-chlorophenyl)phenyl>-4-oxo-2-methylenebutanoic acid 

Relevant articles and documents

Azaindoles as Zinc-Binding Small-Molecule Inhibitors of the JAMM Protease CSN5

CSN5 is the zinc metalloprotease subunit of the COP9 signalosome (CSN), which is an important regulator of cullin-RING E3 ubiquitin ligases (CRLs). CSN5 is responsible for the cleavage of NEDD8 from CRLs, and blocking deconjugation of NEDD8 traps the CRLs in a hyperactive state, thereby leading to auto-ubiquitination and ultimately degradation of the substrate recognition subunits. Herein, we describe the discovery of azaindoles as a new class of CSN5 inhibitors, which interact with the active-site zinc ion of CSN5 through an unprecedented binding mode. The best compounds inhibited CSN5 with nanomolar potency, led to degradation of the substrate recognition subunit Skp2 in cells, and reduced the viability of HCT116 cells.

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Dechlorination of hexachlorobiphenyl by using potassium-sodium alloy

2,2',4,4',5,5'-Hexachlorobiphenyl (HCB) was dechlorinated with potassium-sodium (K-Na) alloy under an inert gas atmosphere. Solvent effect was observed in the reaction. Dechlorination yields in benzene and cyclohexane were 99.9998% and 99.99996%, respecti

Microwave-assisted suzuki cross-coupling reactions using dimeric ortho-palladated complex of tribenzylamine

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Nicotine functionalized-silica palladium (II) complex: a highly efficient, environmentally benign and recyclable nanocatalyst for C-C bond forming reactions under mild conditions

An environmentally friendly silica-grafted nicotine-based palladium(II) complex was successfully prepared and evaluated for the first time as novel and efficient nanocatalyst in C-C bond forming reactions. Grafted-nicotine in this catalytic system plays an important role, and as an effective ligand and a quaternary ammonium salt demonstrates an efficient stabilizing effect on the Pd(II) species by a synergistic effect of coordination and electrostatic interactions. The catalyst was well characterized by FT-IR, CHN, XRD, TEM, SEM–EDX, ICP and TG analysis, and demonstrated a highly efficient catalytic activity in the reaction system under phosphine-free and low Pd loading conditions, and the coupled products were produced in good to excellent yields. Furthermore, the catalyst can be easily recovered and reused without a significant loss of activity. Copyright

Synthesis of a new palladium salt using N-benzyl DABCO chloride and its application in Suzuki reaction

A palladium catalyst was synthesized using N-benzyl DABCO chloride and palladium chloride. The structure of this catalyst was characterized and then the catalyst was used in Suzuki cross- coupling reaction of different aryl halides with arylboronic acids. All substrates afforded the corresponding products in good to high yields in the presence of low amounts of the catalyst. Under the heating conditions employed, cheaper and more available aryl chlorides gave relatively high yields in the Suzuki reaction. Copyright

Silica-acac-supported palladium nanoparticles as an efficient and reusable heterogeneous catalyst in the Suzuki-Miyaura cross-coupling reaction in water

Supported Pd nanoparticles on acetyl acetone modified silica gel was prepared and its catalytic application in the Suzuki-Miyaura reaction of various aryl halides with phenylboronic acid was investigated. The reaction was carried out in water as solvent under green conditions in the presence of NaHCO 3 as the base. The catalyst was characterized by a combination of powder XRD, XPS, TEM and SEM. The catalyst is not sensitive to air and moisture, so reactions were carried out without using inert atmosphere. The catalyst can be reused up to six times without significant loss of catalyst activity. The cumulative turnover number (TON) over six runs is 13525. Indian Academy of Sciences.

A new advanced method for heterogeneous catalysed dechlorination of polychlorinated biphenyls (PCBs) in hydrocarbon solvent

The dechlorination of PCBs with solid hydrazine hydrochloride catalysed by palladium, in an organic solvent, yields biphenyl in short reaction times. The catalyst system can be efficiently reused for several cycles. Ultrasonication of the heterogeneous catalysed reaction increases the dechlorination rate remarkably. The reactivity of the C-Cl bond on the PCB ring are in the order meta>para?ortho.

Insights into the Suzuki-Miyaura Reaction Catalyzed by Novel Pd?Carbene Complexes. Are Palladium?Tetra- carbene Entities the Key Active Species?

