4-methoxyphenyl

Base Information

• Chemical Name: 4-methoxyphenyl
• CAS No.: 2396-03-4
• Molecular Formula: C7H7O
• Molecular Weight: 107.132
• Mol file: 2396-03-4.mol

Synonyms:

Chemical Property of 4-methoxyphenyl

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: Other names for **4-methoxyphenyl** include **p-methoxyphenyl** and **4-anisyl**. The study demonstrates that **4-methoxyphenyl radicals (4-MeO-Ph·)** are generated via a one-electron transfer process from the reaction of **4-methoxybenzenediazonium tetrafluoroborate** with melanin and catechol derivatives. This radical formation is autocatalytic, driven by the production of *o*-quinones, and proceeds efficiently in the presence of oxygen, leading to oxygen consumption. Tyrosinase-activated phenols, particularly tyrosine, enhance this reduction, highlighting the necessity of *o*-dihydroxybenzene structures for aryl radical generation. The findings suggest that hydroquinones and semiquinone radicals facilitate diazonium salt homolysis, which may have implications for the biological and toxicological effects of such compounds.

Technology Process of 4-methoxyphenyl

There total 6 articles about 4-methoxyphenyl which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

p-methoxybenzenediazonium (17333-79-8) + α-hydroxybenzyl radical (2406-15-7) → 4-methoxyphenyl radical (2396-03-4) + benzaldehyde (100-52-7)

Guidance literature:

In water; Rate constant;

Reference yield:

C13H12IO → iodobenzene (591-50-4) + phenyl radical (2396-01-2) + para-iodoanisole (696-62-8) + 4-methoxyphenyl radical (2396-03-4)

Guidance literature:

With chromium dichloride; In N,N-dimethyl-formamide; at 25 ℃; Kinetics;

DOI:10.1021/jo990809y

Reference yield:

9-(3-Methoxy-phenyl)-9-phenyl-dodecahydro-fluorene (78229-10-4) → phenyl radical (2396-01-2) + 4-methoxyphenyl radical (2396-03-4) + C19H25Li + C20H27LiO

Guidance literature:

With lithium; In 1,2-dimethoxyethane; at 35 ℃; Rate constant; var. metals;

DOI:10.1021/ja00239a034

upstream raw materials:

p-methoxybenzenediazonium

α-hydroxybenzyl radical

para-methoxyphenyldiazonium chloride

4-methoxybenzenediazonium tetrafluoroborate

Downstream raw materials:

1-bromo-4-methoxy-benzene

(4-D)-Anisol

methoxybenzene

Refernces

A formal total synthesis of eleutherobin using the ring-closing metathesis (RCM) reaction of a densely functionalized diene as the key step: Investigation of the unusual kinetically controlled RCM stereochemistry

10.1002/chem.200500749

The research presents a formal total synthesis of eleutherobin, a natural product with antitumor activity. The key step of the strategy involves a ring-closing metathesis (RCM) reaction of a densely functionalized diene. The study investigates the unusual kinetically controlled RCM stereochemistry using computational methods. The synthesis begins with the preparation of aldehyde 6 from R-(–)-carvone through a series of reactions, which is then converted into diene 5 via stereoselective titanium-mediated Hafner–Duthaler oxyallylation reactions. The RCM reaction of diene 5 using Grubbs' second-generation catalyst leads to the formation of the ten-membered carbocycle (E)-14, which is less thermodynamically stable but formed under kinetic control. Further transformations including removal of protective groups and oxidation lead to the key intermediate 3, which is identical to the data reported by Danishefsky and co-workers. The research also explores the stereochemical outcome of the RCM reaction and the subsequent isomerization of the enedione using molecular mechanics, semiempirical PM3 calculations, and density functional theory (DFT) calculations. The study highlights the role of the p-methoxyphenyl (PMP) protective group in facilitating the RCM reaction and the formation of the kinetically controlled E isomer.

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