104-84-7

Usage

Uses

Used in Pharmaceutical Industry:
Benzenemethanamine,4-methylis used as a building block in the synthesis of various bioactive compounds, such as anticonvulsants, for their potential therapeutic applications.
Used in Food Industry:
Benzenemethanamine,4-methylis used to stimulate food consumption and counteract the appetite-suppressing effects of amphetamine, acting on brain Shaker-like Kv1.1 channels.
Used in Analytical Chemistry:
Benzenemethanamine,4-methylis used as a background electrolyte in ethanol/water solution (1:4) for the determination of individual compounds in capillary zone electrophoresis with indirect detection at 210 nm.
Used in Organic Synthesis:
Benzenemethanamine,4-methylis used as a building block in the synthesis of benzimidazoles, along with 4-chlorophenyl isothiocyanate, for the development of new chemical compounds.

InChI:InChI=1/C8H11N/c1-7-2-4-8(6-9)5-3-7/h2-5H,6,9H2,1H3/p+1

Upstream product

• 100-97-0 hexamethylenetetramine 
• 104-82-5 4-Methylbenzyl chloride 
• 540-69-2 ammonium formate 
• 104-87-0 4-methyl-benzaldehyde 
• 104-85-8 para-methylbenzonitrile 
• 25079-96-3 N-(4-methylbenzyl)acetamide 
• 827-71-4 4-methyl-benzimidic acid ethyl ester 
• 7664-93-9 sulfuric acid 
• 91012-04-3 methyl N-(4-methylbenzyl)carbamate 
• 589-18-4 4-Methylbenzyl alcohol 
• 1202873-19-5 1-methyl-4-methylamino-2,5-cyclohexadiene-1-carboxylic acid 
• 3235-02-7 p-methylbenzaldehyde oxime 
• 40739-81-9 p-tolualdehyde p-toluenesulfonylhydrazone 
• 78-81-9 isobutylamine 

Downstream Products

• 17101-98-3 (4-methyl-benzyl)carbamic acid ethyl ester 
• 41882-47-7 N-benzylidene-1-(p-tolyl)methanamine 
• 35305-46-5 N-(4-methylbenzyl)-N’-phenylurea 
• 35305-48-7 1-(4-methylbenzyl)-3-phenyl-2-thiourea 
• 71022-60-1 (E)-N-(4-methylbenzylidene)(4-methylphenyl)methanamine 
• 58015-09-1 N₁,N₂-bis(4-methylbenzyl)ethane-1,2-diamine 
• 25079-96-3 N-(4-methylbenzyl)acetamide 
• 19148-78-8 2-(4-methyl-benzyl)-benzo[d]isothiazole-3-thione 
• 41882-22-8 N-(p-Methylbenzyl)-m-chlorbenzamid 
• 41882-21-7 2-chloro-N-(4-methylbenzyl)benzamide 
• 41882-23-9 N-(p-Chlorobenzoyl)-p-methylbenzylamine 
• 26367-03-3 5-(4-methyl-benzyl)-3-phenethyl-[1,3,5]thiadiazinane-2-thione 
• 16735-75-4 1,3-bis-(4-methyl-benzyl)-thiourea 
• 33312-11-7 N,N'-bis-(4-methyl-benzyl)-3,3'-disulfanediyl-bis-propionamide 

Relevant academic research and scientific papers

Selective ruthenium-catalyzed transfer hydrogenations of nitriles to amines with 2-butanol

Transfer your hydrogen: Fast and general transfer hydrogenation of nitriles to form primary amines is possible with a homogeneous Ru/1,4- bis(diphenylphosphino)butane (DPPB) catalyst (see scheme). The use of 2-butanol as the hydrogen-transfer reagent is essential for the selective reduction of aromatic, heteroaromatic, and aliphatic nitriles with this system. Copyright

Copper catalyzed reduction of azides with diboron under mild conditions

We report herein the first Cu catalyzed reduction of azides with B2pin2 (pin = pinacolato) as the reductant under very mild conditions. A series of primary amines and amides were obtained in moderate to excellent yields with high chemoselectivity and good functional group tolerance. This reaction can be performed with a cheap copper salt, a simple NHC ligand and a diboron reagent.

