1,10-Phenanthroline

Phenanthroline
Names
	Preferred IUPAC name 1,10-Phenanthroline
Identifiers
CAS Number	66-71-7 ; monohydrate: 5144-89-8 (monohydrate) ;
3D model (JSmol)	Interactive image; monohydrate: Interactive image;
Beilstein Reference	126461
ChEBI	CHEBI:44975 ;
ChEMBL	ChEMBL415879 ; monohydrate: ChEMBL1255788;
ChemSpider	1278 ; monohydrate: 19955;
DrugBank	DB02365 ;
ECHA InfoCard	100.000.572
EC Number	200-629-2; monohydrate: 627-114-9;
Gmelin Reference	4040
KEGG	C00604;
PubChem CID	1318; monohydrate: 21226;
RTECS number	SF8300000;
UNII	W4X6ZO7939 ; monohydrate: KSX215X00E ;
UN number	2811
CompTox Dashboard (EPA)	DTXSID1025857 ;
	InChI InChI=1S/C12H8N2/c1-3-9-5-6-10-4-2-8-14-12(10)11(9)13-7-1/h1-8H Key: DGEZNRSVGBDHLK-UHFFFAOYSA-N ; InChI=1/C12H8N2/c1-3-9-5-6-10-4-2-8-14-12(10)11(9)13-7-1/h1-8H Key: DGEZNRSVGBDHLK-UHFFFAOYAW;
	SMILES c1cc2ccc3cccnc3c2nc1; monohydrate: C1=CC2=C(C3=C(C=CC=N3)C=C2)N=C1.O;
Properties
Chemical formula	C12H8N2
Molar mass	180.21 g/mol
Appearance	colourless crystals
Density	1.31 g/cm3
Melting point	118.56 °C (245.41 °F; 391.71 K)
Boiling point	409.2
Solubility in water	high
Solubility in other solvents	acetone, ethanol
Acidity (pKa)	4.84 (phenH+)
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	mild neurotoxin, strong nephrotoxin, and powerful diuretic
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H410
Precautionary statements	P264, P270, P273, P301+P310, P321, P330, P391, P405, P501
Related compounds
Related compounds	2,2'-bipyridine; ferroin; phenanthrene
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

1,10-Phenanthroline (phen) is a heterocyclic organic compound. It is a white solid that is soluble in organic solvents. The 1,10 refer to the location of the nitrogen atoms that replace CH's in the hydrocarbon called phenanthrene.

Abbreviated "phen", it is used as a ligand in coordination chemistry, forming strong complexes with most metal ions.^[3]^[4] It is often sold as the monohydrate.

^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 211. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
^ ^a ^b ^c ^d ^e Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 3.444. ISBN 978-1-4987-5429-3.
^ Luman, C.R. and Castellano, F.N. (2003) "Phenanthroline Ligands" in Comprehensive Coordination Chemistry II. Elsevier. ISBN 978-0-08-043748-4.
^ Sammes, Peter G.; Yahioglu, Gokhan (1994). "1,10-Phenanthroline: A versatile ligand". Chemical Society Reviews. 23 (5): 327. doi:10.1039/cs9942300327.

[iupac2013-1] Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 211. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.

[crc-2] Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 3.444. ISBN 978-1-4987-5429-3.

[Castellano-3] Luman, C.R. and Castellano, F.N. (2003) "Phenanthroline Ligands" in Comprehensive Coordination Chemistry II. Elsevier. ISBN 978-0-08-043748-4.

[4] Sammes, Peter G.; Yahioglu, Gokhan (1994). "1,10-Phenanthroline: A versatile ligand". Chemical Society Reviews. 23 (5): 327. doi:10.1039/cs9942300327.

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