163105-89-3

Basic information

• Product Name: 2-Methoxy-5-pyridineboronic acid
• Synonyms: 6-Methoxy-3-pyridinylboronic acid,2-Methoxy-5-pyridineboronic acid;2-Methoxy-5-pyridine;2-Methoxy-5-pyridine acid;2-Methoxypyridine-5-boronic Acid (contains varying aMounts of Anhydride);6-Methoxy-3-pyridineboronic acid;2-Methorypyridine-5-boronic acid;6-Methoxy-3-pyridylboronic Acid;2-Methoxy-5-pyridineboronic acid (contains varying aMounts of anhydride)
• CAS NO: 163105-89-3
• Molecular Formula: C6H8BNO3
• Molecular Weight: 152.94
• EINECS: 1312995-182-4
• Product Categories: Boronate Ester;Potassium Trifluoroborate;blocks;BoronicAcids;Pyridines;Pyridine;Boronic Acids & Esters;Boronic acids;Heterocyclic Compounds;Alkoxy;Organoborons;Boronic Acids & Esters;Boronic Acid;Boronic Acids;Boronic Acids and Derivatives;Heteroaryl;Boric acid series
• Mol File: 163105-89-3.mol

Chemical Properties

• Melting Point: 135-140 °C(lit.)
• Boiling Point: 313.2 °C at 760 mmHg
• Flash Point: 143.2 °C
• Appearance: White to beige powder
• Density: 1.249 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.524
• Storage Temp.: 0-6°C
• PKA: 7.26±0.10(Predicted)
• Water Solubility: Soluble in water.
• BRN: 9119950
• CAS DataBase Reference: 2-Methoxy-5-pyridineboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methoxy-5-pyridineboronic acid(163105-89-3)
• EPA Substance Registry System: 2-Methoxy-5-pyridineboronic acid(163105-89-3)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-22
• Safety Statements: 22-24/25-36/37/39-26-23
• WGK Germany: 3
• HazardClass: IRRITANT, AIR SENSITIVE, KEEP CO
• Hazardous Substances Data: 163105-89-3(Hazardous Substances Data)

Usage

Uses

Used in Cosmetics Industry:
2-Methoxy-5-pyridineboronic acid is used as a functional ingredient in the cosmetics industry for its potential skin care benefits. It may contribute to the development of formulations that can improve skin health and appearance.
Used in Coatings Industry:
In the coatings industry, 2-Methoxy-5-pyridineboronic acid is utilized as a component in the formulation of various types of coatings. Its chemical properties may enhance the performance characteristics of the coatings, such as durability, adhesion, and resistance to environmental factors.
Used in Candle Making:
2-Methoxy-5-pyridineboronic acid is also employed in the candle making process. It can be used to improve the quality and performance of candles, potentially offering benefits such as better burn time, reduced smoke, and enhanced fragrance release.

InChI:InChI=1/C6H8BNO3/c1-11-6-3-2-5(4-8-6)7(9)10/h2-4,9-10H,1H3

Upstream product

• 13472-85-0 2-methoxy-5-bromopyridine 
• 121-43-7 Trimethyl borate 
• 5419-55-6 Triisopropyl borate 
• 624-28-2 2,5-dibromopyridine 
• 1628-89-3 2-methoxypyridine 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 381725-49-1 2-methoxy-5-(pyridin-2-yl)pyridine 
• 95881-82-6 6,6′-dimethoxy-3,3′-bipyridine 
• 835876-08-9 6'-methoxy[2,3']bipyridin-5-ylamine 
• 835876-03-4 4-(6-methoxypyridin-3-yl)phenylamine 
• 879498-82-5 methyl 3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-2-(6-methoxypyridin-3-yl)-1H-indole-6-carboxylate 
• 876625-74-0 (3S)-1-[(2S,3S)-2-[(tert-butoxycarbonyl)amino]-3-[4-(6-methoxypyridin-3-yl)phenyl]-1-oxobutanyl]-3-fluoropyrrolidine 
• 15871-85-9 6-methoxynicotinonitrile 
• 53698-47-8 2-methoxy-5-phenylpyridine 
• 954138-07-9 3-(4-(2-hydroxyethyl)piperazin-1-yl)-7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2(1H)-one 
• 1013101-36-4 2-amino-8-(cis-4-(2-hydroxyethoxy)cyclohexyl)-6-(6-methoxypyridin-3-yl)-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one 
• 945375-78-0 5-(6-methoxypyridin-3-yl)pyridin-2-amine 

Relevant articles and documents

Functionalized pyridylboronic acids and their Suzuki cross-coupling reactions to yield novel heteroarylpyridines

2-Bromo-5-pyridylboronic acid 2a, 2-chloro-5-pyridylboronic acid 2b, 2-methoxy-5-pyridylboronic acid 2c, and 5-chloro-2-methoxy-4-pyridylboronic acid 4 have been synthesized and shown to undergo palladium-catalyzed cross-coupling reactions with heteroaryl bromides to yield novel heteroarylpyridine derivatives. The X-ray crystal structures of 2a and 2b have been obtained.

PYRAZOLOPYRIMIDINE DERIVATIVE AND USE THEREOF AS PI3K INHIBITOR

The present invention discloses a series of pyrazolopyrimidine derivatives and use thereof in preparing a medicament for treating a disease related to PI3K, and in particular, discloses a derivative compound of formula (I), a tautomer thereof or a pharmaceutically acceptable composition thereof.

