Structure via PubChem · Public domain (PubChem)
neocuproine
Sign in to saveAlso 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.
Chemical data
- Formula
- C14H12N2
- Molecular weight
- 208.26 g/mol
- IUPAC name
- 2,9-dimethyl-1,10-phenanthroline
- SMILES
- CC1=NC2=C(C=C1)C=CC3=C2N=C(C=C3)C
- InChIKey
- IYRGXJIJGHOCFS-UHFFFAOYSA-N
- XLogP
- 3.3
- Polar surface area
- 25.8 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
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
- Subclass of
- chemical compound
- 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)
via Wikidata · CC0
~3 min read
Encyclopedic overview
5 sectionsContents
- Synthesis and structure
- Coordination chemistry
- Other metals
- References
- Appendix: NMR Shifts
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.
==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]]
Excerpted from Wikipedia’s “neocuproine” article, available under the CC BY-SA 4.0 licence.
Gallery (2)
Available in 10 languages
via Wikidata sitelinks · CC0