189440-33-3

Basic information

• Product Name: 1,2-Ethanediamine, N,N-bis(2-pyridinylmethyl)-
• CAS NO: 189440-33-3
• Molecular Formula: C14H18N4
• Molecular Weight: 242.324
• Mol File: 189440-33-3.mol
• Article Data: 38

Chemical Properties

• CAS DataBase Reference: 1,2-Ethanediamine, N,N-bis(2-pyridinylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Ethanediamine, N,N-bis(2-pyridinylmethyl)-(189440-33-3)
• EPA Substance Registry System: 1,2-Ethanediamine, N,N-bis(2-pyridinylmethyl)-(189440-33-3)

Safety Data

• Hazardous Substances Data: 189440-33-3(Hazardous Substances Data)

Usage

General Description

1,2-Ethanediamine, N,N-bis(2-pyridinylmethyl)- is a chemical compound with the molecular formula C14H18N4. It is commonly referred to as BIPM and is a diamine derivative of ethylene. BIPM is a bidentate ligand, meaning it can form coordination complexes with metal ions, particularly transition metals. 1,2-Ethanediamine, N,N-bis(2-pyridinylmethyl)- is often used in coordination chemistry and can be found in various research and industrial applications, including catalysis and molecular recognition. Its ability to form stable complexes with metal ions makes it useful in the development of new materials and chemical processes. Additionally, it has potential applications in the fields of pharmacology and medicine as a chelating agent for metal-based drugs.

Upstream product

• 189440-35-5 2-(2-(bis((pyridin-2-yl)methyl)amino)ethyl)isoindoline-1,3-dione 
• 574-98-1 2-(2-bromoethyl)isoindoline-1,3-dione 
• 1539-42-0 bis[(2-pyridyl)methyl]amine 
• 2576-47-8 2-bromoethylamine hydrobromide 
• 6959-47-3 2-chloromethylpyridine hydrochloride 
• 1192597-09-3 2-azido-N,N-bis((pyridin-2-yl)methyl)ethanamine 
• 31106-82-8 2-(bromomethyl)pyridine hydrobromide 
• 119715-60-5 (E)-1-(pyridine-2-yl)-N-(pyridine-2-ylmethylene)methaneamine 
• 3731-51-9 2-(Aminomethyl)pyridine 
• 1121-60-4 pyridine-2-carbaldehyde 
• 540470-07-3 (N-tosyl-2-aminoethyl)bis(2-picolyl)amine 
• 573967-89-2 N-acetyl-N',N'-bis[(2-pyridyl)methyl]ethylenediamine 
• 383421-85-0 N-(tert-butyloxycarbonyl)-N',N'-[bis(2-pyridilmethyl)ethane-1,2-diamine] 

Downstream Products

• 436854-49-8 N-[2-(bis-pyridin-2-ylmethyl-amino)-ethyl]-2-hydroxy-benzamide 
• 222016-72-0 N,N-bis(2-pyridylmethyl)-N'-(2-hydroxybenzyl)ethane-1,2-diamine 
• 935688-07-6 ((C₅H₄NCH₂)2NCH₂CH₂N)2(CO)4C₆H₂C₄H₂ 
• 1007394-14-0 N¹-(7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)-N²,N²-bis(pyridin-2-ylmethyl)ethane-1,2-diamine 
• 573967-80-3 [Cu((2-aminoethyl)bis(2-pyridylmethyl)amine)Cl]ClO₄ 
• 674301-93-0 [Co(N,N-bis(2-pyridylmethyl)-1,2-ethanediamine)(NO₂)2](NO₃) monohydrate 
• 918942-65-1 [bromo(tetrachlorocatecholate)(N-acetyl-N',N'-bis[(2-pyridyl)methyl]ethylenediamine)iron(III)] 
• 918942-67-3 (μ-oxo)di[(N-acetyl-N',N'-bis[(2-pyridyl)methyl]ethylenediamine)iron(III)] 
• 1218934-50-9 C₄₄H₄₆N₈ 
• 220859-93-8 C₂₉H₂₈N₄ 
• 1227512-78-8 C₆H₄(CH₂N(CH₂CH₂C₇H₄N₂CH₃)2)(CHNCH₂CH₂N(CH₂C₅H₄N)2) 
• 1227512-79-9 C₃₆H₃₈N₈ 
• 1208228-06-1 ethyl N-(2-(bis(pyridin-2-ylmethyl)amino)ethyl)-N-(pyridin-2-ylmethyl)glycinate 
• 1403685-62-0 C₄₀H₄₅N₅O₄ 

Relevant articles and documents

Synthesis and characterization of copper complexes with tripodal ligands bearing amino acid groups

The tripodal ligand (2-aminoethyl)bis(2-pyridylmethyl)amine (uns-penp), known for its Cu/O2 intermediates, was modified at one side arm by a selection of amino acids. With L-Tyrosine (Tyr), L-Histidine (His) and L-Lysine (Lys) it was possible to introduce chirality into the tripodal ligand system and to investigate the corresponding copper(I) complexes [Cu{L-His(BPh3)uns-penp}], [Cu(L-Lys)uns-penp]OTf and [Cu(L-Tyr)uns-penp]OTf. [Cu{L-His(BPh3)uns-penp}] could be structurally characterized and represents the first example of a copper(I) complex with a coordinated imidazole ring of the histidine ligand. Furthermore, these complexes demonstrated catalytic activity for the oxygenation of thioanisole with hydrogen peroxide as an oxidant.

