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 
• 98279-57-3 (4-oxo-4H-[1]pyridyloxy)-acetic acid 
• 60-29-7 diethyl ether 
• 67-56-1 methanol 
• 5421-92-1 1-(4-pyridyl)pyridinium chloride hydrochloride 
• 39910-67-3 4-azidopyridine 
• 1124-33-0 4-nitraminopyridine N-oxide 
• 626-61-9 4-Chloropyridine 
• 124-41-4 sodium methylate 
• 56898-50-1 4-methoxypyridine borane complex 
• 1120-87-2 4-bromopyridin 
• 38050-71-4 9-methoxy-9-BBN 
• 7647-14-5 sodium chloride 
• 1122-58-3 dmap 

Downstream Products

• 126378-84-5 (RS)-2-phenyl-2,3-dihydro-1H-pyridin-4-one 
• 282534-52-5 4-oxo-2-propenyl-3,4-dihydro-2H-pyridine-1-carboxylic acid benzyl ester 
• 335265-99-1 2-ethenyl-3,4-dihydro-4-oxo-1(2H)-pyridinecarboxylic acid phenylmethyl ester 
• 369390-19-2 2-(allyldimethylsilanylmethyl)-4-oxo-3,4-dihydro-2H-pyridine-1-carboxylic acid benzyl ester 
• 630115-82-1 2-(2-methylprop-2-enyl)-3,4-dihydro-4-oxo-1(2H)-pyridinecarboxylic acid phenylmethyl ester 
• 630115-81-0 2-allyl-3,4-dihydro-4-oxo-1(2H)-pyridinecarboxylic acid phenylmethyl ester 
• 128351-72-4 4-Methoxy-2-methyl-2H-pyridine-1-carboxylic acid phenyl ester 
• 325486-45-1 tert-butyl 4-oxo-3,4-dihydropyridine-1(2H)-carboxylate 
• 57330-84-4 ethyl 3,4-dihydro-4-oxo-1(2H)-pyridinecarboxylate 
• 185847-84-1 benzyl 4-oxo-3,4-dihydropyridine-1(2H)-carboxylate 

Relevant articles and documents

Photocatalytic deoxygenation of N-O bonds with rhenium complexes: From the reduction of nitrous oxide to pyridineN-oxides

The accumulation of nitrogen oxides in the environment calls for new pathways to interconvert the various oxidation states of nitrogen, and especially their reduction. However, the large spectrum of reduction potentials covered by nitrogen oxides makes it difficult to find general systems capable of efficiently reducing variousN-oxides. Here, photocatalysis unlocks high energy species able both to circumvent the inherent low reactivity of the greenhouse gas and oxidant N2O (E0(N2O/N2) = +1.77 Vvs.SHE), and to reduce pyridineN-oxides (E1/2(pyridineN-oxide/pyridine) = ?1.04 Vvs.SHE). The rhenium complex [Re(4,4′-tBu-bpy)(CO)3Cl] proved to be efficient in performing both reactions under ambient conditions, enabling the deoxygenation of N2O as well as synthetically relevant and functionalized pyridineN-oxides.

Copper-Catalyzed Methoxylation of Aryl Bromides with 9-BBN-OMe

A Cu-catalyzed cross-coupling reaction between aryl bromides and 9-BBN-OMe to provide aryl methyl ethers under mild conditions is reported. The oxalamide ligand BHMPO plays a key role in the transformation. Various functional groups on bromobenzenes are well tolerated, providing the desired anisole products in moderate to high yields.

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.