182169-63-7

Basic information

• Product Name: 1-(4'-METHOXY[1,1'-BIPHENYL]-3-YL)ETHANONE
• Synonyms: 1-(4'-METHOXY-BIPHENYL-3-YL)-ETHANONE;1-(4'-METHOXY[1,1'-BIPHENYL]-3-YL)ETHANONE;AKOS BAR-0239;1-[3-(4-methoxyphenyl)phenyl]ethanone
• CAS NO: 182169-63-7
• Molecular Formula: C15H14O2
• Molecular Weight: 226.27
• Mol File: 182169-63-7.mol

Chemical Properties

• Boiling Point: 383.4 °C at 760 mmHg
• Flash Point: 175.5 °C
• Appearance: /
• Density: 1.076 g/cm³
• CAS DataBase Reference: 1-(4'-METHOXY[1,1'-BIPHENYL]-3-YL)ETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4'-METHOXY[1,1'-BIPHENYL]-3-YL)ETHANONE(182169-63-7)
• EPA Substance Registry System: 1-(4'-METHOXY[1,1'-BIPHENYL]-3-YL)ETHANONE(182169-63-7)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 182169-63-7(Hazardous Substances Data)

Usage

Type of Compound

Organic compound and a ketone derivative

Physical State

White crystalline solid

Odor

Sweet, fruity

Usage

a. Fragrance ingredient in perfumes
b. Production of pharmaceuticals and other organic compounds
c. Intermediate in the synthesis of various organic molecules

Applications

a. Organic chemistry research
b. Building block for the development of new materials and compounds

Safety Precautions

Handle with care and follow safety protocols due to potential hazards

Upstream product

• 5720-07-0 4-methoxyphenylboronic acid 
• 99-02-5 3'-Chloroacetophenone 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 443777-09-1 1-(3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)ethanone 
• 33397-21-6 tris(4-methoxyphenyl)bismuth 
• 138313-22-1 3-acetylphenyl trifluoromethanesulfonate 
• 2142-63-4 1-(3-Bromophenyl)ethanone 
• 14452-30-3 3'-iodoacetophenone 
• 766-81-4 3-bromophenylacetylene 
• 121-71-1 3-Hydroxyacetophenone 
• 58297-34-0 3-acetylphenyl p-toluenesulfonate 
• 130952-94-2 (dichloro)(ethyl)(4-methoxyphenyl)silane 

Relevant articles and documents

Dual-Metal N-Heterocyclic Carbene Complex (M = Au and Pd)-Functionalized UiO-67 MOF for Alkyne Hydration-Suzuki Coupling Tandem Reaction

Metal N-heterocyclic carbene complexes (NHC-M) have been recognized as an important class of organometallic catalysts. Herein, we demonstrate that different NHC-M (M = Au and Pd) species can be simultaneously introduced into a single metal organic framework (MOF) by direct assembly of NHC-M-decorated ligands and metal ions under solvothermal conditions. The obtained UiO-67-Au/Pd-NHBC MOF with different organometallic NHC-M species can be a highly reusable dual catalyst to sequentially promote alkyne hydration-Suzuki coupling reaction. The potential utility of this strategy is highlighted by the preparation of many more new multicatalysts of this type for various organic transformations in a sequential way.

The Rational Design and Synthesis of Water-Soluble Thiourea Ligands for Recoverable Pd-Catalyzed Aerobic Aqueous Suzuki-Miyaura Reactions at Room Temperature

Eight precatalysts containing carboxylic-functionalized thiourea ligands are prepared and their activities and recyclability are evaluated in aerobic aqueous Suzuki-Miyaura reactions. A bulky monothiourea-Pd complex, functionalized with four carboxylic groups, shows the best activity and recyclability in the coupling of aryl bromides with arylboronic acids. The catalyst can be reused at least five times without any significant reduction in its catalytic activity. TEM analysis and the confirmed catalytic activity of the observed black precipitate reveal that Pd nanoparticles are formed during the reactions and are stabilized by the carboxylic-functionalized thiourea ligands.

Reusable Palladium N-Heterocyclic Tetracarbene for Aqueous Suzuki-Miyaura Cross-Coupling Reaction: Homogeneous Catalysis and Heterogeneous Recovery

A pH-responsive Pd(II) N-heterocyclic tetracarbene complex synthesized by a solvothermal method was reported. It can be a highly active reusable catalyst to homogeneously catalyze the Suzuki-Miyaura cross-coupling reaction in water and can be heterogeneously recovered by simply adjusting the pH value of the aqueous reaction media.

Picolinamide modified β-cyclodextrin/Pd (II) complex: Asupramolecular catalyst for Suzuki-Miyaura coupling of aryl, benzyl and allyl halides with arylboronic acids in water

Novel supramolecular catalysts for Suzuki-Miyaura coupling were prepared and characterized by NMR, FT-IR, TEM, XRD, TGA, and XPS. The resulting picolinamide-modified β-cyclodextrin/Pd(II) complex (Pd(II)@PCA-β-CD) showed very efficient catalytic activity for Suzuki-Miyaura coupling of aryl, benzyl, and allyl halides with arylboronic acids in an environmentally benign aqueous solution. Various organic halides including chlorides can produce good to excellent yields with phenyl-boronic acid and a catalytic amount of Pd(II)@PCA-β-CD. This hydro-soluble catalyst was capable of being reused for at least eight runs with only a slight loss of catalytic activity. A putative mechanism of the Pd(II)/Pd(IV) catalytic cycle was also explored and calculated by ab initio QM/MM methods.

