54536-21-9

Basic information

• Product Name: 1-methoxy-4-((D₃)-methoxy)benzene
• Synonyms: 1-methoxy-4-((D₃)-methoxy)benzene
• CAS NO: 54536-21-9
• Molecular Weight: 141.142
• Mol File: 54536-21-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1-methoxy-4-((D₃)-methoxy)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methoxy-4-((D₃)-methoxy)benzene(54536-21-9)
• EPA Substance Registry System: 1-methoxy-4-((D₃)-methoxy)benzene(54536-21-9)

Safety Data

• Hazardous Substances Data: 54536-21-9(Hazardous Substances Data)

Upstream product

• 1849-29-2 1,1,1-trideuteromethanol 
• 696-62-8 para-iodoanisole 
• 23726-00-3 <²H9>trimethylsulphoxonium iodide 
• 150-76-5 4-methoxy-phenol 
• 865-50-9 iodomethane-d3 
• 106-39-8 bromochlorobenzene 
• 623-12-1 4-chloromethoxybenzene 

Downstream Products

• 54536-24-2 p-methoxyphenol-d3 
• 150-76-5 4-methoxy-phenol 

Relevant articles and documents

Oxalic Diamides and tert-Butoxide: Two Types of Ligands Enabling Practical Access to Alkyl Aryl Ethers via Cu-Catalyzed Coupling Reaction

A robust and practical protocol for preparing alkyl aryl ethers has been developed, which relies on using two types of ligands to promote Cu-catalyzed alkoxylation of (hetero)aryl halides. The reaction scope is very general for a variety of coupling partners, particularly for challenging secondary alcohols and (hetero)aryl chlorides. In case of coupling with aryl chlorides and bromides, two oxalic diamides serve as the powerful ligands. The tert-butoxide is first demonstrated as a ligand for Cu-catalyzed coupling reaction, leading to alkoxylation of aryl iodides complete at room temperature. Additionally, a number of carbohydrate derivatives are applicable for this coupling reaction, affording the corresponding carbohydrate-aryl ethers in 29-98% yields.

Stereochemistry of the Menthyl Grignard Reagent: Generation, Composition, Dynamics, and Reactions with Electrophiles

Menthyl Grignard reagent 1 from either menthyl chloride (2) or neomenthyl chloride (3) consists of menthylmagnesium chloride (1a), neomenthylmagnesium chloride (1b), trans-p-menthane (4), 2-menthene (8), 3-menthene (9), and Wurtz coupling products including symmetrical bimenthyl 13. The diastereomeric ratio 1a/1b was determined in situ by 13C NMR or after D2O quenching by 2H NMR analysis. Hydrolysis of the C-Mg bond proceeds with retention of configuration at C-1. The kinetic ratio 1a/1b from Grignard reagent generation (dr 59:41 at 50 °C in THF) is close to the thermodynamic ratio (56:44 at 50 °C in THF). Carboxylation of 1 at -78 °C separates diastereomers 1a/b to give the anion of menthanecarboxylic acid (19) from 1a, which combines with unreactive 1b to give neomenthylmagnesium menthanecarboxylate (1bI). The kinetics of epimerization for the menthyl/neomenthylmagnesium system was analyzed (ΔH? = 98.5 kJ/mol, ΔS? = -113 J/mol·K for 1bI → 1aI). Reactions of 1 with phosphorus electrophiles proceed stereoconvergently at C-1 of 1a/b to give predominantly menthyl-configured substitution products: PCl3 and 2 equiv of 1 give Men2PCl (6), which hydrolyzes to dimenthylphosphine P-oxide (7), whereas Ph2PCl with 1 equiv of 1 gave P-menthyldiphenylphosphine oxide (27) after workup in air.