53039-51-3

Basic information

• Product Name: Benzene, 1-[(4-methoxyphenyl)methyl]-3-methyl-
• CAS NO: 53039-51-3
• Molecular Formula: C15H16O
• Molecular Weight: 212.291
• Mol File: 53039-51-3.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: Benzene, 1-[(4-methoxyphenyl)methyl]-3-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-[(4-methoxyphenyl)methyl]-3-methyl-(53039-51-3)
• EPA Substance Registry System: Benzene, 1-[(4-methoxyphenyl)methyl]-3-methyl-(53039-51-3)

Safety Data

• Hazardous Substances Data: 53039-51-3(Hazardous Substances Data)

Upstream product

• 14503-41-4 m-methylbenzyl tosylate 
• 5720-07-0 4-methoxyphenylboronic acid 
• 620-19-9 1-chloromethyl-3-methyl-benzene 
• 615-37-2 ortho-methylphenyl iodide 
• 625-95-6 3-Iodotoluene 
• 122-84-9 4-methoxybenzyl methyl ketone 
• 352-70-5 m-Fluorotoluene 
• 161200-66-4 (4-MeOC₆H₄CH₂)Ti(O-i-Pr)3 
• 104-93-8 p-methylanizole 
• 591-17-3 meta-bromotoluene 
• 620-13-3 1-bromomethyl-3-methyl-benzene 
• 16605-27-9 3-methylbenzyl N,N-dimethylcarbamate 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 62381-20-8 2-(3-methylphenyl)-1,3-dithiane 

Relevant articles and documents

Palladium-catalyzed cross-coupling of benzyltitanium(IV) reagents with aryl fluorides

The first palladium-catalyzed cross-coupling between benzyltitanium(IV) reagents with aryl fluorides is reported. A variety of diarylmethanes can be prepared in good to excellent yields by the catalyst system of PdCl2(dppf)2 associated with 1-[2-(di-tert-butylphosphanyl)phenyl]-4-methoxypiperidine. This reaction offered a highly efficient approach to diarylmethanes that are commonly found in life-changing drug molecules. Graphical abstract: [Figure not available: see fulltext.]

Transition-Metal-Free Synthesis of Biarylmethanes from Aryl Iodides and Benzylic Ketones

An original metal-free procedure for the synthesis of biarylmethanes is disclosed herein. The reactions occur with high selectivity starting from aryl iodides and benzylic ketones in the presence of superbasic media (CsOH/DMSO). This procedure allows a straightforward access to a wide range of biarylmethane derivatives substituted with electron-withdrawing and -donating substituents.

Transition-Metal-Free Suzuki-Type Cross-Coupling Reaction of Benzyl Halides and Boronic Acids via 1,2-Metalate Shift

Cross-coupling of organoboron compounds with electrophiles (Suzuki-Miyaura reaction) has greatly advanced C-C bond formation and has been well received in medicinal chemistry. During the past 50 years, transition metals have played a central role throughout the catalytic cycle of this important transformation. In this process, chemoselectivity among multiple carbon-halogen bonds is a common challenge. In particular, selective oxidative addition of transition metals to alkyl halides rather than aryl halides is difficult due to unfavorable transition states and bond strengths. We describe a new approach that uses a single organic sulfide catalyst to activate both C(sp3) halides and arylboronic acids via a zwitterionic boron "ate" intermediate. This "ate" species undergoes a 1,2-metalate shift to afford Suzuki coupling products using benzyl chlorides and arylboronic acids. Various diaryl methane analogues can be prepared, including those with complex and biologically active motifs. The reactions proceed under transition-metal-free conditions, and C(sp2) halides, including aryl bromides and iodides, are unaffected. The orthogonal chemoselectivity is demonstrated in the streamlined synthesis of highly functionalized diaryl methane scaffolds using multi-halogenated substrates. Preliminary mechanistic experiments suggest both the sulfonium salt and the sulfur ylide are involved in the reaction, with the formation of sulfonium salt being the slowest step in the overall catalytic cycle.