1656-94-6

Usage

Uses

Used in Coordination Chemistry:
3,3'-DIPICOLYLAMINE is used as a ligand for forming coordination complexes with metal ions, particularly transition metals like cobalt and copper, due to its ability to chelate these ions effectively.
Used in Chemical Analysis:
3,3'-DIPICOLYLAMINE is utilized as a reagent or a component in analytical methods, leveraging its coordination properties to detect or quantify specific metal ions in various samples.
Used in Catalysis:
In the field of catalysis, 3,3'-DIPICOLYLAMINE is employed as a catalyst or a catalyst precursor, enhancing the efficiency of chemical reactions through its interaction with metal ions.
Used in Organic Synthesis:
3,3'-DIPICOLYLAMINE is used as a building block in the synthesis of various organic compounds, contributing to the development of new molecules with potential applications in different industries.
Used in Biological Imaging and Detection:
3,3'-DIPICOLYLAMINE is used as a contrast agent or a component in probes for biological imaging and detection, taking advantage of its coordination properties to bind with metal ions in biological systems for enhanced imaging or detection capabilities.
Used in Pharmaceutical Industry:
3,3'-DIPICOLYLAMINE is used as a starting material or intermediate in the synthesis of pharmaceutical compounds, owing to its ability to form stable complexes with metal ions that can have therapeutic effects.
Used in Material Science:
3,3'-DIPICOLYLAMINE is utilized in the development of new materials with specific properties, such as metal-organic frameworks (MOFs), which have potential applications in gas storage, catalysis, and drug delivery.

InChI:InChI=1/C12H13N3/c1-3-11(7-13-5-1)9-15-10-12-4-2-6-14-8-12/h1-8,15H,9-10H2

Upstream product

• 100-54-9 pyridine-3-carbonitrile 
• 123-91-1 1,4-dioxane 
• 64-17-5 ethanol 
• 67-56-1 methanol 
• 7664-41-7 ammonia 
• 6959-48-4 3-chloromethylpyridinium chloride 
• 59-67-6 nicotinic acid 
• 3731-52-0 3-Aminomethylpyridine 
• 2038-57-5 3-Phenylpropan-1-amine 
• 110-91-8 morpholine 

Relevant academic research and scientific papers

Pd/TiO2-Photocatalyzed Self-Condensation of Primary Amines to Afford Secondary Amines at Ambient Temperature

Symmetric secondary amines were synthesized by the self-condensation of primary amines over a palladium-loaded titanium dioxide (Pd/TiO2) photocatalyst. The reactions afforded a series of secondary amines in moderate to excellent isolated yields at ambient temperature (30 °C, in cyclopentyl methyl ether). Applicability for one-pot pharmaceutical synthesis was demonstrated by a photocatalytic reaction sequence of self-condensation of an amine followed by N-alkylation of the resulting secondary amine with an alcohol.

Hydrogenation of heteroaromatic nitriles and aromatic dinitriles by heterogeneous or homogeneous ruthenium catalysts derived from [Ru3(CO)12]

The use of the complex [Ru3(CO)12] (1) as a catalyst precursor (0.1?mol%) at 200?°C, 60?psi of H2, along with triphenylphosphine (TPP) generated ruthenium nanoparticles (Ru-Nps); this occurred in the presence of pyridine-nitriles leading to a variety of hydrogenation (secondary amine, imine, or imidazole) products, depending of the pyridine-nitrile used, under similar reaction conditions. This relates to relatively good to modest yields, determined by the substituents in the corresponding pyridine. In sharp contrast, the use of aromatic dinitriles did not generate Ru-Nps at 140?°C, 150?psi of H2 and TPP, but allowed the homogeneous catalytic hydrogenation of the 1,4- and 1,3-dicyanobenzenes, to yield the corresponding CN-substituted secondary amine or imine. The main products were characterized by different analytical methods and spectroscopic techniques.

Nano-sized La0.5Ca0.5CoO3-mediated reduction by nabh4 of aryl nitriles to bis-(benzyl) amines

Nano-sized La0.5Ca0.5CoO3 perovskite, which was produced via the sol-gel method, was an efficient heterogeneous catalyst in combination with NaBH4 for the rapid chemoselective reduction of aryl nitriles to bis-(benzyl)amines at 40°C in good to excellent yields. The physico-chemical properties of the catalyst were characterized by means of differential thermal analysis (DTA), thermogravimetric analysis (TGA), X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning electron microscopy (SEM), energy dispersive spectroscopy (EDX) and particle size distributions images. The results show that nanoparticles have regular shapes with well-defined crystal faces with an average size of 30 nm.

Heterogeneously catalyzed self-condensation of primary amines to secondary amines by supported copper catalysts

Self-condensation of primary amines to symmetrically substituted secondary amines could efficiently be promoted by an inexpensive supported copper catalyst, Cu/Al2O3, easily prepared by the reduction of the hydroxide precursor, Cu(OH)x/Al2O3. Various kinds of structurally diverse primary amines including benzylamine, picolylamine, and aliphatic amine derivatives could selectively be converted into the corresponding secondary amines in moderate to excellent yields without any cocatalysts such as bases and stabilizing ligands in 1 atm of Ar or H 2. The reactions in H2 showed higher selectivities to desired secondary amines than those in Ar. The roles of H2 are the promotion of hydrogenation of N-alkylimines and the stabilization of active Cu(0) species. In addition, in the presence of Cu/Al2O3, unsymmetrically substituted secondary amines could efficiently be synthesized by N-alkylation of primary amines with alcohols and reductive amination of aldehydes. The observed catalysis was truly heterogeneous, and the retrieved Cu/Al2O3 catalyst could be reused for self-condensation without a significant loss of its catalytic performance. The reaction mechanism involving dehydrogenation of primary amines and condensation to N-alkylimines followed by hydrogenation, the so-called "borrowing hydrogen pathway", has been proposed. The Royal Society of Chemistry 2013.

Selective cross-coupling of amines by alumina-supported palladium nanocluster catalysts

Al2O3-supported Pd nanoclusters with an average particle size of 1.8 nm act as a reusable catalyst for the selective cross-coupling of amines. The reaction is a structure-sensitive reaction, demanding coordinatively unsaturated Pd atoms on a metallic nanocluster. The support also affects the activity, an amphoteric oxide (Al2O 3) is most effective. The Royal Society of Chemistry.

A biomimetic electrocatalytic system for the atom-economical chemoselective synthesis of secondary amines

A facile one-pot oxidation-imine formation-reduction route to secondary amines can be achieved electrolytically from primary amines. This atom-economical 1ox-mediated sequence, leaving ammonia as the sole byproduct, allows the rapid chemoselect

Microwave-assisted synthesis of primary amine HX salts from halides and 7 M ammonia in methanol

The atom economical synthesis of hydrogen halide salts of primary amines, directly from the corresponding halides, avoids the production of significant amounts of secondary amine side products, and requires only evaporation of the solvent to access the products in yields generally greater than 90%. The procedure uses microwave irradiation in 7 M ammonia in methanol (Aldrich) at 130°C from 0.5 to 2.5h and works on a variety of alkyl halides, as well as mesylates and tosylates. Benzylamines are obtained from benzyl halides without significant amounts of the secondary amine side products that result without microwave heating. Direct isolation of even highly volatile primary amines as their hydrogen halide salts makes the method ideal for use in parallel synthesis.