659742-21-9

Basic information

• Product Name: 6-Methylpyridine-3-boronic Acid
• Synonyms: 2-METHYL-5-PYRIDINYLBORONIC ACID;2-METHYLPYRIDINE-5-BORONIC ACID;(6-METHYLPYRIDIN-3-YL)BORONIC ACID;6-METHYLPYRIDINE-3-BORONIC ACID;Boronicacid,(6-methyl-3-pyridinyl);Boronic acid, (6-methyl-3-pyridinyl)- (9CI);6-Methylpyridine-3-Boronic;2-Methylpyridin-5-ylboronic acid
• CAS NO: 659742-21-9
• Molecular Formula: C₆H₈BNO₂
• Molecular Weight: 136.94
• EINECS: 1308068-626-2
• Product Categories: PYRIDINE;blocks;BoronicAcids;Pyridines;Boronate Ester;Boronic Acid;Potassium Trifluoroborate
• Mol File: 659742-21-9.mol

Chemical Properties

• Boiling Point: 294.7 °C at 760 mmHg
• Flash Point: 132 °C
• Appearance: White to pale brown/Powder
• Density: 1.18 g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.528
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.27±0.10(Predicted)
• CAS DataBase Reference: 6-Methylpyridine-3-boronic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Methylpyridine-3-boronic Acid(659742-21-9)
• EPA Substance Registry System: 6-Methylpyridine-3-boronic Acid(659742-21-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 659742-21-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-Methylpyridine-3-boronic Acid is used as a key intermediate in the synthesis of biologically active compounds, such as phosphoinositide-3-kinases (PI3K) and c-jun N-terminal kinase (JNK) inhibitors. These inhibitors play a crucial role in the development of drugs targeting various diseases, including cancer and inflammatory conditions, by modulating specific signaling pathways.
Used in Organic Synthesis:
6-Methylpyridine-3-boronic Acid is used as a reagent in the Suzuki reaction, a widely employed cross-coupling reaction in organic chemistry. This reaction allows for the formation of carbon-carbon bonds between an aryl or vinyl halide and an organoboron compound, facilitating the synthesis of complex organic molecules with potential applications in materials science, pharmaceuticals, and agrochemicals.

InChI:InChI=1/C6H8BNO2/c1-5-2-3-6(4-8-5)7(9)10/h2-4,9-10H,1H3

Upstream product

• 1121-78-4 5-Hydroxy-2-methylpyridine 
• 3430-13-5 5-bromo-2-methylpyridine 
• 5419-55-6 Triisopropyl borate 
• 111770-91-3 (6-methylpyridin-3-yl)trifluoromethanesulfonate 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 638219-10-0 6-(1-methanesulfonyl-1-methyl-ethyl)-8-[3-(6-methyl-pyridin-3-yl)-phenyl]-quinoline 
• 849757-67-1 3-chloro-2-(6-methylpyridin-3-yl)pyridine 
• 1032314-38-7 N-(2-methyl-5-nitrophenyl)-4-(6-methyl-3-pyridyl)-2-pyrimidineamine 
• 1032314-85-4 4-[(4-methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(6-methylpyridin-3-yl)-2-pyrimidinyl]amino]-phenyl]benzamide 
• 1383798-69-3 (+/-)-3-(6-(3-methyl-1-(4-(6-methylpyridin-3-yl)phenyl)butylamino)nicotinamido)propanoic acid 
• 1359945-84-8 C₂₄H₁₉F₆N₃O₃ 
• 109-06-8 α-picoline 
• 21203-68-9 2-methyl-5-nitropyridine 
• 18699-87-1 2-methyl-3-nitropyridine 
• 57927-99-8 2-methyl-3,5-dinitropyridine 
• 1214909-54-2 C₂₄H₂₃F₂N₅O 
• 1350643-75-2 8-(6-methylpyridin-3-yl)-2-phenyl-3-((S)-l-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-ylamino)ethyl)isoquinolin-1(2H)-one 

Relevant articles and documents

A novel inhibitor of inducible NOS dimerization protects against cytokine-induced rat beta cell dysfunction