Unusual Recognition and Separation of Hydrated Metal Sulfates [M2(μ-SO4)2(H2O)n, M = ZnII, CdII, CoII, MnII] by a Ditopic Receptor

A ditopic receptor L1, having metal binding bis(2-picolyl) donor and anion binding urea group, is synthesized and explored toward metal sulfate recognition via formation of dinuclear assembly, (L1)2M2(SO4)2. Mass spectrometric analysis, 1H-DOSY NMR, and crystal structure analysis reveal the existence of a dinuclear assembly of MSO4 with two units of L1. 1H NMR study reveals significant downfield chemical shift of -NH protons of urea moiety of L1 selectively with metal sulfates (e.g., ZnSO4, CdSO4) due to second-sphere interactions of sulfate with the urea moiety. Variable-temperature 1H NMR studies suggest the presence of intramolecular hydrogen bonding interaction toward metal sulfate recognition in solution state, whereas intermolecular H-bonding interactions are observed in solid state. In contrast, anions in their tetrabutylammonium salts fail to interact with the urea -NH probably due to poor acidity of the tertiary butyl urea group of L1. Metal sulfate binding selectivity in solution is further supported by isothermal titration calorimetric studies of L1 with different Zn salts in dimethyl sulfoxide (DMSO), where a binding affinity is observed for ZnSO4 (Ka = 1.23 × 106), which is 30- to 50-fold higher than other Zn salts having other counteranions in DMSO. Sulfate salts of CdII/CoII also exhibit binding constants in the order of ～1 × 106 as in the case of ZnSO4. Positive role of the urea unit in the selectivity is confirmed by studying a model ligand L2, which is devoid of anion recognition urea unit. Structural characterization of four MSO4 [M = ZnII, CdII, CoII, MnII] complexes of L1, that is, complex 1, [(L1)2(Zn)2(μ-SO4)2]; complex 2, [(L1)2(H2O)2(Cd)2(μ-SO4)2]; complex 3, [(L1)2(H2O)2(Co)2(μ-SO4)2]; and complex 4, [(L1)2(H2O)2(Mn)2(μ-SO4)2], reveal the formation of sulfate-bridged eight-membered crownlike binuclear complexes, similar to one of the concentration-dependent dimeric forms of MSO4 as observed in solid state. Finally, L1 is found to be highly efficient in removing ZnSO4 from both aqueous and semiaqueous medium as complex 1 in the presence of other competing ZnII salts via precipitation through crystallization. Powder X-ray diffraction analysis has also confirmed bulk purity of complex 1 obtained from the above competitive crystallization experiment.

A family of structural and functional models for the active site of a unique dioxygenase: Acireductone dioxygenase (ARD)

We report the synthesis and biomimetic activity of a family of model complexes with relevance to acireductone dioxygenase (ARD), an enzyme that displays dual function based on metal identity found in the methionine salvage pathway (MSP). Three complexes with related structural motifs were synthesized and characterized derived from phenolate, and pyridine N4O Schiff-base ligands. They display pseudo-octahedral Ni(II)-N4O ligand coordination with water at the sixth site, in close alignment to the structure in the resting state of ARD. The three featured complexes exhibit carbon?carbon bond cleavage activation of lithium acetylacetonate, which was used as a model enzyme substrate. Computationally derived mechanistic routes for the observed reactivity consistent with experimental conditions are herein proposed. The mechanism suggests the possibility of Ni(II)-substrate interactions, followed by oxygen insertion. These results constitute only the third functional model system of ARD, in an attempt to further advance biomimetic contributions to the ongoing debate of ARD's unique metal mediated, regioselective oxidative cleavage.

Real-time Tracking and Sensing of Cu+ and Cu2+ with a Single SERS Probe in the Live Brain: Toward Understanding Why Copper Ions Were Increased upon Ischemia

The imbalance of Cu+ and Cu2+ in the brain is closely related to neurodegenerative diseases. However, it still lacks of effective analytical methods for simultaneously determining the concentrations of Cu+ and Cu2+. Herein, we created a novel SERS probe (CuSP) to real-time track and accurately quantify extracellular concentrations of Cu+ and Cu2+ in the live brain. The present CuSP probe demonstrated specific ability for recognition of Cu+ and Cu2+ in a dual-recognition mode. Then, a microarray consisting of 8 CuSP probes with high tempo-spatial resolution and good accuracy was constructed for tracking and simultaneously biosensing of Cu+ and Cu2+ in the cerebral cortex of living brain. Using our powerful tool, it was found that that the concentrations of Cu2+ and Cu+ were increased by ≈4.26 and ≈1.80 times upon ischemia, respectively. Three routes were first discovered for understanding the mechanisms of the increased concentrations of Cu+ and Cu2+ during ischemia.

MITOCHONDRIAL COPPER DEPLETION REPROGRAMS THE METABOLISM OF TRIPLE NEGATIVE BREAST CANCER

Provided is a mitochondrial copper depleting strategy that exploits the potential vulnerability for this metabolic by cancer cells such as Triple Negative Breast Cancer cells. A nanoparticle is provided that comprises a self-reporting copper-depleting moiety (CDM) embedded in or on the matrix comprising a semi-conducting polymer and a phospholipid-polyethylene glycol (PEG). The positively charged copper-depleting complex targets mitochondria and deprives cytochrome c oxidase of its necessary copper co-factor. Inhibition of the electron transport chain complex IV compromises oxygen consumption and abrogates fatty acid oxidation, resulting in energy deficiency induced apoptosis of the targeted cancer cells. The copper-depleting nanoparticle can report the copper depleting status through multimodal optical signal changes while decreasing the copper level in tumors to inhibit tumor growth with low toxicity and significantly prolonged survival.