20854-60-8

Usage

Uses

Used in Organic Synthesis:
(4'-METHOXYBIPHENYL-4-YL)-METHANOL is used as a building block for the synthesis of various organic compounds due to its ability to react with a wide range of functional groups and its compatibility with different chemical environments.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (4'-METHOXYBIPHENYL-4-YL)-METHANOL is used as a key intermediate in the development of pharmaceuticals. Its hydrophobic and hydrophilic properties allow it to interact with biological targets, making it a promising candidate for the creation of new drugs.
Used in Drug Discovery and Development:
(4'-METHOXYBIPHENYL-4-YL)-METHANOL is utilized in drug discovery and development processes for its potential pharmacological activities. Its unique structure and reactivity make it a valuable tool for exploring new therapeutic agents and advancing the understanding of molecular interactions in biological systems.

Upstream product

• 725-14-4 4'-methoxy-biphenyl-4-carboxylic acid 
• 5720-07-0 4-methoxyphenylboronic acid 
• 873-76-7 para-Chlorobenzyl alcohol 
• 18282-51-4 4-iodo-benzyl alcohol 
• 33397-21-6 tris(4-methoxyphenyl)bismuth 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 99768-12-4 4-methoxycarbonylphenylboronic acid 
• 873-75-6 4-bromobenzenemethanol 
• 623-12-1 4-chloromethoxybenzene 
• 59016-93-2 p-hydroxymethylphenylboronic acid 
• 459-56-3 4-fluorobenzylic alcohol 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 56116-76-8 1-(4'-methoxy[1,1'-biphenyl]-4-yl)propan-1-one 
• 613-37-6 4-methoxylbiphenyl 

Downstream Products

• 53040-92-9 4-(4-tolyl)anisole 

Relevant academic research and scientific papers

Single monodentate N-donor ligands versus multi-ligand analogues in Pd(II)-catalysed C–C coupling at reduced temperatures

Deployment of reduced operational temperatures is industrially beneficial and use of the highly efficient, phosphine-based precatalysts is limited by their high costs and inaccessible preparation procedures. In order to study of the influence of coordination environments on catalyst reactivities at reduced temperatures, design of palladium(II) complexes bearing single monodentate N-donor ligands was considered necessary. Consequently, dichloridopalladium(II) complexes of 2-(thiophen-2-yl)-1H-imidazole ligands (1–8), 2,4,5-triphenyloxazole (9) and 2-(1H-imidazol-2-yl)pyridine (10) have been prepared, structurally characterized and studied as N-stabilized precatalysts. Ligand donor strengths were spectroscopically estimated by protonation-deprotonation equilibria. The palladium(II) complexes were obtained in three coordination environments; (i) the mono-ligand complexes bearing trans-solvent co-ligands (PdL.acn and PdL.dmf), (ii) the chlorido-bridged dimers μ-(PdL)2 and (iii) the trans-bis-ligand PdL2 complexes. Considering ambient temperature operations, the catalysis outcomes obtained for the monodentate mono-ligand coordination designs represent an improvement in terms of temperature and reaction time relative to previously reported N-stabilized palladium precatalysts. The mono-ligand pre-catalysts efficiently generate living active palladium species from 40 °C while a trans-bis-ligand phosphine-based pre-catalyst analogue PdI2(PPh3)2 displayed no yield under the same temperature conditions. Trans-bis-ligand coordination is observed to utterly hinders catalyst efficiencies at the studied temperatures and preformed mono-ligand complexes of mono-dentate N-donors provided positive ligand effects while in situ catalyst generation failed. Therefore, the use of multiple ligand equivalents should be discouraged.

Biphenyl derivatives containing trimethylsilyl benzyl ether or oxime groups as probes for NO2 detection

Four probes based in the use of a biphenyl moiety and functionalized with trimethylsilyl benzyl ether (P1 and P3) and oxime (P2 and P4) groups have been prepared and tested as optical probes for the detection of NO2. Reaction of NO2 with acetonitrile solutions of P2-P4 resulted in the formation of aldehydes 7 and 8 with a concomitant redshift of the absorption bands. Probe P2 displayed a bathochromic shift of 45 nm upon reaction with NO2 and was able to detect this poisonous gas at concentrations as low as 0.02 ppm. P2 was highly selective against NO2 and other gases (i.e. NO, CO2, H2S, SO2) and vapours of organic solvents (i.e. acetone, hexane, chloroform, acetonitrile or toluene) had no effect in the optical properties of the probe.

