Phenanthroline

Structural formula
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	heavy in water (2.69 g l −1 at 25 ° C) soluble in ethanol and acetone
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 301-410 P: 273-301 + 310-501
Toxicological data	132 mg kg −1 ( LD 50 ,  rat ,  oral )
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

• List of ligand abbreviations

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 .