Background and Purpose: Beta cell apoptosis is a major feature of type 1 diabetes, and pro-inflammatory cytokines are key drivers of the deterioration of beta cell mass through induction of apoptosis. Mitochondrial stress plays a critical role in mediating apoptosis by releasing cytochrome C into the cytoplasm, directly activating caspase-9 and its downstream signalling cascade. We aimed to identify new compounds that protect beta cells from cytokine-induced activation of the intrinsic (mitochondrial) pathway of apoptosis. Experimental Approach: Diabetogenic media, composed of IL-1β, IFN-γ and high glucose, were used to induce mitochondrial stress in rat insulin-producing INS1E cells, and a high-content image-based screen of small molecule modulators of Casp9 pathway was performed. Key Results: A novel small molecule, ATV399, was identified from a high-content image-based screen for compounds that inhibit cleaved caspase-9 activation and subsequent beta cell apoptosis induced by a combination of IL-1β, IFN-γ and high glucose, which together mimic the pathogenic diabetic milieu. Through medicinal chemistry optimization, potency was markedly improved (6–30 fold), with reduced inhibitory effects on CYP3A4. Improved analogues, such as CAT639, improved beta cell viability and insulin secretion in cytokine-treated rat insulin-producing INS1E cells and primary dispersed islet cells. Mechanistically, CAT639 reduced the production of NO by allosterically inhibiting dimerization of inducible NOS (iNOS) without affecting its mRNA levels. Conclusion and Implications: Taken together, these studies demonstrate a successful phenotypic screening campaign resulting in identification of an inhibitor of iNOS dimerization that protects beta cell viability and function through modulation of mitochondrial stress induced by cytokines.

Fluorine-free blue-green emitters for light-emitting electrochemical cells

There is presently a lack of efficient and stable blue emitters for light-emitting electrochemical cells (LEECs), which limits the development of white light emitting systems for lighting. Cyclometalated iridium complexes as blue emitters tend to show low photoluminescence efficiency due to significant ligand-centred character of the radiative transition. The most common strategy to blue-shift the emission is to use fluorine substituents on the cyclometalating ligand, such as 2,4-difluorophenylpyridine, dFppy, which has been shown to decrease the stability of the emitter in operating devices. Herein we report a series of four new charged cyclometalated iridium complexes using methoxy- and methyl-substituted 2,3′-bipyridine as the main ligands. The combination of donor groups and the use of a cyclometalated pyridine has been recently reported for neutral complexes and found electronically equivalent to dFppy. We describe the photophysical and electrochemical properties of the complexes in solution and use DFT and TDDFT calculations to gain insights into their properties. The complexes exhibit bluish-green emission with onsets around 450 nm, which correspond to the maximum emission at 77 K. Furthermore, photoluminescence quantum yields in solution are all above 40%, with the brightest in the series at 66%. Finally, LEECs were prepared using these complexes as the emissive material to evaluate the performance of this particular design. Compared to previously reported devices with fluorine-containing emitters, the emitted colours are slightly red-shifted due to methyl substituents on the coordinating pyridine of the main ligand and overall device performances, unfortunately including the stability of devices, are similar to those previously reported. Interestingly within the series of complexes there appears to be a positive effect of the methoxy-substituents on the stability of the devices. The poor stability is therefore attributed to the combination of cyclometalated pyridine and methoxy groups. the Partner Organisations 2014.

BI-ARYL AMINOTETRALINES

The invention is concerned with the compounds of formula I: and pharmaceutically acceptable salts and esters thereof, wherein R1-R5, A, B, Q, W, and X are defined in the detailed description and claims. In addition, the present invention relates to methods of manufacturing and using the compounds of formula I as well as pharmaceutical compositions containing such compounds. The compounds of formula I are antagonists at the CRTH2 receptor and may be useful in treating diseases and disorders associated with that receptor such as asthma.

Design, synthesis, and biological evaluation of 8-biarylquinolines: A novel class of PDE4 inhibitors

The structure-activity relationship of a novel series of 8-biarylquinolines acting as type 4 phosphodiesterase (PDE4) inhibitors is described herein. Prototypical compounds from this series are potent and non-selective inhibitors of the four distinct PDE4 (IC50 50 0.5 μM) the LPS-induced release of the cytokine TNF-α. Optimized inhibitors were evaluated in vivo for efficacy in an ovalbumin-induced bronchoconstriction model in conscious guinea pigs. Their propensity to produce an emetic response was evaluated by performing pharmacokinetic studies in squirrel monkeys. This work has led to the identification of several compounds with excellent in vitro and in vivo profiles, including a good therapeutic window of efficacy over emesis.

AMIDE COMPOUNDS AS ION CHANNEL LIGANDS AND USES THEREOF

Compounds are disclosed that have a formula represented by the following: The compounds may be prepared as pharmaceutical compositions, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, pain, inflammation, traumatic injury, and others.