Suzuki-Miyaura cross-coupling reaction of aryl chlorides with aryl boronic acids catalyzed by a palladium dichloride adduct of N-diphenylphosphanyl-2-aminopyridine

One palladium dichloride adduct of a phosphine-pyridine ligand N-diphenylphosphanyl-2-aminopyridine (L1) [(L1)PdCl2] (1) has been prepared and structurally characterized. Compound 1 can be used as an effective catalyst for the Suzuki-Miyaura cross-coupling reactions of unreactive aryl chlorides with aryl boronic acids, and worked much better than its mono- or bidentate phosphine ligands. The reactions with a wide scope of substrates proceeded to give desired products in good to excellent yields.

Palladium(II) Chloride Complexes of N,N′-Disubstituted Imidazole-2-thiones: Syntheses, Structures, and Catalytic Performances in Suzuki-Miyaura and Sonogashira Coupling Reactions

Reactions of PdCl2 with 2 equiv of N,N′-disubstituted-imidazole-2-thiones R1R2C3N2S (R1 = R2 = Me (1a), iPr (1b), Cy (1c), C6Me3H2 (1d); R1 = Me, R2 = Ph (1e)) under the different conditions afford five mononuclear complexes trans-[(R1R2C3N2S)2PdCl2] (R1 = R2 = Me (2a), iPr (2b), Cy (2c), C6Me3H2 (2d); R1 = Me, R2 = Ph (2e)) and five binuclear Pd(II) complexes [(PdCl2){μ-(R1R2C3N2S)}]2 (R1 = R2 = Me (3a), iPr (3b), Cy (3c), C6Me3H2 (3d); R1 = Me, R2 = Ph (3e)), respectively. Complexes 2a-2e are easily converted into the corresponding 3a-3e by adding equimolar PdCl2 in refluxing MeOH, while the reverse reaction is achieved at room temperature by addition of 2 equiv of 1a-1e. In 2b, 2d, and 2e, each Pd(II) holds a distorted square planar geometry completed by two trans Cl atoms and two trans S atoms. Complexes 3a-3e have a dimeric [Pd2S2] structure in which two {PdCl2} units are interlinked by two N,N′-disubstituted-imidazole-2-thiones. Each Pd(II) adopts a distorted square planar geometry accomplished by two cis Cl atoms and two cis bridging S atoms. Among them, complex 3d has the two largest C6Me3H2 groups on the 2 and 5 positions of imidazole-2-thione, the longest Pd-μ-S bond, the largest S-Pd-S angle, and displays the highest catalytic activity toward Suzuki-Miyaura and copper-free Sonogashira cross-coupling reactions, which are confirmed by density functional theory calculations. The results provide an interesting insight into the introduction of various substituent groups into the periphery ligands of coordination complex-based catalysts, which could tune their geometric structures to acquire the best catalytic activity toward organic reactions.

Dimeric ortho-palladated complex of 2,3-dimethoxybenzaldehyde oxime catalyzed Suzuki-Miyaura cross-coupling reaction under microwave irradiation

Abstract The catalytic activity of dimeric [Pd{C6H2(-CH=NOH)-(OMe)2-2,3}(μ-Cl)]2 complex as an efficient, air, and moisture-tolerant catalyst was investigated in Suzuki cross-coupling reactions of various aryl halides. The combination of homogenous metal catalyst, microwave irradiation, and microwave-active polar solvents gave high yields of substituted biaryl products in short reaction times.

Versatile palladium(II)-catalyzed Suzuki-Miyaura coupling in ethanol with a novel, stabilizing ligand

Suzuki-Miyaura coupling reactions of arylboronic acids with aryl bromides were mediated by PdCl2 and bdppmapy (N,N-bis-(diphenylphosphanylmethyl)-2-aminopyridine) that both stabilizes and solubilizes the catalyst in predominantly ethanol as a solvent. Excellent yields for a wide variety of substrates were obtained under relatively mild conditions in this 'green' solvent.

Suzuki-Miyaura coupling of aryl sulfonates with arylboronic acids using a morpholine-Pd(OAc)2 catalyst system

We report a new catalyst system, a morpholine-Pd(OAc)2 complex, for Suzuki-Miyaura coupling of aryl tosylates or mesylates with arylboronic acids to give biaryl compounds. The morpholine-Pd(OAc)2 catalyst system is proposed to be a precursor of the catalytically active species in the coupling reaction. Aryl chlorides and aryl triflates can also be used in this coupling reaction. Altogether, 22 biaryl compounds were obtained using this catalyst system. We report a new catalyst system, a morpholine-Pd(OAc) 2 complex, for Suzuki-Miyaura coupling of aryl tosylates or mesylates with arylboronic acids to give biaryl compounds. The morpholine-Pd(OAc) 2 catalyst system is proposed to be a precursor of the catalytically active species in the coupling reaction. Copyright

Facile-prepared sulfonated water-soluble PEPPSI-Pd-NHC catalysts for aerobic aqueous Suzuki-Miyaura cross-coupling reactions

Four sulfonated water-soluble PEPPSI-Pd-NHC complexes (2a-2d) are prepared in a straightforward two-step synthesis. Their activities have been examined in Suzuki-Miyaura cross-coupling reactions in water under air. Complex 2d, bearing a 2,6-diisopropylphenyl substituent, shows the best catalytic activity and a variety of aryl bromides with a catalyst loading of 0.1 mol% can be efficiently activated even at room temperature. The catalyst is recyclable and can be employed in at least four consecutive runs without significant loss in performance. Furthermore, TEM analysis, kinetic studies and mercury poisoning experiments indicate that Pd nanoparticles are formed during the reactions.