Bimetallic docked covalent organic frameworks with high catalytic performance towards coupling/oxidation cascade reactions

Covalent organic frameworks (COFs) are an emerging class of crystalline porous polymers that make these materials suitable for use as excellent scaffold in heterogeneous catalysis. Here we synthesize a layered two-dimensional (2D) COF (TADP-COF) through the condensation reaction between four-branched 5,10,15,20-tetrakis(4-aminophenyl)porphyrin (TAPP) and linear 2,5-dihydroxyterephthalaldehyde (Dha) and 1,4-phthalaldehyde (PA) building blocks. Porphyrin units, imine and hydroxyl groups together with imines can provide wide coordination sites for metal docking. Using a programmed synthetic procedure, Cu(ii) ions first coordinated with the imine groups in conjunction with their adjacent hydroxyl groups, and porphyrin units and subsequently added Pd(ii) ions occupied the remaining imine sites in the space between adjacent COF layers. The bimetallic Pd(ii)/Cu(ii)@TADP-COF showed high catalytic activity in a one-pot coupling/oxidation cascade reaction in water. The high surface area, one-dimensional (1D) open channel structure and predesigned catalytic active sites of this material make it ideal candidate for use as heterogeneous catalyst in a wide range of catalytic reactions.

New Bidentate N-Sulfonyl-Substituted Aromatic Amines as Chelate Ligand Backbones: Pd Catalyst Generation in C-C Coupling via in Situ and Precatalyst Modes

A series of six new, bidentate ligands based on N-(2-(R-sulfonamido)benzyl)R-sulfonamide have been isolated as dianionic or monoanionic chelators via condensation of 2-(aminomethyl)aniline with sulfonyl chloride reagents; R = methyl (1 and 1′), tolyl (2 and 2′), 2,4,6-Trimethylphenyl (3), or 2,4,6-Triisopropylphenyl (4). Complexes of ligands 2-4 reacted at room temperature with palladium(ii) acetate in the presence of various monodentate N-donor co-ligands to form complexes Pd2(2dmap), Pd2′(OAc.py), Pd3(2acn), Pd3(2py), Pd4(2acn), and Pd4(2py), which were structurally confirmed by three X-ray crystal analyses. Results of catalysis studies in water showed high turnover frequencies and yields of up to 98 % within 10 min and at 0.2 mol-% palladium catalyst loading. Relative to ligand-free catalysis in the presence of only Pd(OAc)2, the ligand-supported palladium species clearly possess positive catalytic advantage. Furthermore, Suzuki coupling efficiencies by 1: 1 'Pd(OAc)2 + ligand' yielded notably better outcomes than for the 1: 2 'Pd(OAc)2 + ligand' in situ catalyst generation, which reveals that coordinative saturation is undesirable. The size of the complementing monodentate co-ligand was observed to influence the catalytic efficiency such that bulkier co-ligands consistently yielded improved turnover frequency values, which leads to the conclusion that steric repulsion between the synthesised ligands and the bulkier co-ligands aided the generation of vacant coordination sites for the more active complexes. Moderate Heck coupling activity was recorded for the complexes and better activities appear to correlate with moderate bulkiness of ligand 3.

Pd-catalyzed atom-efficient cross-coupling of triarylbismuth reagents with protecting group-free iodophenylmethanols: Synthesis of biarylmethanols

An atom-efficient procedure for the synthesis of functionalized biarylmethanols via the Pd-catalyzed cross-coupling reactions of differently functionalized iodophenylmethanols and triarylbismuth reagents is described. This protecting group-free direct couplings of 2-, 3- or 4-iodophenylmethanols with triarylbismuth reagents afforded biarylmethanols in good to high yields.

N-donor-stabilized Pd(II) species supported by sulphonamide-azo ligands: Ligand architecture, solvent co-ligands, C–C coupling

In this report, a series of synthetically affordable phosphine-free ligands (L1 – L4) of the form RSO2–NH–Ph–N[dbnd]N–Ph–NH–SO2R were prepared and examined as organic ligands for stabilizing palladium active centers; R = methyl, tolyl or triiso-propylphenyl. Palladium complexes, which were obtained in varying coordination environments as well as with varying complementary co-ligands (water, acetonitrile or pyridine), have been subjected to Suzuki and Heck coupling experiments in order to study molecular level ligand effects on preferred catalyst settings. The appreciable coupling activities for Suzuki and Heck coupling with functional group tolerance were recorded for palladium species generated from the chelate ligands. Results show that, despite the tridentate chelation characteristics of these azo-benzene ligands, the introduction of bulky units at the sulfonyl groups enabled generation of active palladium species with high turnover frequencies; e.g. 5040 h?1 (84% yield) within 5 min at 0.2 mol % loading of Pd.L2.py in only water as solvent. A correlation between catalytic efficiencies and the bulkiness of the coordinated co-ligand was obtained. However, while Suzuki coupling activity increased with increase in co-ligand sizes of the preformed complexes (i.e. water acetonitrile pyridine), the pyridyl co-ligand turned out to be very unfavourable for Heck coupling where the acetonitrile-complemented complexes possessed the higher activities. Therefore, it could be concluded that the best catalyst setting for Suzuki coupling may not be the best for Heck reaction.

