620-08-6

Basic information

• Product Name: 4-Methoxypyridine
• Synonyms: gamma-Methoxypyridine;4-METHOXYPYRIDINE;METHYL PYRIDIN-4-YL ETHER;4-methoxypridine;Pyridine, 4-methoxy-;4-METHOXYPYRIDINE, 98+%;4-Methoxypyridine,99%;4-methoxyridine
• CAS NO: 620-08-6
• Molecular Formula: C₆H₇NO
• Molecular Weight: 109.13
• EINECS: 210-624-7
• Product Categories: blocks;Pyridines;Pyridine;Pyridines, Pyrimidines, Purines and Pteredines;Pyridine series;Pyridine Derivertives;Boronic Acid;C6;Heterocyclic Building Blocks
• Mol File: 620-08-6.mol
• Article Data: 55

Chemical Properties

• Melting Point: 4 °C
• Boiling Point: 191 °C
• Flash Point: 74 °C
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 1.075 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.18mmHg at 25°C
• Refractive Index: 1.518-1.522
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 6.58(at 25℃)
• BRN: 108211
• CAS DataBase Reference: 4-Methoxypyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methoxypyridine(620-08-6)
• EPA Substance Registry System: 4-Methoxypyridine(620-08-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-20/21/22
• Safety Statements: 37/39-26-36-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 620-08-6(Hazardous Substances Data)

Usage

Description

4-Methoxypyridine is an organic compound with the chemical formula C6H7NO and is derived from pyridine by the addition of a methoxy group at the 4th position. It is a clear colorless to slightly yellow liquid and has been prepared from 4-methoxypyridine-N-oxide through catalytic hydrogenation. Ortho lithiation of 4-methoxypyridine using mesityllithium as the metalating base has been studied.

Uses

Used in Pharmaceutical Industry:
4-Methoxypyridine is used as a building block for the synthesis of some biologically active compounds, making it a valuable component in the development of new medications. Its role in the creation of various pharmaceuticals highlights its importance in this industry.
Used in Protein Farnesyltransferase Inhibitors:
4-Methoxypyridine is utilized for the preparation of a new series of benzoylated N-ylides, which act as protein farnesyltransferase inhibitors. These inhibitors play a crucial role in the regulation of cellular processes, such as signal transduction and protein prenylation, and have potential applications in the treatment of various diseases, including cancer.
Used in Stereocontrolled Synthesis:
4-Methoxypyridine serves as a starting reagent for the stereocontrolled synthesis of (±)-pumiliotoxin C and (±)-lasubine II. These complex organic compounds have potential applications in the development of new drugs and therapeutic agents.
Used in Neuronal Nicotinic Acetylcholine Receptor Ligands:
4-Methoxypyridine is also used in the efficient construction of dihyropyridin-4-ones, which serve as potential ligands for neuronal nicotinic acetylcholine receptors. These ligands are essential for understanding the function of these receptors and may contribute to the development of treatments for neurological disorders.

InChI:InChI=1/C6H7NO/c1-8-6-2-4-7-5-3-6/h2-5H,1H3

Upstream product

• 186581-53-3 diazomethane 
• 626-64-2 pyridin-4-ol 
• 60-29-7 diethyl ether 
• 626-61-9 4-Chloropyridine 
• 124-41-4 sodium methylate 
• 67-56-1 methanol 
• 5421-92-1 1-(4-pyridyl)pyridinium chloride hydrochloride 
• 1122-96-9 4-methoxypyridine N-oxide 
• 39910-67-3 4-azidopyridine 
• 93560-55-5 2-iodo-3-methoxy-pyridine 
• 82257-09-8 bromo-3 methoxy-4 pyridine 
• 1124-33-0 4-nitraminopyridine N-oxide 
• 142929-26-8 4-Methoxy-3-(trimethylstannyl)pyridin 
• 96245-98-6 2,3-dibromo-4-methoxypyridine 

