39642-65-4

Usage

Chemical compound

1,3-bis(3-pyridylmethyl)urea is a chemical compound used as a ligand in coordination chemistry.

Physical appearance

It is a white solid.

Solubility

Insoluble in water but soluble in organic solvents.

Complex formation

Known for its ability to form stable complexes with metal ions, particularly transition metals like copper and nickel.

Applications in catalysis

These complexes have been studied for their potential applications in catalysis.

Building blocks

They are also considered as building blocks for coordination polymers.

Medicinal chemistry

1,3-bis(3-pyridylmethyl)urea has been investigated for its potential use in medicinal chemistry.

Chelating agent

Specifically, it has been studied as a chelating agent for metal-based drugs.

Versatile applications

The compound has versatile applications in the fields of chemistry, catalysis, and drug development.

InChI:InChI=1/C13H14N4O/c18-13(16-9-11-3-1-5-14-7-11)17-10-12-4-2-6-15-8-12/h1-8H,9-10H2,(H2,16,17,18)

Upstream product

• 102-09-0 bis(phenyl) carbonate 
• 3731-52-0 3-Aminomethylpyridine 
• 124-38-9 carbon dioxide 
• 201230-82-2 carbon monoxide 
• 68-12-2 N,N-dimethyl-formamide 
• 67-56-1 methanol 
• 530-62-1 1,1'-carbonyldiimidazole 

Relevant academic research and scientific papers

Equipping metallo-supramolecular macrocycles with functional groups: Assemblies of pyridine-substituted urea ligands

A series of di-(m-pyridyl)-urea ligands were prepared and characterized with respect to their conformations by NOESY experiments and crystallography. Methyl substitution in different positions of the pyridine rings provides control over the position of the pyridine N atoms relative to the urea carbonyl group. The ligands were used to self-assemble metallo-supramolecular M 2L2 and M3L3 macrocycles which are generated in a finely balanced equilibrium in DMSO and DMF according to DOSY NMR experiments and ESI FTICR mass spectrometry. Again, crystallography was used to characterize the assemblies. Methyl substitution in positions next to the pyridine nitrogen prevents coordination, while the other ligands form small metallo-supramolecular macrocycles. The incorporated urea carbonyl groups provide hydrogen bonding sites which converge towards the center of the assemblies. The Royal Society of Chemistry 2012.

Palladium-Catalyzed Aerobic Oxidative Carbonylation of Amines Enables the Synthesis of Unsymmetrical N,N′-Disubstituted Ureas

A ligand-free palladium-catalyzed aerobic oxidative carbonylation of amines for the synthesis of ureas, particular unsymmetrically N,N′-disubstituted ureas, which cannot be accessed by any other palladium-catalyzed oxidative carbonylation of amines to date, is presented. An array of symmetrical and unsymmetrical ureas were straightforwardly synthesized by using inexpensive, readily available, stable, and safe amines with good to excellent yields under a pressure of 1 atm. This novel method employs oxygen as the sole oxidant and offers an attractive alternative to transition-metal-based oxidant systems.

PYRIDINIUM COMPOUNDS, A SYNTHESIS METHOD THEREFOR, METAL OR METAL ALLOY PLATING BATHS CONTAINING SAID PYRIDINIUM COMPOUNDS AND A METHOD FOR USE OF SAID METAL OR METAL ALLOY PLATING BATHS

The present invention concerns pyridinium compounds, a synthesis method for their preparation, metal or metal alloy plating baths containing said pyridinium compounds and a method for use of said metal or metal alloy plating baths. The plating baths are particularly suitable for use in filling of recessed structures in the electronics and semiconductor industry including dual damascene applications.

Ruthenium-Catalyzed Urea Synthesis by N-H Activation of Amines

Activation of the N-H bond of amines by a ruthenium pincer complex operating via amine-amide metal-ligand cooperation is demonstrated. Catalytic formyl C-H activation of N,N-dimethylformamide (DMF) is observed in situ, which resulted in the formation of CO and dimethylamine. The scope of this new mode of bond activation is extended to the synthesis of urea derivatives from amines using DMF as a carbon monoxide (CO) surrogate. This catalytic protocol allows the synthesis of simple and functionalized urea derivatives with liberation of hydrogen, devoid of any stoichiometric activating reagents, and avoids the direct use of fatal CO. The catalytic carbonylation occurred at low temperature to provide the formamide; a formamide intermediate was isolated. The consecutive addition of different amines provided unsymmetrical urea compounds. The reactions are proposed to proceed via N-H activation of amines followed by CO insertion from DMF and with liberation of dihydrogen.

Ruthenium-Catalyzed Urea Synthesis Using Methanol as the C1 Source

An unprecedented protocol for urea synthesis directly from methanol and amine was accomplished. The reaction is highly atom-economical, producing hydrogen as the sole byproduct. Commercially available ruthenium pincer complexes were used as catalysts. In addition, no additive, such as a base, oxidant, or hydrogen acceptor, was required. Furthermore, unsymmetrical urea derivatives were successfully obtained via a one-pot, two-step reaction.

Selective N-methylation of aliphatic amines with CO2 and hydrosilanes using nickel-phosphine catalysts

A method using CO2 and PhSiH3 for the methylation of primary and secondary aliphatic amines catalyzed by Ni (0) complexes was developed, selectively producing the monomethylated products in moderate to good yields. For that purpose, two catalysts were used: [(dippe)Ni(μ-H)]2 and the commercially available Ni(COD)2/dcype, both of which were rather efficient in this process. With a slight experimental modification, the reaction allowed the production of monomethylated ureas in good yields by using low amounts of PhSiH3. On the basis of the experimental results, we propose a possible reaction mechanism for the formation of the new C-N bond.