39858-88-3

Basic information

• Product Name: 2,2'-Bipyridine, 6,6'-dimethoxy-
• CAS NO: 39858-88-3
• Molecular Formula: C12H12N2O2
• Molecular Weight: 216.239
• Mol File: 39858-88-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2,2'-Bipyridine, 6,6'-dimethoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-Bipyridine, 6,6'-dimethoxy-(39858-88-3)
• EPA Substance Registry System: 2,2'-Bipyridine, 6,6'-dimethoxy-(39858-88-3)

Safety Data

• Hazardous Substances Data: 39858-88-3(Hazardous Substances Data)

Usage

Chemical composition

Contains two pyridine rings and two methoxy groups on each ring.

Common use

As a ligand in coordination chemistry.

Purpose

Binds to metal ions to form coordination complexes.

Potential applications

Catalysis, material science, and medicinal chemistry.

Upstream product

• 109-04-6 2-bromo-pyridine 
• 40473-07-2 6-bromo-2-methoxypyridine 
• 34160-40-2 6-bromo-2-pyridinecarbaldehyde 
• 696-62-8 para-iodoanisole 
• 2845-89-8 1-chloro-3-methoxy-benzene 
• 142929-26-8 4-Methoxy-3-(trimethylstannyl)pyridin 
• 17228-64-7 6-chloro-2-methoxypyridine 

Downstream Products

• 103505-54-0 1H,1’H-[2,2’]bipyridyl-6,6’-dione 
• 103505-54-0 6,6′‐dihydroxyl‐2,2′‐bipyridine 

Relevant articles and documents

Zirconium-redox-shuttled cross-electrophile coupling of aromatic and heteroaromatic halides

Transition metal-catalyzed cross-electrophile coupling (XEC) is a powerful tool for forging C(sp2)–C(sp2) bonds in biaryl molecules from abundant aromatic halides. While the synthesis of unsymmetrical biaryl compounds through multimetallic XEC is of high synthetic value, the selective XEC of two heteroaromatic halides remains elusive and challenging. Herein, we report a homogeneous XEC method, which relies on a zirconaaziridine complex as a shuttle for dual palladium-catalyzed processes. The zirconaaziridine-mediated palladium (ZAPd)-catalyzed reaction shows excellent compatibility with various functional groups and diverse heteroaromatic scaffolds. In accord with density functional theory (DFT) calculations, a redox transmetallation between the oxidative addition product and the zirconaaziridine is proposed as the crucial elementary step. Thus, cross-coupling selectivity using a single transition metal catalyst is controlled by the relative rate of oxidative addition of Pd(0) into the aromatic halide. Overall, the concept of a combined reducing and transmetallating agent offers opportunities for the development of transition metal reductive coupling catalysis.

Tetrabutylammonium 2-pyridyltriolborate salts for Suzuki-Miyaura cross-coupling reactions with aryl chlorides

Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of tetrabutylammonium 2-pyridyltriolborate salts with various aryl (heteroaryl) chlorides can produce the corresponding desired coupling products with good to excellent yields. These tetrabutylammonium salts are more reactive than the corresponding lithium salts. The coupling reactions with aryl chlorides progressed in the presence of PdCl2dcpp (3 mol %) and CuI/MeNHCH 2CH2OH (20 mol %) in anhydrous DMF without bases.

ACTIVATION OF REDUCING AGENTS. SODIUM HYDRIDE CONTAINING COMPLEX REDUCING AGENTS 23. SYMMETRICAL COUPLING OF NITROGEN-CONTAINING HETEROCYCLIC HALIDES

The preparation of NiCRA (NaH-tBuONa-Ni(OAc)2) in the presence of PPh3 leads to a reagent (termed NiCRA-PPh3) which is shown to be one of the most efficient Ni containing reagents reported so far for the homocoupling of heteroaromatic halides.