The assumption that the real active species involved in the Suzuki-Miyaura reaction are homogeneous, heterogeneous or both is often proposed. However a lack in the characterization of true catalytic entities and their monitoring makes assumptions somewhat elusive. Here, three families of palladium(II) complexes bearing bisNHC, bispyridyl and bisphosphine ligands were synthesized in order to get new insights into the formation of active species in the Suzuki-Miyaura reaction. Their comparative catalytic study reveals that the nature of the ligands as well as their spacer lengths are pivotal parameters governing the performance. All complexes evolve to Pd NPs under reaction conditions, and an orthogonal behavior is observed for two bisNHC complexes that form homoleptic tetracarbene species. Notably, these species are presumably involved in a new catalytic modus operandi. This ligand-controlled reactivity and the formation of tetracarbene species open new routes towards the design of novel cross-coupling catalysts via the mastering of highly-active catalytic species.

Salicylaldehyde-stabilized palladium nanoparticles for highly efficient suzuki-miyaura reaction at room temperature

Pd-catalyzed Suzuki-Miyaura cross-coupling reactions promoted by simple and commercial salicylaldehyde-based ligands were investigated. The effect of the ligands was evaluated and the reaction conditions were optimized. Moreover, the physical nature of the palladium was determined by TEM analysis and poison tests. It demonstrated that this catalytic system can be reused for ten consecutive runs and showed excellent activities toward aryl bromides with arylboronic acids at room temperature in air.

Synthesis of substituted biaryls via Suzuki, Stille and Hiyama cross-coupling and homo-coupling reactions by CN-dimeric and monomeric ortho-palladated catalysts

The catalytic activity of dimeric [Pd{C6H2(CH 2CH2NH2)-(OMe)2,2,3}(μ-Br)] 2 and monomeric [Pd{C6H2(CH2CH 2NH2)-(OMe)2,2,3}Br(PPh3)] complexes as efficient, stable and air- and moisture-tolerant catalysts was investigated in the Suzuki, Stille and Hiyama cross-coupling and homo-coupling reactions of various aryl halides. Substituted biaryls were produced in excellent yields in short reaction times using catalytic amounts of these complexes. The monomeric complex was demonstrated to be more active than the corresponding dimeric catalyst for the cross-coupling reaction of unreactive aryl bromides and chlorides. The combination of homogeneous metal catalysts and microwave irradiation gave higher yields of products in shorter reaction times. Copyright

Oriented Au nanoplatelets on graphene promote Suzuki-Miyaura coupling with higher efficiency and different reactivity pattern than supported palladium

Facet 1?1?1 oriented Au nanoplatelets (20–40?nm wide, 3–4?nm height) grafted on graphene (Au￣/fl-G) are about three orders of magnitude more efficient than Pd nanoparticles supported on graphene to promote Suzuki-Miyaura coupling. In contrast to Pd cataly

Application of a dimeric ortho-palladated complex of tribenzylamine as an efficient catalyst in microwave-assisted Hiyama coupling reactions

The activity of [Pd{C6H4(CH2N(CH 2Ph)2)}(Iμ-Br)]2 complex was investigated in cross-coupling reactions of triethoxy(phenyl)silane with various aryl halides under microwave irradiation. This complex is an efficient and stable catalyst for the synthesis of substituted biphenyls that is non-sensitive to air and moisture. The combination of dimeric complex as homogenous catalyst, microwave irradiation, DMF as microwave-active polar solvent and TBAF as microwave-active additive led to excellent yields in short reaction times. Copyright

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Ligand-controlled chemoselectivity in potassium tert-amylate-promoted direct C-H arylation of unactivated benzene with aryl halides

Direct C-H arylation of unactivated benzene with aryl halides under various simple ligands (EDA, DMEDA, ethylene glycol, etc.) in the presence of potassium tert-amylate (t-AmOK) base at mild temperature (80 °C) have been developed. This transition-metal-free radical cross-coupling offers an efficient way to synthesize various biaryls in good yields through base-promoted homolytic aromatic substitution. And mechanistic investigations have provided insight into the chemoselectivity of couplings between haloiodobenzenes and benzene and showed that phenanthroline and its derivatives not only initiate these radical reactions like most of other ligands (EDA, DMEDA, ethylene glycol, etc.), but also participate in the electron transfer process of biaryl radical anion intermediates.

Selective Mono-Alkylation and Arylation of Dichlorobenzenes by Palladium-Catalyzed Grignard Cross-Coupling

Palladium(II)-phosphine complexes, especially PdCl2(dppf) where dppf stands for 1,1'-Bis(diphenylphosphino)ferrocene, are effective catalysts for the cross-coupling of Grignard reagents with dichlorobenzenes to produce selectively mono-alkylated and arylated benzenes.The addition of ligands is also effective for the cross-coupling of Grignard reagents containing a β-hydrogen(s).

