Phenanthroline

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Structural formula
Structure of phenanthroline
General
Surname Phenanthroline
other names
  • 1,10-phenanthroline
  • 1,10-diazaphenanthrene
  • phen
Molecular formula C 12 H 8 N 2
Brief description

colorless, crystalline powder

External identifiers / databases
CAS number 66-71-7
EC number 200-629-2
ECHA InfoCard 100,000,572
PubChem 1318
ChemSpider 1278
DrugBank DB02365
Wikidata Q416005
properties
Molar mass 180.2 g mol −1
Physical state

firmly

Melting point
  • 93-94 ° C (hydrate)
  • 117 ° C (anhydrous)
solubility
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
06 - Toxic or very toxic 09 - Dangerous for the environment

danger

H and P phrases H: 301-410
P: 273-301 + 310-501
Toxicological data

132 mg kg −1 ( LD 50ratoral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Phenanthroline ( phen ) is formally a derivative of phenanthrene in which two methine groups (CH groups) have been exchanged for nitrogen atoms.

presentation

Phenanthroline can be prepared in accordance with Skraup's synthesis by heating 8-aminoquinoline or o - phenylenediamine with glycerol , nitrobenzene and concentrated sulfuric acid .

use

In complex chemistry it is used as a bidentate ligand with the abbreviation phen . The best-known phenanthroline complexes are ferroin and ferrocyphene , in which iron (II) and iron (III) ions are the central atoms. Ferroin is used as a redox indicator .

The heavy metal complexes of phenanthroline are suitable for quantitative analyzes due to their poor solubility, methyl- and phenyl-substituted derivatives such as bathocuproine and bathophenanthroline have an even higher selectivity .

Phenanthroline complexes are used as substrates for building supramolecular systems and for studying their properties, such as electron or photoelectron transfer .

In asymmetric homogeneously catalyzed reactions are chiral phenanthroline derivatives used as ligands.

Biological properties

The photosynthesis and carboxypeptidases are inhibited by 1,10-phenanthroline. The substance and its metal complexes intercalate into the DNA . Since the metal complexes function as metalloenzyme analogs, they are used as diagnostic tools in biochemical research.

See also

Individual evidence

  1. a b c d e f g h i j k Entry on 1,10-phenanthroline. In: Römpp Online . Georg Thieme Verlag, accessed on March 4, 2012.
  2. a b c Entry on 1,10-phenanthroline in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
  3. Entry on 1,10-phenanthroline in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .