92495-54-0

Basic information

• Product Name: 4'-METHOXY-2-METHYL-BIPHENYL
• Synonyms: 4'-METHOXY-2-METHYL-BIPHENYL;4-METHOXY-2'-METHYL-1,1'-BIPHENYL;AKOS BAR-1281;Anisole, p-(o-tolyl)- (7CI);4-o-Tolylanisole
• CAS NO: 92495-54-0
• Molecular Formula: C₁₄H₁₄O
• Molecular Weight: 198.26
• Mol File: 92495-54-0.mol
• Article Data: 32

Chemical Properties

• Melting Point: 97.8-98.6℃
• Boiling Point: 140-141.5℃ (13 Torr)
• Appearance: /
• CAS DataBase Reference: 4'-METHOXY-2-METHYL-BIPHENYL(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-METHOXY-2-METHYL-BIPHENYL(92495-54-0)
• EPA Substance Registry System: 4'-METHOXY-2-METHYL-BIPHENYL(92495-54-0)

Safety Data

• Hazardous Substances Data: 92495-54-0(Hazardous Substances Data)

Usage

Synthesis

Open to the atmosphere, 4-bromoanisole (1.87 g, 10 mmol), o-tolylboronic acid (1.50 g, 11 mmol), KF (spray dried, dried in an oven overnight prior to use, 1.92 g, 33 mmol), and THF (10 mL) were added to a 100-ml round-bottomed Schlenk flflask equipped with a stir bar. The reaction system was flflushed with argon for about 5 min. P(t-Bu)3 (1.9 × 10–4 M stock solution in THF; 2.31 mL, 5.0 × 10–5 mmol) and Pd2(dba)3 (2.16 × 10–5 M stock solution in THF; 2.31 mL, 5.0 × 10–5 mmol) in THF were added sequentially. After 48 h at room temperature, the reaction mixture was diluted with ether or EtOAc, fifiltered through a pad of silica gel with copious washings, and then concentrated. The crude product was then purifified via column chromatography eluting with 5% ether in hexane to yield 1.94 g (98%) of 4-methoxy-2′-methylbiphenyl as a colorless liquid.

Upstream product

• 95-46-5 2-methylphenyl bromide 
• 33397-21-6 tris(4-methoxyphenyl)bismuth 
• 1144-13-4 naphthalen-1-yl N,N-dimethylsulfamate 
• 5720-07-0 4-methoxyphenylboronic acid 
• 104-94-9 4-methoxy-aniline 
• 108-88-3 toluene 
• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 
• 100-59-4 phenylmagnesium chloride 
• 1432-38-8 (p-methoxyphenyl)dimethylsilane 
• 932-31-0 ortho-tolylmagnesium bromide 
• 623-12-1 4-chloromethoxybenzene 
• 459-60-9 1-fluoro-4-methoxybenzene 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 696-62-8 para-iodoanisole 

Downstream Products

• 103594-14-5 1-Methyl-2-(1,4,4-trimethoxy-cyclohexa-2,5-dienyl)-benzene 
• 68623-29-0 4'-Methoxy-2-((Z)-styryl)-biphenyl 
• 68623-30-3 4'-Methoxy-2-((E)-styryl)-biphenyl 
• 68623-36-9 2-methoxy-10-phenyl-9,10-dihydrophenanthrene 
• 18110-71-9 4'-methoxybiphenyl-2-carboxylic acid 

Relevant articles and documents

Synthesis of Biaryls via Decarbonylative Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling of Aryl Anhydrides

Transition metal-catalyzed cross-couplings have been widely employed in the synthesis of many important molecules in synthetic chemistry for the construction of diverse C-C bonds. Conventional cross-coupling reactions require active electrophilic coupling partners, such as organohalides or sulfonates, which are not environmentally friendly enough. Herein, we disclose the first nickel-catalyzed Suzuki-Miyaura cross-coupling of aryl anhydrides and arylboronic acids for the synthesis of biaryls in a decarbonylation manner. The reaction tolerates a wide range of electron-withdrawing, electron-neutral, and electron-donating substituents in this process.

Urea-based organocatalyst catalyzed direct C–H bond arylations of unactivated arenes

A simple 1,3-diethylurea was demonstrated to catalyze transition-metal-free arylations of unactivated aromatic C–H bonds with aryl iodides in the presence of t-BuOK. A broad range of aryl iodides with different arenes could couple in moderate to excellent yields. The mechanistic experiment results indicated that the radical is involved in this transformation.

Amide-ligand-controlled highly para-selective arylation of monosubstituted simple arenes with arylboronic acids

Pd-catalyzed highly para-selective arylations of monosubstituted simple arenes with arylboronic acids to widely existed biaryls have been developed. Inspired by requisite amide-directing groups in reported selective oxidative couplings, amide ligands, especially DMF, are designed and found to be critical for the selectivity control in current arylations.