5452-87-9

Basic information

• Product Name: NSC19005
• Synonyms: NSC19005;Methylbis(2-pyridylethyl)aMine;N-Methylbis[2-(2-pyridylethyl)]aMine;N-Methyl-N,N-bis(2-pyridylethyl)aMine;N-Methyl-N-[2-(2-pyridinyl)ethyl]-2-pyridineethanaMine;N-methyl-2-(pyridin-2-yl)-N-(2-(pyridin-2-yl)ethyl)ethanamine;Betahistine EP Impurity C
• CAS NO: 5452-87-9
• Molecular Formula: C₁₅H₁₉N₃
• Molecular Weight: 241.33146
• Product Categories: Amines;Aromatics;Heterocycles;Intermediates
• Mol File: 5452-87-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 371.9°Cat760mmHg
• Flash Point: 178.7°C
• Appearance: /
• Density: 1.067g/cm³
• Vapor Pressure: 1E-05mmHg at 25°C
• Refractive Index: 1.568
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Dichloromethane (Slightly), Ethanol (Slightly), Ethyl Ace
• PKA: 8.17±0.50(Predicted)
• CAS DataBase Reference: NSC19005(CAS DataBase Reference)
• NIST Chemistry Reference: NSC19005(5452-87-9)
• EPA Substance Registry System: NSC19005(5452-87-9)

Safety Data

• Hazardous Substances Data: 5452-87-9(Hazardous Substances Data)

Usage

Uses

N-Methyl-N,N-bis(2-pyridylethyl)amine is used as a reagent in the preparation of copper pyridylmethylethylenediamine dicyanamido polymeric complexes.

InChI:InChI=1/C15H19N3/c1-18(12-8-14-6-2-4-10-16-14)13-9-15-7-3-5-11-17-15/h2-7,10-11H,8-9,12-13H2,1H3

Downstream Products

• 100-69-6 2-vinylpyridine 
• 5638-76-6 betahistine 

Relevant articles and documents

Mechanism of aromatic hydroxylation in a copper monooxygenase model system. 1,2-methyl migrations and the NIH shift in copper chemistry

The NIH shift mechanism appears to be operative in a copper monooxygenase model system involving dicopper ion complex mediated O2 hydroxylation of an arene substrate. Previous studies have shown that when a dicopper(I) complex containing two tridentate PY2 units (PY2 = bis[2-(2-pyridyl)ethyl]amine) which are linked by a m-xylyl group, i.e., [Cu2(XYL-H)]2+ (1), is reacted with dioxygen, a Cu2O2 intermediate forms and hydroxylation in the intervening 2-xylyl position occurs. Here, corresponding reactions of 2-methyl substituted analogues [Cu2(Me2XYL-CH3)]2+ (4) and [Cu2(XYL-CH3)]2+ (5) are described in detail. Oxygenation of these causes xylyl hydroxylation reactions producing new phenol products, with concomitant 1,2-migration of the methyl group, loss of one PY2 ligand arm, and formaldehyde formation. Manometric O2 uptake experiments and an 18O2 labeling study confirm that the stoichiometry of these reactions are consistent with that observed for monooxygenases. A reaction carried out using a dinucleating ligand which has been deuterated in benzylic positions confirms that the CH2O product is derived from this carbon atom, a result also consistent with migration of the 2-methyl group. A small yield of methylbis[2-(2-pyridyl)ethyl]amine (MePY2) is consistently obtained, and experiments suggest this may be derived from the reduction of an intermediate iminium salt [CH2=N[CH2CH2PY]2]+ (PY = 2-pyridyl). The hydroxylation induced 1,2-methyl migrations observed here are reminiscent of the NIH shift reactions previously observed only in iron hydroxylases and suggest that the copper ion mediated reactions proceed by the electrophilic attack of a Cu2O2 intermediate upon the proximate aromatic substrate. A detailed mechanism is proposed and discussed in terms of the known O2 reactivity and structure of these dinuclear copper complexes. The biological relevance and significance of this monooxygenase model system is also discussed.