6460-91-9

Usage

Structure

A biphenyl derivative with a methoxy group and a nitro group

Appearance

Pale yellow solid

Melting point

121-122°C

Uses

a. Organic synthesis
b. Building block for various organic compounds
c. Reagent in chemical reactions
d. Precursor in the synthesis of pharmaceuticals, dyes, and fine chemicals

Potential applications

a. Medicine
b. Biochemistry

Biological activities

May have properties that contribute to its potential use in medicine and biochemistry
These properties and specific content are based on the information provided about 1,1'-Biphenyl, 2-methoxy-4'-nitro-.

Upstream product

• 16186-97-3 α-(4-nitrophenylazo)triphenylmethane 
• 100-66-3 methoxybenzene 
• 456-27-9 4-nitrobenzenediazonium tetrafluoroborate 
• 5720-06-9 2-Methoxyphenylboronic acid 
• 100-01-6 4-nitro-aniline 
• 586-78-7 para-nitrophenyl bromide 
• 636-98-6 p-nitrobenzene iodide 
• 100-00-5 4-chlorobenzonitrile 

Downstream Products

• 263901-48-0 2'-Methoxy-biphenyl-4-ylamine 
• 666726-32-5 6-(2-methoxybiphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline 
• 666726-33-6 4-bromomethyl-6-(2-methoxybiphenyl)-2,2,-dimethyl-1,2-dihydroquinoline 
• 39117-68-5 2,4,6-trimethyl-4'-nitro-1,1'-biphenyl 

Relevant academic research and scientific papers

Competent synthesis of biaryl analogs via asymmetric Suzuki–Miyaura cross-coupling for the development of anti-inflammatory and analgesic agents

Based on the core structure of diflunisal drug, herein, we report a resembling series of biaryl analogs (3a–j) containing halogens, nitro, and methoxy substituents. They were designed and synthesized via a Suzuki–Miyaura cross-coupling reaction using Pd (OH)2 as a catalyst at a temperature of 65?°C with an intent to obtain improved and safer anti-inflammatory and analgesic agents. Suzuki–Miyaura transformation is the most significant among the cross-coupling reactions since its practical advantages include the commercially available low toxic reagents, mild reaction conditions, and functional group compatibility. On the other hand, a few conditions can be used to cross-couple aryl boronic acids or esters with aryl halides, especially 2-benzyl halides. Because of this, a novel Suzuki–Miyaura protocol is investigated that facilitates the selective conversion of halo aromatics, with an emphasis on the reaction to convert substituted bromobenzene to conjugated biphenyls. Finally, the obtained biaryl analogs (3a–j) were tested for in vitro and in vivo anti-inflammatory and analgesic applications. The results showed that compound 3b performed better than the standard drug with IC50 values comparable to that of the standard drug for COX-1 and COX-2 inhibition. Finally, molecular docking tests for the effective compound were carried out.

Pyrazole-Mediated C-H Functionalization of Arene and Heteroarenes for Aryl-(Hetero)aryl Cross-Coupling Reactions

Herein we introduce a transition-metal-free protocol that involves a commercially available, inexpensive pyrazole molecule to conduct C-C cross-coupling reactions at room temperature via a radical pathway. Using this method, an aryldiazonium salt has been coupled to a wide range of arenes and heteroarenes including benzene, mesitylene, thiophene, furan, benzoxazole to result the corresponding biaryl products. The full reaction mechanism is elucidated along with the crystallographic probation of an active initiator species. A potassium-stabilized deprotonated pyrazole steers single-electron transfer to the substrate and behaves as an initiator for the reaction.

Sublimable bis(β-iminoenolate)palladium(II) complexes and their application as catalysts in Suzuki-Miyaura reactions

The Pd(II) complexes strongly chelated by two β-iminoenolate ligands were easily synthesized in only two steps, and purified based on their sublimable and highly stable property. The Pd(II) complexes anchored on a silica surface showed good catalytic activity in Suzuki-Miyaura reactions (up to 99% yield with 0.05 mol% catalyst). They tolerated a wide range of temperature (rt～110 °C) and various solvents, and could be reused multiple times after simple recovering process.

Amphipathic monolith-supported palladium catalysts for chemoselective hydrogenation and cross-coupling reactions

A palladium catalyst immobilized on an amphipathic and monolithic polystyrene-divinylbenzene polymer bearing strongly acidic cation exchange functions (sulfonic acid moieties) (Pd/CM) was developed. It was used as a catalyst for hydrogenation and ligand-free cross-coupling reactions, such as the Suzuki-Miyaura, Mizoroki-Heck, and copper- and amine-free Sonogashira-type reactions, together with a palladium catalyst supported on monolithic polymer (Pd/AM) bearing basic anion exchange functions (ammonium salt moieties), which has been in practical use for the decomposition of hydrogen peroxide produced as a byproduct during the manufacture of ultrapure water. While the Pd/CM was highly active as a catalyst for the hydrogenation and a variety of reducible functional groups could be reduced, the use of Pd/AM led to a unique chemoselective hydrogenation. Aromatic carbonyl groups were tolerant under the Pd/AM-catalyzed hydrogenation conditions, although benzyl esters, benzyl ethers, and N-Cbz groups could be smoothly hydrocracked. The cross-coupling reactions readily proceeded using either catalyst. The palladium leaching from the Pd/CM into the reaction media was never observed during the Sonogashira-type reaction, which was hardly achieved by other palladium-supported heterogeneous catalysts due to the good affinity of the palladium species with alkynes.

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.

Dual gold photoredox C(sp2)-C(sp2) cross couplings-development and mechanistic studies

A dual visible light photoredox and gold-catalysed C(sp2)-C(sp2) cross coupling is described. The success of this mild, oxidant- and base-free cross coupling is highly dependent on the amount of water added. Mechanistic studies show two distinct pathways depending on the gold catalyst employed: transmetallation of the arylboronic acid with gold(i) occurs prior to oxidation of gold(i) to gold(iii) using cationic gold(i) catalysts, whereas oxidation of gold(i) to gold(iii) precedes transmetallation using neutral gold(i) catalysts.

Palladium on carbon-catalyzed solvent-free and solid-phase hydrogenation and Suzuki-Miyaura reaction

The solvent-free and solid-phase hydrogenation of various reducible functionalities was efficiently catalyzed by heterogeneous palladium on carbon (Pd/C) under ambient hydrogen pressure and temperature. The Pd/C-catalyzed Suzuki-Miyaura coupling reaction between solid aryl bromides and solid arylboronic acids to generate the corresponding solid biaryls was also achieved under the totally solid-phase conditions.

In situ formation of N,O-bidentate ligand via the hydrogen bond for highly efficient Suzuki reaction of aryl chlorides

A highly efficient protocol for the Pd(OAc)2-catalyzed aerobic Suzuki reaction of aryl chlorides is reported, which is proposed to be promoted by the N,O-bidentate ligand formed in situ via the hydrogen bond of solvents.

Direct coupling of arenes and iodoarenes catalyzed by a rhodium complex with a strongly π-accepting phosphite ligand

A new rhodium-based catalytic system for the direct C-H coupling of arenes and iodoarenes that shows high activity with reasonably broad scope was developed. Under the catalytic influence of RhCl(CO){P[OCH(CF3)2]3}2 and Ag2CO3, the direct C-H arylation of heteroarenes and arenes took place with iodoarenes to afford a range of biaryls in good to excellent yields with high regioselectivity. Thiophenes, furans, pyrroles, indoles, and alkoxybenzenes are applicable to this arylation protocol.