Hydrogenation of Nitriles and Ketones Catalyzed by an Air-Stable Bisphosphine Mn(I) Complex

Efficient hydrogenations of nitriles and ketones with molecular hydrogen catalyzed by a well-defined bench-stable bisphosphine Mn(I) complex are described. These reactions are environmentally benign and atomically economic, implementing an inexpensive, earth-abundant nonprecious metal catalyst. A range of aromatic and aliphatic nitriles and ketones were efficiently converted into primary amines and alcohols, respectively, in good to excellent yields. The hydrogenation of nitriles proceeds at 100 °C with catalyst loading of 2 mol % and 20 mol % base (t-BuOK), while the hydrogenation of ketones takes place already at 50 °C, with a catalyst loading of 1 mol % and 5 mol % of base. In both cases, a hydrogen pressure of 50 bar was applied.

Preparation of a magnetic mesoporous Fe3O4-Pd@TiO2 photocatalyst for the efficient selective reduction of aromatic cyanides

Herein, a hierarchical magnetic mesoporous microsphere was successfully prepared as a photocatalyst via a simple and reproducible route. Typically, Pd nanoparticles (NPs) were evenly dispersed on the surface of a magnetic Fe3O4 microsphere and then coated with a porous anatase-TiO2 shell to form Fe3O4-Pd@TiO2. The core-shell structure could efficiently suppress the conglomeration of Pd NPs during the calcination process at high temperatures as well as the shedding of Pd during the catalytic reaction process in the liquid phase. The as-prepared photocatalyst was characterized by TEM, XRD, XPS, VSM, and N2 adsorption-desorption. Fe3O4-Pd@TiO2 exhibits high photocatalytic activity for the selective reduction of aromatic cyanides to aromatic primary amines in an acidic aqueous solution. Moreover, this magnetic photocatalyst could be easily recovered from the reaction mixture by an external magnet and reused five times without significant reduction in its activity. The superior photocatalytic efficiency of the proposed photocatalyst may be attributed to its high charge separation efficiency and charge transfer rate, which are caused by the Schottky junction and large interface area. The results indicate that the strategy of coating the active noble metal sites with a mesoporous semiconductor shell has a significant potential for application in metal-semiconductor-based photocatalytic reactions.

Zirconium-hydride-catalyzed site-selective hydroboration of amides for the synthesis of amines: Mechanism, scope, and application

Developing mild and efficient catalytic methods for the selective synthesis of amines is a longstanding research objective. In this respect, catalytic deoxygenative amide reduction has proven to be promising but challenging, as this approach necessitates selective C–O bond cleavage. Herein, we report the selective hydroboration of primary, secondary, and tertiary amides at room temperature catalyzed by an earth-abundant-metal catalyst, Zr-H, for accessing diverse amines. Various readily reducible functional groups, such as esters, alkynes, and alkenes, were well tolerated. Furthermore, the methodology was extended to the synthesis of bio- and drug-derived amines. Detailed mechanistic studies revealed a reaction pathway entailing aldehyde and amido complex formation via an unusual C–N bond cleavage-reformation process, followed by C–O bond cleavage.

Deoxygenative hydroboration of primary, secondary, and tertiary amides: Catalyst-free synthesis of various substituted amines

Transformation of relatively less reactive functional groups under catalyst-free conditions is an interesting aspect and requires a typical protocol. Herein, we report the synthesis of various primary, secondary, and tertiary amines through hydroboration of amides using pinacolborane under catalyst-free and solvent-free conditions. The deoxygenative hydroboration of primary and secondary amides proceeded with excellent conversions. The comparatively less reactive tertiary amides were also converted to the corresponding N,N-diamines in moderate yields under catalyst-free conditions, although alcohols were obtained as a minor product.

