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1,10-Phenanthroline

Phenanthroline
1,10-phenanthroline
Sample of 1,10-Phenanthroline
Names
Preferred IUPAC name
1,10-Phenanthroline[1]
Identifiers
3D model (JSmol)
126461
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.572 Edit this at Wikidata
EC Number
  • 200-629-2
  • monohydrate: 627-114-9
4040
KEGG
RTECS number
  • SF8300000
UNII
UN number 2811
  • InChI=1S/C12H8N2/c1-3-9-5-6-10-4-2-8-14-12(10)11(9)13-7-1/h1-8H checkY
    Key: DGEZNRSVGBDHLK-UHFFFAOYSA-N checkY
  • 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
  • c1cc2ccc3cccnc3c2nc1
  • monohydrate: C1=CC2=C(C3=C(C=CC=N3)C=C2)N=C1.O
Properties
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)[2]
Boiling point 409.2[2]
high[2]
Solubility in other solvents acetone, ethanol[2]
Acidity (pKa) 4.84 (phenH+)[2]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 mild neurotoxin, strong nephrotoxin, and powerful diuretic
GHS labelling:
GHS06: ToxicGHS09: Environmental hazard
Danger
H301, H410
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).
checkY verify (what is checkY☒N ?)

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.

Synthesis

Phenanthroline may be prepared by two successive Skraup reactions of glycerol with o-phenylenediamine, catalyzed by sulfuric acid, and an oxidizing agent, traditionally aqueous arsenic acid or nitrobenzene.[5] Dehydration of glycerol gives acrolein which condenses with the amine followed by a cyclization.

Reactions

Oxidation of 1,10-phenanthroline with a mixture of nitric and sulfuric acids gives 1,10-phenanthroline-5,6-dione.[6]

1,10-Phenanthroline forms many coordination complexes. One example is the iron complex called ferroin.

Alkyllithium reagents form deeply colored derivatives with phenanthroline. The alkyllithium content of solutions can be determined by treatment of such reagents with small amounts of phenanthroline (ca. 1 mg) followed by titration with alcohols to a colourless endpoint.[7] Grignard reagents may be similarly titrated.[8]

References

  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.
  2. ^ 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.
  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.
  5. ^ Halcrow, Barbara E.; Kermack, William O. (1946). "43. Attempts to find new antimalarials. Part XXIV. Derivatives of o-phenanthroline (7 : 8 : 3′ : 2′-pyridoquinoline)". J. Chem. Soc.: 155–157. doi:10.1039/jr9460000155. PMID 20983293.
  6. ^ Dickeson, JE; Summers, LA (1970). "Derivatives of 1,10-Phenanthroline-5,6-quinone". Australian Journal of Chemistry. 23 (5): 1023. doi:10.1071/ch9701023.
  7. ^ Fagan, Paul J.; Nugent, William A. (1998). "1-Phenyl-2,3,4,5-Tetramethylphosphole". Organic Syntheses; Collected Volumes, vol. 9, p. 653.
  8. ^ Lin, Ho-Shen; Paquette, Leo A. (1994). "A Convenient Method for Determining the Concentration of Grignard Reagents". Synth. Commun. 24 (17): 2503–2506. doi:10.1080/00397919408010560.
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