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

Chemical Properties

clear colorless to slightly yellow liquid

Uses

Different sources of media describe the Uses of 620-08-6 differently. You can refer to the following data:
1. 4-Methoxypyridine, is used as a building block for the synthesis of some biologically active compounds. It is used for the preparation of a new series of benzoylated N-ylides as protein farnesyltransferase inhibitors.
2. 4-Methoxypyridine was used as a starting reagent for the stereocontrolled synthesis of (±)-pumiliotoxin C and (±)-lasubine II. It was also used in an efficient construction of dihyropyridin-4-ones, which serves as potential ligands for neuronal nicotinic acetycholine receptors.

General Description

4-Methoxypyridine has been prepared from 4-methoxypyridine-N-oxide, via catalytic hydrogenation. Ortho lithiation of 4-methoxypyridine using mesityllithium as the metalating base has been studied.

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

Upstream product

• 67-56-1 methanol 
• 5421-92-1 1-(4-pyridyl)pyridinium chloride hydrochloride 
• 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 
• 855-38-9 P(p-CH₃OC₆H₄)3 
• 7732-18-5 water 
• 1122-58-3 dmap 
• 1120-87-2 4-bromopyridin 
• 38050-71-4 9-methoxy-9-BBN 
• 626-61-9 4-Chloropyridine 
• 124-41-4 sodium methylate 
• 56898-50-1 4-methoxypyridine borane complex 

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

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.

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.