26844-80-4

Usage

Uses

Used in Coordination Chemistry:
5-METHYL-[2,3']-BIPYRIDINE is used as a ligand for forming coordination complexes with various metal ions. Its ability to chelate metals contributes to its utility in creating stable complexes that are valuable in numerous chemical and industrial processes.
Used in Synthesis of Other Chemical Compounds:
As a precursor, 5-METHYL-[2,3']-BIPYRIDINE is utilized in the synthesis of other chemical compounds. Its unique structure allows it to be a key component in the creation of new molecules with specific properties for various applications in the chemical industry.
Used in Research and Development:
5-METHYL-[2,3']-BIPYRIDINE is also employed in research and development settings, where its properties and reactivity are studied to understand its potential uses and to develop new methodologies in organic synthesis and coordination chemistry.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, given its role in coordination chemistry, 5-METHYL-[2,3']-BIPYRIDINE could potentially be used in the pharmaceutical industry as a component in the development of metal-based drugs or as a part of drug delivery systems that require metal coordination for their function.
Used in Analytical Chemistry:
In analytical chemistry, 5-METHYL-[2,3']-BIPYRIDINE may be used for the detection and analysis of metal ions, given its ability to form complexes with these ions, which can be detected and quantified using various analytical techniques.

Upstream product

• 626-55-1 3-Bromopyridine 
• 108-99-6 3-Methylpyridine 
• 851367-90-3 C₁₁H₁₂Cl₂N₂ 
• 3510-66-5 2-Bromo-5-methylpyridine 
• 329214-79-1 3-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 
• 1692-25-7 3-pyridylboronic acid 

Relevant academic research and scientific papers

Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates

Here we describe the discovery of a new class of C-H borylation catalysts and their use for regioselective C-H borylation of aromatic, heteroaromatic, and aliphatic systems. The new catalysts have Ir-C(thienyl) or Ir-C(furyl) anionic ligands instead of the diamine-type neutral chelating ligands used in the standard C-H borylation conditions. It is reported that the employment of these newly discovered catalysts show excellent reactivity and ortho-selectivity for diverse classes of aromatic substrates with high isolated yields. Moreover, the catalysts proved to be efficient for a wide number of aliphatic substrates for selective C(sp3)-H bond borylations. Heterocyclic molecules are selectively borylated using the inherently elevated reactivity of the C-H bonds. A number of late-stage C-H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp2)-H and C(sp3)-H borylations enabling the method more general. Preliminary mechanistic studies suggest that the active catalytic intermediate is the Ir(bis)boryl complex, and the attached ligand acts as bidentate ligand. Collectively, this study underlines the discovery of new class of C-H borylation catalysts that should find wide application in the context of C-H functionalization chemistry.

Synthesis and spectroscopic comparison of the eight methyl-2,3′-bipyridyls and identification of a hoplonemertine alkaloid as 3-methyl-2,3′-bipyridyl

The pyridyl ring is frequently found in natural products and drugs. While bipyridyls have served as useful scaffolds for development of industrial and pesticidal chemicals, their biological properties are still not well understood. Only 2,3--bipyridyl, of the six isomeric bipyridyls, has been reported as a natural product in tobacco plants and in a hoplonemertine marine worm, Amphiporus angulatus (Aa), which uses its pyridyl alkaloid-rich venom to paralyze its crustacean prey and chemically defend itself against predators. Here we report for the first time the synthesis and spectroscopic properties of all eight possible methyl 2,3′-bipyridyl isomers and use this data to identify a trace alkaloidal constituent of Aa as 3-methyl-2,3′-bipyridyl. This is only the second reported instance of a methyl-bipyridyl being found as a natural product, the first being the tobacco alkaloid 5-methyl-2,3′-bipyridyl.

5-Substituted, 6-substituted, and unsubstituted 3-heteroaromatic pyridine analogues of nicotine as selective inhibitors of cytochrome P-450 2A6

A series of 5- and 6-substituted and unsubstituted 3-heteroaromatic analogues of nicotine were synthesized in an effort to delineate the structural requirements for selectively inhibiting human cytochrome P-450 (CYP) 2A6, the major nicotine metabolizing enzyme. Thiophene, substituted thiophene, furan, substituted furan, imidazole, substituted imidazole, pyridine, substituted pyridine, thiazole, and quinoline moieties were used to replace the N-methylpyrrolidine ring of nicotine. Bromo and methyl groups were introduced at the 5-position of the pyridine ring and fluoro, chloro, and methoxy groups were placed at the 6-position of the pyridine ring in order to explore the structure-activity relationship (SAR) of inhibition of CYP2A6. The inhibitory activity of the most potent CYP2A6 inhibitors on the functional activity of human cytochrome P450s 3A4, 2E1, 2B6, 2C9, 2C19, and 2D6 was also examined to determine inhibitor selectivity. We identified 36 compounds that were more potent than nicotine at inhibition of coumarin 7-hydroxylase (CYP2A6) activity. We also found a number of compounds to be highly selective for the inhibition of human CYP2A6 versus the other human CYPs examined.

SYNTHETIC COMPOUNDS AND DERIVATIVES AS MODULATORS OF SMOKING OR NICOTINE INGESTION AND LUNG CANCER

Disclosed are nicotine-related compounds that selectively inhibit cytochrome P-450 2A6 (CYP2A6), selectively inhibit cytochrome P-450 2A13 (CYP2A13), and/or selectively modulate a nicotinic acetylcholine receptor (nAChR). Also disclosed are pharmaceutical compositions comprising a compound of the invention, as well as methods of using the pharmaceutical compositions for treating or preventing a disease or disorder associated with nicotine-ingestion, or a disease or disorder amenable to treatment by selective modulation of nAChRs.

Straightforward access to methyl-polyheterocycles from direct para-lithiation of 3-picoline

Various heterocycles have been introduced on the 3-picoline nucleus via a regioselective BuLi-Me2N(CH2)2OLi (BuLi-LiDMAE) mediated para-lithiation. Useful methyl-polyheterocycles were efficiently prepared by a one-pot lith