3459-14-1

Usage

Uses

Used in Pharmaceutical Research:
(3-methoxyphenyl)methanamine hydrochloride is used as a reagent for the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemical Production:
(3-methoxyphenyl)methanamine hydrochloride is utilized in the production of agrochemicals, serving as a key intermediate in the synthesis of pesticides and other agricultural chemicals to improve crop protection and yield.
Used in Organic Synthesis:
(3-methoxyphenyl)methanamine hydrochloride is employed as a versatile reagent in organic synthesis, enabling the creation of a wide range of organic compounds for various industries, including the production of fine chemicals.
Used in Chemical Research:
It is also used as a research tool in chemical laboratories to study the properties and reactions of organic amines and methoxy-containing compounds, furthering scientific understanding and innovation in the field.

Upstream product

• 1527-89-5 3-methoxybenzonitrile 
• 5071-96-5 3-METHOXYBENZYLAMINE 
• 5813-86-5 m-methoxybenzamide 
• 153903-22-1 (3-methoxy-benzyl)-carbamic acid tert-butyl ester 
• 591-31-1 3-methoxy-benzaldehyde 
• 38489-80-4 3-methoxybenzaldehyde oxime 

Downstream Products

• 128043-64-1 Ethyl 1-(3-methoxylbenzyl)-2,4,5-trioxoimidazolidine-3-acetate 
• 92764-08-4 1-(m-methoxybenzyl)imidazolidine-2,4,5-trione 
• 73604-31-6 3-hydroxybenzylamine 

Relevant academic research and scientific papers

Phosphine-Free Manganese Catalyst Enables Selective Transfer Hydrogenation of Nitriles to Primary and Secondary Amines Using Ammonia-Borane

Herein we report the synthesis of primary and secondary amines by nitrile hydrogenation, employing a borrowing hydrogenation strategy. A class of phosphine-free manganese(I) complexes bearing sulfur side arms catalyzed the reaction under mild reaction conditions, where ammonia-borane is used as the source of hydrogen. The synthetic protocol is chemodivergent, as the final product is either primary or secondary amine, which can be controlled by changing the catalyst structure and the polarity of the reaction medium. The significant advantage of this method is that the protocol operates without externally added base or other additives as well as obviates the use of high-pressure dihydrogen gas required for other nitrile hydrogenation reactions. Utilizing this method, a wide variety of primary and symmetric and asymmetric secondary amines were synthesized in high yields. A mechanistic study involving kinetic experiments and high-level DFT computations revealed that both outer-sphere dehydrogenation and inner-sphere hydrogenation were predominantly operative in the catalytic cycle.

Transition metal-free catalytic reduction of primary amides using an abnormal NHC based potassium complex: Integrating nucleophilicity with Lewis acidic activation

An abnormal N-heterocyclic carbene (aNHC) based potassium complex was used as a transition metal-free catalyst for reduction of primary amides to corresponding primary amines under ambient conditions. Only 2 mol% loading of the catalyst exhibits a broad substrate scope including aromatic, aliphatic and heterocyclic primary amides with excellent functional group tolerance. This method was applicable for reduction of chiral amides and utilized for the synthesis of pharmaceutically valuable precursors on a gram scale. During mechanistic investigation, several intermediates were isolated and characterized through spectroscopic techniques and one of the catalytic intermediates was characterized through single-crystal XRD. A well-defined catalyst and isolable intermediate along with several stoichiometric experiments, in situ NMR experiments and the DFT study helped us to sketch the mechanistic pathway for this reduction process unravelling the dual role of the catalyst involving nucleophilic activation by aNHC along with Lewis acidic activation by K ions.

Synthesis of Molybdenum Pincer Complexes and Their Application in the Catalytic Hydrogenation of Nitriles

A series of molybdenum(0), (I) and (II) complexes ligated by different PNP and NNN pincer ligands were synthesized and structurally characterized. Along with previously described Mo?PNP complexes Mo-1 and Mo-2, all prepared compounds were tested in the catalytic hydrogenation of aromatic nitriles to primary amines. Among the applied catalysts, Mo-1 is particularly well suited for the hydrogenation of electron-rich benzonitriles. Additionally, two aliphatic nitriles were transformed into the desired products in 80 and 86 percent, respectively. Moreover, catalytic intermediate Mo-1a was isolated and its role in the catalytic cycle was subsequently demonstrated.

Cobalt-based nanoparticles prepared from MOF-carbon templates as efficient hydrogenation catalysts

The development of efficient and selective nanostructured catalysts for industrially relevant hydrogenation reactions continues to be an actual goal of chemical research. In particular, the hydrogenation of nitriles and nitroarenes is of importance for the production of primary amines, which constitute essential feedstocks and key intermediates for advanced chemicals, life science molecules and materials. Herein, we report the preparation of graphene shell encapsulated Co3O4- and Co-nanoparticles supported on carbon by the template synthesis of cobalt-terephthalic acid MOF on carbon and subsequent pyrolysis. The resulting nanoparticles create stable and reusable catalysts for selective hydrogenation of functionalized and structurally diverse aromatic, heterocyclic and aliphatic nitriles, and as well as nitro compounds to primary amines (>65 examples). The synthetic and practical utility of this novel non-noble metal-based hydrogenation protocol is demonstrated by upscaling several reactions to multigram-scale and recycling of the catalyst.

Cobalt-Catalyzed and Lewis Acid-Assisted Nitrile Hydrogenation to Primary Amines: A Combined Effort

The selective hydrogenation of nitriles to primary amines using a bench-stable cobalt precatalyst under 4 atm of H2 is reported herein. The catalyst precursor was reduced in situ using NaHBEt3, and the resulting Lewis acid formed, BEt3, was found to be integral to the observed catalysis. Mechanistic insights gleaned from para-hydrogen induced polarization (PHIP) transfer NMR studies revealed that the pairwise hydrogenation of nitriles proceeded through a Co(I/III) redox process.

Sodium nitrite-catalyzed aerobic oxidative Csp2-Csp3 coupling: Direct construction of the 4-aryldihydroisoquinolinone moiety

A bioinspired approach for the construction of the 4- aryldihydroisoquinolinone moiety via direct oxidative Csp2-Csp 3 coupling has been developed, which uses inexpensive sodium nitrite as catalyst and environmentally benign oxygen in the air as terminal oxidant.

MATRIX METALLOPROTEINASE INHIBITORS AND METHODS FOR THE TREATMENT OF PAIN AND OTHER DISEASES

The present invention relates generally to bis-amide containing MMP inhibiting compounds, and more particularly to selectively deuterated bis-amide MMP-13 inhibiting compounds that exhibit increased stability or potency in relation to currently known MMP-

TBAF-catalyzed hydrosilylation for the reduction of aromatic nitriles

The selective catalytic hydrosilylation of functional groups is becoming an interesting tool for organic synthesis. In the present study, fluoride-catalyzed hydrosilylations of aromatic nitriles have been examined in detail. Using catalytic amounts of inexpensive tetra-n-butylammonium fluoride (TBAF) various aromatic nitriles are reduced in good yields under mild conditions.