Neocuproine

Base Information

• Chemical Name: Neocuproine
• CAS No.: 484-11-7
• Molecular Formula: C14H12N2
• Molecular Weight: 208.263
• Hs Code.: 29339990
• European Community (EC) Number: 207-601-9,230-732-8,628-478-1
• NSC Number: 4280
• UNII: 8E7D2SH3BV
• DSSTox Substance ID: DTXSID5060065
• Nikkaji Number: J5.993E
• Wikipedia: Neocuproine
• Wikidata: Q409347
• ChEMBL ID: CHEMBL375781
• Mol file: 484-11-7.mol

Synonyms:2,9-dimethyl-1,10-phenanthroline;2,9-dimethyl-o-phenanthroline;3,6-dimethyl-4,5-phenanthroline;neocuproine;neocuproine hydrochloride;neocuproine monohydrochloride

Chemical Property of Neocuproine

Chemical Property:

• Appearance/Colour: off-white to very pale yellow crystalline powder
• Vapor Pressure: 2.89E-05mmHg at 25°C
• Melting Point: 159-164 °C
• Refractive Index: 1.693
• Boiling Point: 367.4 °C at 760 mmHg
• PKA: 6.01±0.30(Predicted)
• Flash Point: 159.7 °C
• PSA: 25.78000
• Density: 1.178 g/cm³
• LogP: 3.39980
• Storage Temp.: Store at +15°C to +25°C.
• Sensitive.: Light Sensitive
• Solubility.: methanol: 0.1 g/mL, clear
• Water Solubility.: slightly soluble
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 208.100048391
• Heavy Atom Count: 16
• Complexity: 227

Purity/Quality:

99.9% ^*data from raw suppliers

Neocuproine 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22-22
• Safety Statements: 26-36/37/39-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Polycyclic Aromatic Hydrocarbons
• Canonical SMILES: CC1=NC2=C(C=C1)C=CC3=C2N=C(C=C3)C
• Uses: Due to the steric hindrance of the methyl groups attached to the carbon atoms adjacent to the nitrogen donor atoms of phenanthroline, the reagent does not give the low spin vivid red complex characteristic of phenanthroline derivatives with iron(II). However, in the presence of reducing agents it reacts with copper to give a copper(I) complex of composition MA2 and of tetrahedral symmetry. This chelate is insoluble in water and can be extracted by chloroform in which the absorption maximum of the complex appears at 457 nm. In this way the concentration of the complex can be measured. The method is suitable for the determination of copper in iron, manganese and vanadium ores even in the presence of aluminium, germanium, titanium and silicon. Neocuproine is today considered one of the most selective reagents. Unfortunately, it is rather expensive. 2,3-bis-(2-pyridyl)quinoxaline, prepared by Belcher et al. by condensation of o-diketone, 2,2'-dipyridyl and 0-phenylenediamine(44) contains the functional grouping characteristic of cuproine; it is quite suitable for the determination of copper and it is cheap. Starting with various substituted o-phenylene-diamines Belcher synthesized 25 different quinoxaline derivatives, of which 2,3-bis-[2-(-methyl)-pyridyl)]quinoxaline proved to be identical with neocuproine as regards analytical selectivity. Besides copper, titanium(III) is the only metal ion which gives a colour reaction with the reagent. However, the coloured titanium(III) complex is formed only at lower pH and hence it does not interfere with the determination of copper. The copper complex of the reagent can be extracted quantitatively with isopentyl alcohol usually as a perchlorate ion pair. Neocuproine is a phenanthroline based metal ion chelating agent.

Technology Process of Neocuproine

There total 16 articles about Neocuproine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

2,3-diaminobenzene-1,4-dicarbaldehyde + acetone (67-64-1) → 2.9-dimethyl-1,10-phenanthroline (484-11-7)

Guidance literature:

With potassium hydroxide; In ethanol; at 80 ℃; for 8h; Schlenk technique;

DOI:10.1002/cjoc.201800496

Reference yield: 64.0%

2,3-dinitrobenzene-1,4-dicarbaldehyde + acetone (67-64-1) → 2.9-dimethyl-1,10-phenanthroline (484-11-7)

Guidance literature:

With potassium hydroxide; In ethanol; for 8h; Sealed tube; Reflux;

Reference yield: 59.0%

C14H12Br2N2 (942267-04-1) → 2.9-dimethyl-1,10-phenanthroline (484-11-7)

Guidance literature:

With copper; In 1-methyl-pyrrolidin-2-one; for 30h; Heating;

DOI:10.1016/j.tetlet.2007.03.073

upstream raw materials:

2-methyl-8-aminoquinoline

1,1-diacetoxy-but-2-ene

1,10-Phenanthroline

methyllithium

Downstream raw materials:

1,10-phenanthroline-2,9-dicarboxaldehyde

2,9-diphenylethyl-1,10-phenanthroline

2,9-bis-{2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-ethyl}-[1,10]phenanthroline

PhenDC3

Refernces

Synthesis and characterization of lead(II) complexes with the 4-methoxybenzoyltrifluoroacetonate ligand

10.1515/znb-2009-0906

The research investigates the intermolecular interactions of ligands in lead(II) complexes, focusing on the stereochemical activity of the lone electron pair and noncovalent donor-acceptor interactions that form multidimensional networks. The compounds [Pb2(phen)2(mbtfa)4] (1) and [Pb2(dmp)2(mbtfa)4] (2) were synthesized using 1,10-phenanthroline (phen), 2,9-dimethyl-1,10-phenanthroline (dmp), and 4-methoxybenzoyl trifluoroacetonate (mbtfa) as ligands, and characterized by elemental analysis and crystallography. The study found that the coordination numbers of Pb(II) were seven and eight for compounds 1 and 2, respectively, and that the complexes exhibited weak directional intermolecular interactions such as C–H···F, O···H–C, and π-π stacking. The research concluded that the stereochemical activity of the Pb(II) lone pair and the stability of the complexes were influenced by the nature of the ligands and their interactions, with compound 1 showing stronger intermolecular interactions and higher thermal stability than compound 2.