Application of ortho-palladated homoveratrylamine complex containing mixed phosphorus-nitrogen donors in the Suzuki reaction

The catalytic activity of [Pd{C6H2(CH 2CH2NH2)-(OMe)2,3,4}Br(PPh 3)] monomeric ortho-palladated complex of homoveratrylamine and triphenylphosphine was investigated in the Suzuki cross-coupling reaction of various aryl halides with aryl boronic acids. The substituted biaryls were produced in excellent yields using a catalytic amount of this complex in ethanol at 60°C.

PdCl2 Immobilized on Poly(styrene-co-maleimide) as an Effective Heterogeneous Catalyst for Suzuki Cross-Coupling Reaction

Abstract: Poly(styrene-co-maleic anhydride) (SMA) was reacted with 4-amino-6-methyl-3-thioxo-1,2,4-triazine-5-one to obtain the corresponding imide [SMI] which was used as a substrate for immobilization of PdCl2 and preparation of palladium nanoparticles (PdNPs). The supported PdNPs were fully characterized using scanning electron microscopy (SEM), energy dispersive X-ray (EDAX) and FTIR spectroscopy, and inductively coupled plasma spectrometry (ICP). The catalytic efficiency of the PdNPs was evaluated examined successfully in one the established and useful reaction so-called the Suzuki cross-coupling reaction involving the reaction of various aryl halides with phenylboronic acid in water. The advantages of this procedure include easy recovery and efficient reusability of the expensive PdNPs, high yields of the cross coupled products, short reaction times, and use of water as a green solvent for a wide range of substrates.

Hydrogenolysis of polychlorinated biphenyls by sodium borohydride with homogeneous and heterogeneous nickel catalysts

The hydrogenolysis (hydrodechlorination) of a series of pure PCB congeners with sodium borohydride was studied. In the absence of nickel compounds, very little reaction occurred, but in the presence of solid Raney-type nickel or in the presence of a soluble Ni(0)triphenylphosphine complex, extensive hydrogenolysis occurred at ambient temperatures in DMF. The selectivity of one congener versus another was studied and found to be low. The selectivity for 2-, 3-, and 4-chloro displacement from di- and trichlorobiphenyls in the presence of Ni(0) complexes, however, was found to be high. The selectivities are interpreted with respect to the known mechanism of oxidative addition of aryl halides with Ni(0) complexes.

Triazole-Functionalized Silica Supported Palladium(II) Complex: A Novel and Highly Active Heterogeneous Nano-catalyst for C–C Coupling Reactions in Aqueous Media

Abstract: Two novel triazole-modified silica supports A and B were successfully prepared via “click” reaction of azide-functionalized SiO2 with propargyl alcohol (A) and propargyl amine (B), in which the click-triazole as an important functional entity, in addition to a molecular linker, provides capabilities of metal coordination as an excellent chelator. Treatment of the resulting click-supports with Pd(OAc)2 afforded the click-catalysts A and B, which were well characterized and evaluated in Suzuki–Miyaura coupling in terms of activity and recyclability in H2O/EtOH solvent. The catalyst A showed more reasonable results and so, was applied as a highly efficient and recyclable catalyst in the coupling reactions of various aryl halides with phenylboronic acid under phosphine-free and low Pd loading conditions. Graphical Abstract: Two novel nano pd-catalysts were successfully prepared by immobilization of Pd(OAc)2 onto the silica supports containing the nitrogen-rich triazole chelators and were investigated in Suzuki–Miyaura coupling in aqueous solvent.

Proline-functionalized chitosan-palladium(ii) complex, a novel nanocatalyst for C-C bond formation in water

An environmentally friendly palladium-based catalyst supported on proline-functionalized chitosan was successfully prepared and evaluated as a heterogeneous nanocatalyst in the Suzuki cross-coupling reaction of various aryl halides with phenylboronic acid. The catalyst was characterized by FT-IR, FE-SEM, TEM, XRD, SEM-EDX, ICP and TGA techniques and exhibited reasonable catalytic activity in the reaction system, producing substituted biaryls in good to excellent yields. In addition, the catalyst could be recovered in a facile manner from the reaction mixture and recycled several times.

