5291-46-3

Usage

Chemical compound

Benzenemethanimine, 4-methoxy-a-phenyl-

Also known as

4-methoxybenzylamine

Molar mass

137.18 g/mol
Commonly used as a building block in organic synthesis and pharmaceutical research
Potential applications in the synthesis of various pharmaceuticals and agrochemicals

Physical state

pale yellow liquid at room temperature

Solubility

soluble in organic solvents
Importance of handling with care and following proper safety protocols in a laboratory setting

Upstream product

• 60-29-7 diethyl ether 
• 622-73-1 4-methoxybenzaldehydephenylhydrazone 
• 611-94-9 4-Methoxybenzophenone 
• 100-59-4 phenylmagnesium chloride 
• 874-90-8 4-methoxybenzonitrile 
• 100-58-3 phenylmagnesium bromide 
• 591-51-5 phenyllithium 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 100-47-0 benzonitrile 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 588-64-7 benzaldehyde phenylhydrazone 

Downstream Products

• 143678-01-7 2-p-anisyl-2,4,5-triphenyl-2H-imidazole N-oxide 
• 5291-47-4 4-methoxy-benzophenone-imine; hydrochloride 
• 51250-42-1 p-Methoxyphenyl-phenylchlormethylisocyanat 
• 1221958-17-3 5-methoxy-1,2,3-triphenyl-1H-inden-1-ylamine 
• 1221958-19-5 1-(4-methoxyphenyl)-2,3-diphenyl-1H-inden-1-ylamine 
• 611-94-9 4-Methoxybenzophenone 
• 2538-34-3 4-methoxybenzhydrylamine 

Relevant academic research and scientific papers

Copper-catalyzed [2+3]-annulation of N-H imines with vinyl azides: Access to polyaryl 2: H -imidazoles

A practical method for the synthesis of 2H-imidazoles via a [2+3] annulation of N-H imines with vinyl azides using a copper catalyst is developed. In this conversion, environmentally friendly oxygen is used as the sole oxidant and N2 and H2O are the only by-products. The catalytic transformation, operating under mild conditions, is operationally simple and is considered as a readily available catalytic system having good substrate and functional compatibility with high atom-efficiency without the need for additional ligands or additives.

Hydrogen bond directed aerobic oxidation of amines via photoredox catalysis

An application of H-bonding interactions for directing the α-C-H oxidation of amines to amides and amino-ketones catalyzed by an organic photocatalyst is reported. The high efficiency of this method is demonstrated by the aerobic oxidation of pyrrolidines, diarylamines and benzylamines bearing urea groups with high yields and a wide substrate scope.

Introducing Glycerol as a Sustainable Solvent to Organolithium Chemistry: Ultrafast Chemoselective Addition of Aryllithium Reagents to Nitriles under Air and at Ambient Temperature

Edging closer towards developing air and moisture compatible polar organometallic chemistry, the chemoselective and ultrafast addition of a range of aryllithium reagents to nitriles has been accomplished by using glycerol as a solvent, at ambient temperature in the presence of air, establishing a novel sustainable access to aromatic ketones. Addition reactions occur heterogeneously (“on glycerol conditions”), where the lack of solubility of the nitriles in glycerol and the ability of the latter to form strong intermolecular hydrogen bonds seem key to favouring nucleophilic addition over competitive hydrolysis. Remarkably, PhLi exhibits a greater resistance to hydrolysis working “on glycerol” conditions than “on water”. Introducing glycerol as a new solvent in organolithium chemistry unlocks a myriad of opportunities for developing more sustainable, air and moisture tolerant main-group-metal-mediated organic synthesis.

Synthesis and properties of geometrical 4-diarylmethylene analogs of the green fluorescent protein chromophore

We have developed a novel analog of the GFP chromophore: geo-DAIN. Since geo-DAIN is equipped with an E/Z-photoisomerizable geometrical diarylmethylene moiety instead of benzylidene of the GFP chromophore, different-colored reversible emissions are expected. We synthesized geo-DAIN by a condensation with methyl imidate and N-(diarylmethylene)glycinate. We found the emission from geo-DAIN to be different from that of benzylidene-type analogs; in the powder state, the E- and Z-isomers of geo-DAIN emitted different fluorescence colors.

Efficient and scalable synthesis of ketones via nucleophilic Grignard addition to nitriles using continuous flow chemistry

In the present Letter we report the development of efficient continuous flow chemistry conditions for the scalable preparation of ketones. This transformation is achieved via nucleophilic addition of Grignard reagents to the corresponding nitriles and imine hydrolysis by means of in-series plug flow reactors.

Nickel catalyzed cross-coupling and amination reactions of aryl nitriles

Aryl nitriles have been found to participate in cross-coupling and amination reactions via nickel-catalyzed activation of the C-CN bond. With the development of these synthetically useful transformations, aryl nitriles can now be considered along with ary

C-C bond activation with selective functionalization: Preparation of unsymmetrical biaryls from benzonitriles

For the first time, benzonitriles have been shown to participate in metal-catalyzed cross coupling reactions via activation of the C-CN bond. Thus, reaction of a benzonitrile with an aryl Grignard derivative in the presence of a Ni catalyst can readily pr

KETIMINES FROM KETONES AND AMMONIA

The direct synthesis of ketimines from ammonia and ketones catalyzed by ammonium chloride is described.