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Usage

Uses

Used in Pharmaceutical Research and Development:
1,2,3,4-tetrahydro-N-(4-methylphenyl)-1-Naphthalenamine serves as a key component in the research and development of pharmaceuticals, specifically in the study of neurotransmitters and receptor binding. Its unique structure allows for the exploration of its interactions with various biological targets, which is crucial for the advancement of drug discovery.
Used in Neurological and Psychiatric Disorder Treatment:
1,2,3,4-tetrahydro-N-(4-methylphenyl)-1-Naphthalenamine has been investigated for its potential role in the treatment of various neurological and psychiatric disorders. Its specific application in this field is attributed to its capacity to modulate neurotransmission and potentially influence the symptoms associated with such conditions.
Used in Medicinal Chemistry Research:
Due to its structural similarity to other biologically active compounds, 1,2,3,4-tetrahydro-N-(4-methylphenyl)-1-Naphthalenamine is a valuable tool in medicinal chemistry research. It aids in the design and synthesis of new drugs, providing insights into the structural requirements for activity against specific biological targets.
While the specific biological and pharmacological properties of 1,2,3,4-tetrahydro-N-(4-methylphenyl)-1-Naphthalenamine are still under investigation, its multifaceted applications in the pharmaceutical and chemical research domains highlight its significance. Further studies are essential to fully comprehend its potential, ensuring that its use is optimized for the development of novel therapeutic agents and research tools.

Upstream product

• 90-15-3 α-naphthol 
• 106-49-0 p-toluidine 
• 2217-40-5 1,2,3,4-tetrahydronaphthalen-1-amine 
• 106-44-5 p-cresol 
• 119-64-2 tetralin 
• 90-11-9 1-Bromonaphthalene 
• 634-43-5 N-(p-tolyl)naphthalen-1-amine 

Relevant academic research and scientific papers

Catalytic Amination of Phenols with Amines

Given the wide prevalence and ready availability of both phenols and amines, aniline synthesis through direct coupling between these starting materials would be extremely attractive. Herein, we describe a rhodium-catalyzed amination of phenols, which provides concise access to diverse anilines, with water as the sole byproduct. The arenophilic rhodium catalyst facilitates the inherently difficult keto–enol tautomerization of phenols by means of π-coordination, allowing for the subsequent dehydrative condensation with amines. We demonstrate the generality of this redox-neutral catalysis by carrying out reactions of a large array of phenols with various electronic properties and a wide variety of primary and secondary amines. Several examples of late-stage functionalization of structurally complex bioactive molecules, including pharmaceuticals, further illustrate the potential broad utility of the method.

Aluminum Hydroxide Secondary Building Units in a Metal-Organic Framework Support Earth-Abundant Metal Catalysts for Broad-Scope Organic Transformations

The intrinsic heterogeneity of alumina (Al2O3) surface presents a challenge for the development of alumina-supported single-site heterogeneous catalysts and hinders the characterization of catalytic species at the molecular level as well as the elucidation of mechanistic details of the catalytic reactions. Here we report the use of aluminum hydroxide secondary building units (SBUs) in the MIL-53(Al) metal-organic framework (MOF) with the formula Al(μ2-OH)(BDC) (BDC = 1,4-benzenedicarboxylate) as a uniform and structurally defined functional mimic of Al2O3 surface for supporting Earth-abundant metal (EAM) catalysts. The μ2-OH groups in MIL-53(Al) SBUs were readily deprotonated and metalated with CoCl2 and FeCl2 to afford MIL-53(Al)-CoCl and MIL-53(Al)-FeCl precatalysts which were characterized by powder X-ray diffraction, nitrogen sorption, elemental analysis, density functional theory, and extended X-ray fine structure spectroscopy. Activation with NaBEt3H converted MIL-53(Al)-CoCl to MIL-53(Al)-CoH which effectively catalyzed hydroboration of alkynes and nitriles and hydrosilylation of esters. X-ray photoelectron spectroscopy and X-ray absorption near-edge spectroscopy (XANES) indicated the presence of AlIII and CoII centers in MIL-53(Al)-CoH while deuterium labeling studies suggested σ-bond metathesis as a key step for the MIL-53(Al)-CoH-catalyzed addition reactions. MIL-53(Al)-FeCl competently catalyzed oxidative Csp3-H amination and Wacker-type alkene oxidation. XANES analysis revealed the oxidation of FeII to FeIII centers in the activated MIL-53(Al)-FeCl catalyst and suggested that oxidative Csp3-H amination occurs via the formation of FeIII-OtBu species by single electron transfer between FeII centers in MIL-53(Al)-FeCl and (tBuO)2 with concomitant generation of 1 equiv of tBuO· radical, C-H activation through hydrogen atom abstraction to generate alkyl radicals, protonation of FeIII-OtBu by aniline to generate MIL-53(Al)-FeIII-anilide, and finally C-N coupling between the FeIII-anilide and alkyl radical to form the Csp3-H amination product and regenerate the FeII catalyst. These highly active single-site MOF-based solid catalysts were readily recovered and reused up to five times without significant decrease in catalytic activity. This work thus demonstrates the great potential of using the aluminum hydroxide SBUs in MOFs to support EAM catalysts for important organic transformations.

Palladium-catalyzed reductive coupling of phenols with anilines and amines: efficient conversion of phenolic lignin model monomers and analogues to cyclohexylamines

Phenols, being readily available from naturally abundant lignins, are important future feedstocks for the renewable production of fuels, chemicals, and energy. Herein, a highly efficient Pd-catalyzed direct coupling of phenolic lignin model monomers and analogues with anilines to give cyclohexylamines using cheap and safe sodium formate as hydrogen donor is described. A variety of secondary and tertiary substituted cyclohexylamines can be synthesized under convenient conditions in moderate to excellent yields.

B(C6F5)3-catalyzed metal-free hydrogenation of naphthylamines

A catalytic metal-free hydrogenation of naphthylamines using B(C6F5)3 as a catalyst was successfully achieved under mild conditions for the first time to furnish a variety of tetrahydronaphthylamines in 88-99% yields.

Palladium-catalyzed asymmetric hydrogenation of simple ketimines using a Bronsted acid as activator

Using a catalytic amount of a Bronsted acid as activator of simple imines, the highly enantioselective homogeneous palladium-catalyzed asymmetric hydrogenation of simple ketimines was successfully developed with up to 95% ee.