Importance of monodentate mono-ligand designs in developing N-stabilized Pd catalysts for efficient ambient temperature C[sbnd]C coupling: Donor strengths and steric features

Unfriendly temperature profiles and costs of carbon coupling catalysis, which pose challenge to both synthetic organic chemists as well as industrial applicability, motivated our design of new monodentate N-donors as support ligands for the purpose of constructing ambient temperature precatalysts that are molecularly close to the hypothetical active forms. Therefore, a series of sterically varied monodentate N-donor imidazoles (1–7) and oxazoles (8–9) have been synthesized and their N-donor strengths, which were estimated as pKas, are systematically varied from 0.9 to 8.5 by substituent variations. Eleven target mono-ligand complexes (1-PdCl2MeCN – 9-PdCl2MeCN, 6-PdCl2PhCN and 7-PdCl2PhCN) and six trans-bis-ligand complexes (12-PdCl2, 22-PdCl2, 32-PdCl2, 62-PdCl2, 12-Pd(OAc)2 and 22-Pd(OAc)2) were isolated and catalytically studied along with PdI2(PPh3)2. Results of coupling reactions, which were conducted both via in situ ‘Pd(II) salt + ligand’ approach and by use of the precatalysts, show that the mono-ligand precatalyst designs (1-PdCl2MeCN – 9-PdCl2MeCN, 6-PdCl2PhCN and 7-PdCl2PhCN) represent a true catalyst improvement initiative among the phosphine-free catalyst community; i.e. yields approaching 100% (TOF ≈ 2000) at 0.2 mol % catalyst loading, 45 °C and within 15 min. On the other hand, the complexes with trans-bis-ligand coordination were inactive at ambient temperatures. Therefore, it was concluded that coordinative saturation, which results from implementing two or more ligand equivalents or use of polydentate ligands on palladium, should be strongly discouraged. Such saturation necessitates the undesirable and avoidable high temperature necessities, long reflux durations and needlessly high catalyst loadings. Correlation between catalyst activity and donor strengths or steric properties were analysed leading to important conclusions. The catalyst design also supported coupling of activated aryl chlorides from 60 °C while Heck coupling activities were observed only at the early minutes of reactions.

N-donor 2-(Sulfonamido)benzamide ligands, their palladium(II) coordination species and C–C coupling catalysis efficiencies

A series of synthetically accessible ligands based on new 2-(R-sulfonamido)benzamide have been prepared (R = methyl for H3M; R = 4-toly for H3T and T2CN; R = 2,4,6-triisopropylphenyl for H3iP and HiPCN). The R-substituents were selected to vary in sizes. Allowing ligand H3iP and palladium acetate to stand in solvent leads to self-assembly of the well-defined solvent- and stoichiometry-controlled tetranuclear or hexanuclear coordination macromolecules Pd4(iP)2 and (PdHiP)6, which were analysed by X-ray crystallography. It was observed that palladium active species for Suzuki coupling catalysis could be stabilized by these simple and synthetically assessable N-donor ligands as revealed by turnover frequencies reaching 5500 h?1. Electronic features of these N-donors appear to be more important than the steric properties.

Azole-based non-peptidomimetic plasmepsin inhibitors

The spread of drug-resistant malaria parasites urges the search for new antimalarial drugs. Malarial aspartic proteases – plasmepsins (Plms) – are differentially expressed in multiple stages of the Plasmodium parasite's lifecycle and are considered as attractive drug targets. We report the development of novel azole-based non-peptidomimetic plasmepsin inhibitors that have been designed by bioisosteric substitution of the amide moiety in the Actelion amino-piperazine inhibitors. The best triazole-based inhibitors show submicromolar potency toward Plm II, which is comparable to that of the parent Actelion compounds. The new inhibitors can be used as a starting point for the development of a resistance-free antimalarial drug targeting the non-digestive Plm IX or X, which are essential for the malaria parasite life cycle.

SUBSTITUTED AMINOALKYLAZOLES AS MALARIAL ASPARTIC PROTEASE INHIBITORS

The present invention relates to novel aminoalkylazoles acting as inhibitors of malarial protease plasmepsin II. These can be used as medicines or as constituent of medicines for the treatment of malaria infection.