22865-60-7

Basic information

• Product Name: Benzene, 1-methoxy-4-[(4-methylphenyl)methyl]-
• CAS NO: 22865-60-7
• Molecular Formula: C15H16O
• Molecular Weight: 212.291
• Mol File: 22865-60-7.mol
• Article Data: 54

Chemical Properties

• CAS DataBase Reference: Benzene, 1-methoxy-4-[(4-methylphenyl)methyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-methoxy-4-[(4-methylphenyl)methyl]-(22865-60-7)
• EPA Substance Registry System: Benzene, 1-methoxy-4-[(4-methylphenyl)methyl]-(22865-60-7)

Safety Data

• Hazardous Substances Data: 22865-60-7(Hazardous Substances Data)

Upstream product

• 589-18-4 4-Methylbenzyl alcohol 
• 100-66-3 methoxybenzene 
• 998-41-4 tributylsilane 
• 429677-37-2 (p-methoxyphenyl)(p-tolyl)methylium cation 
• 838-22-2 4-methoxy-4'-methylbenzhydrol 
• 766-77-8 Dimethylphenylsilane 
• 3395-83-3 4-methylbenzaldehyde dimethylacetal 
• 104-82-5 4-Methylbenzyl chloride 
• 789-25-3 HSiPh₃ 
• 5689-71-4 2-(4-methoxy-phenyl)-[1,3]dioxane 
• 108-88-3 toluene 
• 123-11-5 4-methoxy-benzaldehyde 
• 39619-60-8 trans,trans-2,5-Heptadien 
• 1165952-92-0 cyclohexa-1,4-diene 

Downstream Products

• 28994-46-9 4-(4-methylbenzyl)phenol 
• 134310-99-9 4-(4-methoxyphenyl)-4-(4-methylphenyl)-1-butene 
• 429677-37-2 (p-methoxyphenyl)(p-tolyl)methylium cation 
• 33667-91-3 N-(4-methoxyphenyl)-4-methylbenzamide 
• 39192-94-4 N-(p-methylphenyl)-p-methoxybenzamide 
• 116664-87-0 (4-methylphenyl)-(4'-methoxyphenyl)methyl acetate 

Relevant articles and documents

A novel and efficient route to diarylmethanes catalyzed by nickel(II) ion on nanoporous carbon

Much improved catalytic carbon-carbon bond-forming reactions between aryl chlorides and Grignard reagents has been achieved using nickel(II) ion on nanoporous carbon.

Mixed Alkyl/Aryl Diphos Ligands for Iron-Catalyzed Negishi and Kumada Cross Coupling Towards the Synthesis of Diarylmethane

Mixed alkyl/aryl diphos ligands have been prepared and their application in iron-catalyzed cross coupling of benzylic chlorides with diaryl zinc (Negishi) or aryl Grignard reagents (Kumada) towards the synthesis of diarylmethane has been evaluated. The iron?diphos catalytic system exhibited the enhanced activity and selectivity in the two coupling reactions. The electron-rich mixed PPh2/PCy2 ligands outperformed their symmetrical PPh2 congeners, and led to decreased homocoupling byproduct formation. It indicates that the electronic effect of the ligands plays an important role in the catalytic performance. The Fe catalyst supported by L8 bearing an electron-rich PCy2 substituent and a sterically demanding tert-butyl on ethene backbone exhibited the best catalytic performance and good functional group tolerance in the two cross coupling reactions.

Dynamic Kinetic Cross-Electrophile Arylation of Benzyl Alcohols by Nickel Catalysis

Catalytic transformation of alcohols via metal-catalyzed cross-coupling reactions is very important, but it typically relies on a multistep procedure. We here report a dynamic kinetic cross-coupling approach for the direct functionalization of alcohols. The feasibility of this strategy is demonstrated by a nickel-catalyzed cross-electrophile arylation reaction of benzyl alcohols with (hetero)aryl electrophiles. The reaction proceeds with a broad substrate scope of both coupling partners. The electron-rich, electron-poor, and ortho-/meta-/para-substituted (hetero)aryl electrophiles (e.g., Ar-OTf, Ar-I, Ar-Br, and inert Ar-Cl) all coupled well. Most of the functionalities, including aldehyde, ketone, amide, ester, nitrile, sulfone, furan, thiophene, benzothiophene, pyridine, quinolone, Ar-SiMe3, Ar-Bpin, and Ar-SnBu3, were tolerated. The dynamic nature of this method enables the direct arylation of benzylic alcohol in the presence of various nucleophilic groups, including nonactivated primary/secondary/tertiary alcohols, phenols, and free indoles. It thus offers a robust alternative to existing methods for the precise construction of diarylmethanes. The synthetic utility of the method was demonstrated by a concise synthesis of biologically active molecules and by its application to peptide modification and conjugation. Preliminary mechanistic studies revealed that the reaction of in situ formed benzyl oxalates with nickel, possibly via a radical process, is an initial step in the reaction with aryl electrophiles.