Downstream Products

• 872-50-4 1-methyl-pyrrolidin-2-one 
• 126378-42-5 4-methoxy-3-(trisopropylsilyl)pyridine 
• 87-85-4 hexamethylbenzene radical cation 
• 118006-05-6 4-Methoxy-3-phenylselanyl-pyridine 
• 5005-38-9 α-phenyl-4-pyridylacetonitrile 
• 96530-17-5 N-(4-methoxyphenyl)monoaza-12-crown-4 
• 119-65-3 isoquinoline 
• 74414-99-6 N-(methoxycarbonyl)-4-methoxypyridinium ion 
• 118006-04-5 1-(4-metoxy-3-pyridyl) phenylmethanol 
• 142003-71-2 (4-Methoxy-2-propyl-2H-pyridin-1-yl)-phenyl-methanone 
• 168105-12-2 (2R,2'R,4S)-methyl 2-(tert-butyl)-3'-<(1',2',3',4'-tetrahydro-4-oxo-2'-phenylpyridin-1'-yl)carbonyl>-1,3-oxazolidine-4-carboxylate 
• 131426-68-1 (-)-1-((1R,2S,5R)-8-phenylmenthoxycarbonyl)-(S)-2-triphenylsilyl-2,3-dihydro-4-pyridone 
• 107971-44-8 N-<(benzyloxy)carbonyl>-2-(4-hydroxybutyl)-2,3-dihydro-4-pyridone 
• 116725-72-5 N-<(benzyloxy)carbonyl>-2-(3,4-dimethoxyphenyl)-4-oxo-1,2,3,4-tetrahydropyridine 

Relevant articles and documents

Lewis Acidic Boranes, Lewis Bases, and Equilibrium Constants: A Reliable Scaffold for a Quantitative Lewis Acidity/Basicity Scale

A quantitative Lewis acidity/basicity scale toward boron-centered Lewis acids has been developed based on a set of 90 experimental equilibrium constants for the reactions of triarylboranes with various O-, N-, S-, and P-centered Lewis bases in dichloromethane at 20 °C. Analysis with the linear free energy relationship log KB=LAB+LBB allows equilibrium constants, KB, to be calculated for any type of borane/Lewis base combination through the sum of two descriptors, one for Lewis acidity (LAB) and one for Lewis basicity (LBB). The resulting Lewis acidity/basicity scale is independent of fixed reference acids/bases and valid for various types of trivalent boron-centered Lewis acids. It is demonstrated that the newly developed Lewis acidity/basicity scale is easily extendable through linear relationships with quantum-chemically calculated or common physical–organic descriptors and known thermodynamic data (ΔH (Formula presented.)). Furthermore, this experimental platform can be utilized for the rational development of borane-catalyzed reactions.

A Lewis Base Nucleofugality Parameter, NFB, and Its Application in an Analysis of MIDA-Boronate Hydrolysis Kinetics

The kinetics of quinuclidine displacement of BH3 from a wide range of Lewis base borane adducts have been measured. Parameterization of these rates has enabled the development of a nucleofugality scale (NFB), shown to quantify and predict the leaving group ability of a range of other Lewis bases. Additivity observed across a number of series R′3-nRnX (X = P, N; R′ = aryl, alkyl) has allowed the formulation of related substituent parameters (nfPB, nfAB), providing a means of calculating NFB values for a range of Lewis bases that extends far beyond those experimentally derived. The utility of the nucleofugality parameter is explored by the correlation of the substituent parameter nfPB with the hydrolyses rates of a series of alkyl and aryl MIDA boronates under neutral conditions. This has allowed the identification of MIDA boronates with heteroatoms proximal to the reacting center, showing unusual kinetic lability or stability to hydrolysis.

Selective and Efficient Photoinactivation of Intracellular Staphylococcus aureus and MRSA with Little Accumulation of Drug Resistance: Application of a Ru(II) Complex with Photolabile Ligands

Novel antibacterial agents capable of efficiently sterilizing intracellular Staphylococcus aureus and methicillin-resistant S. aureus (MRSA) but with low cytotoxicity and low resistance development are quite appealing. In this work, three Ru(II) complexes with photolabile ligands were explored to realize such a goal. Complex 3 (5 μM) can inhibit more than 90% growth of S. aureus/MRSA that has invaded in J774A.1 cells upon visible light irradiation, being much more efficient than vancomycin. In similar conditions, negligible dark- and phototoxicity were found toward the host cells. The bactericidal activity is highly correlated with DNA covalent binding by the Ru(II) fractions generated after ligand photodissociation. Moreover, S. aureus quickly developed resistance toward vancomycin, while negligible resistance toward complex 3 even after 700 generations was obtained. These appealing results may pave a new way for fighting against intracellular antibiotic-resistant pathogens.