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Cobalt-catalyzed direct arylation of unactivated arenes with aryl halides

Inexpensive and simple: The direct arylation of unactivated arenes with aryl halides has been carried out with [Co(acac)3] as the catalyst and LiHMDS as the base. The corresponding biaryl compounds have been prepared in good to excellent yields and at a relatively low reaction temperature (see scheme; acac=acetylacetonate, LiHMDS=lithium bis(trimethylsilyl)amide). An intramolecular direct arylation has also been achieved under the same conditions.

Ni(cod)2/PCy3-catalyzed cross-coupling reactions of dihaloarenes with arylboronic acids

The Ni(0)-catalyzed cross-coupling reactions of dihaloarenes with one equivalent of arylboronic acids is described. The Ni(cod)2/PCy 3 was identified as the best catalyst system to achieve a double cross-coupling reaction, likely via an efficient preferential oxidative addition. Georg Thieme Verlag Stuttgart New York.

Ferrocene catalysed C–H arylation of arenes and reaction mechanism study using cyclic voltammetry

Ferrocene catalysed C–H arylation of benzene using aryldiazonium salt is studied. Yield of biphenyl in this reaction was found to be better than some of the known methods. Aryldiazonium salts with electron withdrawing groups produced excellent yields (upto 85%) in C–H arylation. Applicability of this reaction was studied on several arenes and heteroarene such as benzene, naphthalene, anthracene, pyrene and pyridine. Catalytic role of ferrocene in aryl radical formation was studied by cyclic voltammetry of phenyldiazonium tetrafluoroborate. In presence of ferrocene more radical formation was observed. This reaction model works at ambient temperature and features the use of inexpensive catalyst for the synthesis of biaryl derivatives.

Synthesis and characterization of palladium nanoparticles immobilized on graphene oxide functionalized with triethylenetetramine or 2,6-diaminopyridine and application for the Suzuki cross-coupling reaction

Graphene oxide (GO) was functionalized with two organic ligands, triethylenetetramine (TETA) or 2,6-diaminopyridine (DAP), followed by palladium nanoparticles (Pd NPs) for the synthesis of Pd NPs/GO-TETA and Pd NPs/GO-DAP nanocomposites, respectively. The two heterogeneous nanocomposites were fully characterized and their efficiency was investigated for C[sbnd]C bond formation for the synthesis of biaryl compounds via the Suzuki cross-coupling reaction of aryl halides with arylboronic acid derivatives. The obtained results indicated that the Pd NPs/GO-TETA nanocomposite was more effective in the Suzuki coupling reaction as compared to Pd NPs/GO-DAP. Thus, the Suzuki cross-coupling reaction of different aryl halides with arylboronic acid derivatives using Pd NPs/GO-TETA nanocomposite catalyst in the presence of Na2CO3 as base in DMF/H2O (1/1) as solvent at 90 °C was carried out to afford the desired biaryl compounds in high to excellent yields (81–100%) and short reaction times (10–90 min). Additionally, Pd NPs/GO-TETA nanocomposite can be recovered and reused for 8 consecutive runs without any apparent loss of its catalytic activity, proving its high stability and potential use in organic transformations.

Preparation of an Efficient and Recoverable Catalyst through Immobilization of PdCl2 on Modified Poly(styrene-co-maleic anhydride) for the Suzuki Cross-Coupling Reaction

Abstract: A copolymer of styrene and maleic anhydride was modified via reaction with 4-amino-5-methyl-4H-1,2,4-triazole-3-thiol, and palladium(II) chloride was then immobilized on the modified copolymer. The resulting nanocatalyst was characterized by scanning electron microscopy (SEM), energy dispersive spec-troscopy, X-ray (EDAX) and inductively coupled plasma (ICP) analyses, and FT-IR, 1H NMR, and 13C NMR spectroscopic data. The catalytic efficiency of the new palladium nanoparticles was successfully examined in the Suzuki cross-coupling reaction of various aryl halides with phenylboronic acid in water. The advantages of this strategy were easy recovery and efficient reusability of the expensive PdNPs, high yields of the cross-coupling products, short reaction times, and the use of water as a solvent for a wide range of substrates.

Buchwald ligand-assisted Suzuki cross-coupling of polychlorobenzenes

Screening of four Buchwald ligands for the cross-coupling of isomeric di-, tri- and tetrachlorobenzenes with arylboronic acids revealed that good yields of exhaustive substitution can be best provided by 2-dicyclohexylphosphino-2′-(dimethylamino) biphenyl (DavePHOS).