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1,10-Phenanthroline

From Wikipedia, the free encyclopedia
Heterocyclic organic compound
Phenanthroline
1,10-phenanthroline
1,10-phenanthroline
Sample of 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 InfoCard100.000.572Edit this at Wikidata
EC Number
  • 200-629-2
  • monohydrate: 627-114-9
4040
KEGG
RTECS number
  • SF8300000
UNII
UN number2811
  • 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 mass180.21 g/mol
Appearancecolourless crystals
Density1.31 g/cm3
Melting point118.56 °C (245.41 °F; 391.71 K)[2]
Boiling point409.2[2]
high[2]
Solubility in other solventsacetone, 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 theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

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

Abbreviated "phen", or sometimes "o-phen" for ortho-phenanthroline, it is used as aligand incoordination chemistry, forming strongcomplexes with most metal ions.[3][4] It is often sold as themonohydrate.

Synthesis

[edit]

Phenanthroline can be prepared by two successiveSkraup reactions ofglycerol witho-phenylenediamine, catalyzed bysulfuric acid, and anoxidizing agent, traditionallyaqueousarsenic acid ornitrobenzene.[5] Dehydration ofglycerol givesacrolein which condenses with theamine followed by acyclization.

Reactions

[edit]

Oxidation of 1,10-phenanthroline with a mixture of nitric andsulfuric acids gives1,10-phenanthroline-5,6-dione.[6]

1,10-Phenanthroline forms manycoordination complexes. One example is the iron complex calledferroin.

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 bytitration with alcohols to a colourlessendpoint.[7]Grignard reagents may be similarly titrated.[8]

Pharmacology

[edit]

Phenanthroline is used inbiochemical andpharmacological research as aninhibitor of thedeubiquitinationenzymeRpn11.[9]

References

[edit]
  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. ^abcdeHaynes, 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.
  9. ^Song, Y.; Li, S.; Ray, A.; Das, D. S.; Qi, J.; Samur, M. K.; Tai, Y.-T.; Munshi, N.; Carrasco, R. D.; Chauhan, D.; Anderson, K. C. (2017-06-05)."Blockade of deubiquitylating enzyme Rpn11 triggers apoptosis in multiple myeloma cells and overcomes bortezomib resistance".Oncogene.36 (40):5631–5638.doi:10.1038/onc.2017.172.PMC 5705032.PMID 28581522.
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