COMBINATION THERAPY WITH A PHOSPHOINOSITIDE 3-KINASE INHIBITOR WITH A ZINC BINDING MOIETY

The invention provides a method of treating cancer in a subject in need thereof, comprising administering to the subject: (a) a compound of Formula I: or a pharmaceutically acceptable salt thereof, wherein R is hydrogen or an acyl group; and (b) a PD-1 signaling inhibitor; wherein the compound of Formula I or pharmaceutically acceptable salt thereof and the PD-1 signaling inhibitor are administered in amounts which in combination are therapeutically effective. The invention further provides a pharmaceutical composition comprising a compound of Formula I or a pharmaceutically acceptable salt thereof, a PD-1 signaling inhibitor and a pharmaceutically acceptable carrier or excipient.

Copper-Catalyzed Monoorganylation of Trialkyl Borates with Functionalized Organozinc Pivalates

Organozinc pivalates, a recently developed air- and moisture-stable organozinc species, were found for the first time as excellent organometallic species in the monoorganylation of trialkyl borates whereby boronic acids were prepared in high yields. The significant advantage of organozinc pivalates over another previously employed organometallic reagents, e. g., organolithium reagents, Grignard reagents and organozinc halides, is that the generation of multiorganylation byproducts such as borinic acids and trialkylboranes were completely suppressed. Additionally, the in situ generated boronates could be directly arranged into Suzuki-Miyaura type cross-coupling reactions to produce biaryls in high yields.

COMBINATION THERAPY WITH A PHOSPHOINOSITIDE 3-KINASE INHIBITOR WITH A ZINC BINDING MOIETY

The invention provides a method of treating cancer in a subject in need thereof, comprising administering to the subject: (a) a compound of Formula I: or a pharmaceutically acceptable salt thereof, wherein R is hydrogen or an acyl group; and (b) a BCL-2 inhibitor; wherein the compound of Formula I or pharmaceutically acceptable salt thereof and a BCL-2 inhibitor are administered in amounts which in combination are therapeutically effective. The invention further provides a pharmaceutical composition comprising a compound of Formula I or a pharmaceutically acceptable salt thereof, a BCL-2 inhibitor and a pharmaceutically acceptable carrier or excipient.

Phosphoinositide 3-kinase inhibitor with a zinc binding moiety

The invention provides a compound of Formula I, Pharmaceutical compositions comprising such compounds and the use of such compounds in the treatment of phosphoinositide 3-kinase related diseases and disorders such as cancer. The instant application further relates to the treatment of histone deacetylase related disorders and diseases related to both histone deacetylase and phosphoinositide 3-kinase.

Discovery of 2-(2-Oxo-1-phenyl-5-pyridin-2-yl-1,2-dihydropyridin-3-yl) benzonitrile (Perampanel): A novel, noncompetitive α-amino-3-hydroxy-5- methyl-4-isoxazolepropanoic acid (AMPA) receptor antagonist

Dysfunction of glutamatergic neurotransmission has been implicated in the pathogenesis of epilepsy and numerous other neurological diseases. Here we describe the discovery of a series of 1,3,5-triaryl-1H-pyridin-2-one derivatives as noncompetitive antagonists of AMPA-type ionotropic glutamate receptors. The structure-activity relationships for this series of compounds were investigated by manipulating individual aromatic rings located at positions 1, 3, and 5 of the pyridone ring. This culminated in the discovery of 2-(2-oxo-1-phenyl-5- pyridin-2-yl-1,2-dihydropyridin-3-yl)benzonitrile (perampanel, 6), a novel, noncompetitive AMPA receptor antagonist that showed potent activity in an in vitro AMPA-induced Ca2+ influx assay (IC50 = 60 nM) and in an in vivo AMPA-induced seizure model (minimum effective dose of 2 mg/kg po). Perampanel is currently in regulatory submission for partial-onset seizures associated with epilepsy.

Novel bisaryl substituted thiazoles and oxazoles as highly potent and selective peroxisome proliferator-activated receptor δ agonists

The discovery, synthesis, and optimization of compound 1 from a high-throughput screening hit to highly potent and selective peroxisome proliferator-activated receptor δ (PPARδ) agonists are reported. The synthesis and structure-activity relationship in this series are described in detail. On the basis of a general schematic PPAR pharmacophore model, scaffold 1 was divided into headgroup, linker, and tailgroup and successively optimized for PPAR activation using in vitro PPAR transactivation assays. A (2-methylphenoxy)acetic acid headgroup, a flexible linker, and a five-membered heteroaromatic center ring with two hydrophobic aryl substituents were required for efficient and selective PPARδ activation. The fine-tuning of these aryl substituents led to an array of highly potent and selective compounds such as compound 38c, displaying an excellent pharmacokinetic profile in mouse. In an in vivo acute dosing model, selected members of this array were shown to induce the expression of pyruvate dehydrogenase kinase-4 (PDK4) and uncoupling protein-3 (UCP3), genes that are known to be involved in energy homeostasis and regulated by PPARδ in skeletal muscle.

1H-INDOLE-2-CARBOXYLIC ACID DERIVATIVES USEFUL AS PPAR MODULATORS

The present invention relates to certain indole derivatives that are modulators of PPAR, to processes for their preparation, to pharmaceutical compositions containing them and to their use in medicine.

Pyrazolopyridine-4-Yl Pyridazinone Derivatives and Addition Salts Thereof, and Pde Inhibitors Comprising the Same Derivatives or Salts as Active Ingredient

Novel pyrazolopyridine-4-yl pyridazinone derivatives serve as phosphodiesterase inhibitors and are useful compounds for use in pharmaceutical products. Specifically, the compounds of the present invention are pyrazolopyridine-4-yl pyridazinone derivatives represented by the following general formula (1): (Example: 6-(2-ethyl-7-methoxy-pyrazolo[1,5-a]pyridine-4-yl)-5-methyl-4, 5-dihydro-3(2H)-pyridazinone).