Cobalt-Catalyzed Hydrogenative Transformation of Nitriles

Here, we report the transformation of nitrile compounds in a hydrogen atmosphere. Catalyzed by a cobalt/tetraphosphine complex, hydrogenative coupling of unprotected indoles with nitriles proceeds smoothly in a basic medium, yielding C3 alkylated indoles. In addition, the direct hydrogenation of nitriles under the same conditions yielded primary amines. Isotope labeling experiments, along with a series of control experiments, revealed a reaction pathway that involves nucleophilic addition of indoles and 1,4-reduction of a conjugate imine intermediate. Different from reductive alkylation of indoles under an acidic condition, E1cB elimination is believed to occur in this base-promoted hydrogenative coupling reaction.

Method for preparing primary amine by catalytically reducing nitrile compounds through nano-porous palladium catalyst

The invention belongs to the technical field of heterogeneous catalysis, and provides a method for preparing primary amine by catalytically reducing nitrile compounds with a nano-porous palladium catalyst. According to the invention, aromatic and aliphatic nitrile compounds are adopted as raw materials, nano-porous palladium is adopted as a catalyst, ammonia borane is adopted as a hydrogen source, no additional additive is added, and selective hydrogenation is performed to prepare the corresponding primary amine. The method provided by the invention has the beneficial effects of mild reaction conditions, no additive, environmental protection, no need of hydrogen, simple operation, stable hydrogen source, safety, harmlessness, high conversion rate, high selectivity and good catalyst stability, and makes industrialization possible.

Reaction of Diisobutylaluminum Borohydride, a Binary Hydride, with Selected Organic Compounds Containing Representative Functional Groups

The binary hydride, diisobutylaluminum borohydride [(iBu)2AlBH4], synthesized from diisobutylaluminum hydride (DIBAL) and borane dimethyl sulfide (BMS) has shown great potential in reducing a variety of organic functional groups. This unique binary hydride, (iBu)2AlBH4, is readily synthesized, versatile, and simple to use. Aldehydes, ketones, esters, and epoxides are reduced very fast to the corresponding alcohols in essentially quantitative yields. This binary hydride can reduce tertiary amides rapidly to the corresponding amines at 25 °C in an efficient manner. Furthermore, nitriles are converted into the corresponding amines in essentially quantitative yields. These reactions occur under ambient conditions and are completed in an hour or less. The reduction products are isolated through a simple acid-base extraction and without the use of column chromatography. Further investigation showed that (iBu)2AlBH4 has the potential to be a selective hydride donor as shown through a series of competitive reactions. Similarities and differences between (iBu)2AlBH4, DIBAL, and BMS are discussed.

Metal-Organic Framework-Confined Single-Site Base-Metal Catalyst for Chemoselective Hydrodeoxygenation of Carbonyls and Alcohols

Chemoselective deoxygenation of carbonyls and alcohols using hydrogen by heterogeneous base-metal catalysts is crucial for the sustainable production of fine chemicals and biofuels. We report an aluminum metal-organic framework (DUT-5) node support cobalt(II) hydride, which is a highly chemoselective and recyclable heterogeneous catalyst for deoxygenation of a range of aromatic and aliphatic ketones, aldehydes, and primary and secondary alcohols, including biomass-derived substrates under 1 bar H2. The single-site cobalt catalyst (DUT-5-CoH) was easily prepared by postsynthetic metalation of the secondary building units (SBUs) of DUT-5 with CoCl2 followed by the reaction of NaEt3BH. X-ray photoelectron spectroscopy and X-ray absorption near-edge spectroscopy (XANES) indicated the presence of CoII and AlIII centers in DUT-5-CoH and DUT-5-Co after catalysis. The coordination environment of the cobalt center of DUT-5-Co before and after catalysis was established by extended X-ray fine structure spectroscopy (EXAFS) and density functional theory. The kinetic and computational data suggest reversible carbonyl coordination to cobalt preceding the turnover-limiting step, which involves 1,2-insertion of the coordinated carbonyl into the cobalt-hydride bond. The unique coordination environment of the cobalt ion ligated by oxo-nodes within the porous framework and the rate independency on the pressure of H2 allow the deoxygenation reactions chemoselectively under ambient hydrogen pressure.