neocuproine

Also known as DMPHEN, neocuproin, 2,9-dimethylphenanthroline, 2,9-dimethyl-o-phenanthroline

Neocuproine is a heterocyclic organic compound and chelating agent. Phenanthroline ligands were first published in the late 19th century, and the derivatives substituted at the 2 and 9 positions are among the most studied of the modified phenanthrolines.

Research

424 papers

Neocuproine as a Redox-Active Ligand Platform on Iron and Cobalt.Inorganic chemistry · 2019
Hydrazine Hydrate Accelerates Neocuproine-Copper Complex Generation and Utilization in Alkyne Reduction, a Significant Supplement Method for Catalytic Hydrogenation.The Journal of organic chemistry · 2021
Neocuproine ablates melanocytes in adult zebrafish.Zebrafish · 2008
Protein sulfhydration.Methods in enzymology · 2015
Anticandidal Cu(I) complexes with neocuproine and 1-(4-methoxyphenyl)piperazine based diphenylaminomethylphosphine: Is Cu-diimine moiety a pharmacophore?Journal of inorganic biochemistry · 2023

via PubMed

Wikidata facts

Mass: 208.1
Image: Neocuproine.jpg

Show 3 more facts

chemical formula: C₁₄H₁₂N₂
canonical SMILES: CC1=NC2=C(C=C1)C=CC3=C2N=C(C=C3)C
Commons category: Neocuproine

Sources (2)

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~3 min read

Article

5 sections

Contents

Synthesis and structure
Coordination chemistry
Other metals
References
Appendix: NMR Shifts

==Synthesis and structure== Neocuproine can be prepared by sequential Skraup reactions (Doebner-Miller reaction/condensation) of o-nitroaniline (2-Nitroaniline) with crotonaldehyde diacetate. An alternate synthesis involves the condensation of o-phenylenediamine, m-nitrobenzenesulphonate, and crotonaldehyde diacetate. This method gives higher yields but is less economical. Neocuproine crystallizes as a dihydrate and a hemihydrate. [[File:NIPHOJ.png|thumb|structure of [NiCl2(neocuproine)]2.|260px|left]]