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Neocuproine

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Neocuproine Basic information

Product Name:
Neocuproine
Synonyms:
  • TIMTEC-BB SBB008718
  • NEOCUPROINE REAG
  • NEOCUPROINE
  • 10-Phenanthroline,2,9-dimethyl-1
  • 2,9-dimethyl-10-phenanthroline
  • 2,9-Dimethyl-o-phenanthroline
  • 2,9-Dimethylphenanthroline
  • 2,9 DiMethy 1,10-phenanthrofine
CAS:
484-11-7
MF:
C14H12N2
MW:
208.26
EINECS:
207-601-9
Product Categories:
  • Analytical Chemistry
  • Chelating Reagents
  • Phenanthrolines
  • MOFS COFS
Mol File:
484-11-7.mol
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Neocuproine Chemical Properties

Melting point:
159-164 °C
Boiling point:
337.46°C (rough estimate)
Density 
1.1345 (rough estimate)
refractive index 
1.6152 (estimate)
RTECS 
SF8380000
storage temp. 
Keep in dark place,Sealed in dry,Room Temperature
solubility 
methanol: 0.1 g/mL, clear
pka
6.01±0.30(Predicted)
form 
crystalline
color 
white to beige
Water Solubility 
slightly soluble
Sensitive 
Light Sensitive
Merck 
6449
InChIKey
IYRGXJIJGHOCFS-UHFFFAOYSA-N
CAS DataBase Reference
484-11-7(CAS DataBase Reference)
NIST Chemistry Reference
1,10-Phenanthroline, 2,9-dimethyl-(484-11-7)
EPA Substance Registry System
1,10-Phenanthroline, 2,9-dimethyl- (484-11-7)
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Safety Information

Hazard Codes 
Xi,Xn
Risk Statements 
36/37/38-20/21/22-22
Safety Statements 
26-36/37/39-36-24/25
WGK Germany 
3
TSCA 
Yes
HS Code 
29339990

MSDS

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Neocuproine Usage And Synthesis

Chemical Properties

OFF-WHITE TO VERY PALE YELLOW CRYSTALLINE POWDER

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.

Definition

ChEBI: A member of the class of phenanthrolines that is 1,10-phenanthroline bearing two methyl substituents at positions 2 and 9.

Purification Methods

Purifiy it as the hemihydrate by crystallisation from water and as the anhydrous base from *benzene. [Beilstein 23/8 V 527.]

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