1,10-Phenanthroline

Heterocyclic organic compound changed changed 464199880 Phenanthroline correct ?? 1,10-phenanthroline.svg 1,10-phenanthroline Sample of 1,10-Phenanthroline.jpg Sample of 1,10-Phenanthroline 1,10-Phenanthroline Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) The Royal Society of Chemistry 2014 Cambridge 211 10.1039/9781849733069-FP001 978-0-85404-182-4 monohydrate correct chemspider 1278 19955 1/C12H8N2/c1-3-9-5-6-10-4-2-8-14-12(10)11(9)13-7-1/h1-8H DGEZNRSVGBDHLK-UHFFFAOYAW correct EBI 415879 1318 21226 200-629-2 627-114-9 1255788 C00604 126461 4040 correct chemspider 1S/C12H8N2/c1-3-9-5-6-10-4-2-8-14-12(10)11(9)13-7-1/h1-8H correct chemspider DGEZNRSVGBDHLK-UHFFFAOYSA-N 66-71-7 correct CAS 5144-89-8 correct CAS (monohydrate) 2811 correct FDA W4X6ZO7939 correct FDA KSX215X00E correct drugbank DB02365 correct EBI 44975 c1cc2ccc3cccnc3c2nc1 C1=CC2=C(C3=C(C=CC=N3)C=C2)N=C1.O SF8300000 C12H8N2 180.21 g/mol colourless crystals 1.31 g/cm3 high other solvents acetone, ethanol 118.56 Haynes, William M. 2016 CRC Handbook of Chemistry and Physics 97th CRC Press 978-1-4987-5429-3 3.444 409.2°C 4.84 (phenH+) mild neurotoxin, strong nephrotoxin, and powerful diuretic 06 09 Danger 301 410 264 270 273 301+310 321 330 391 405 501 2,2'-bipyridineferroinphenanthrene 1,10-Phenanthroline (phen) is a heterocyclic organic 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 called phenanthrene. Abbreviated "phen", or sometimes "o-phen" for ortho-phenanthroline, it is used as a ligand in coordination chemistry, forming strong complexes with most metal ions.Luman, C.R. and Castellano, F.N. (2003) "Phenanthroline Ligands" in Comprehensive Coordination Chemistry II. Elsevier. 978-0-08-043748-4.10.1039/cs9942300327 1,10-Phenanthroline: A versatile ligand 1994 Sammes Peter G. Yahioglu Gokhan Chemical Society Reviews 23 5 327 It is often sold as the monohydrate. Synthesis Phenanthroline can 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. J. Chem. Soc. 155–157 1946 10.1039/jr9460000155 20983293 43. Attempts to find new antimalarials. Part XXIV. Derivatives of o-phenanthroline (7 : 8 : 3 : 2-pyridoquinoline) Halcrow Barbara E. Kermack William O. 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.10.1071/ch9701023 Derivatives of 1,10-Phenanthroline-5,6-quinone 1970 Dickeson JE Summers LA Australian Journal of Chemistry 23 5 1023 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. Fagan, Paul J. Nugent, William A. 1-Phenyl-2,3,4,5-Tetramethylphosphole 9 653 1998 CV9P0653 Grignard reagents may be similarly titrated. A Convenient Method for Determining the Concentration of Grignard Reagents Lin, Ho-Shen Paquette, Leo A. Synth. Commun. 24 2503–2506 1994 10.1080/00397919408010560 17 Pharmacology Phenanthroline is used in biochemical and pharmacological research as an inhibitor of the deubiquitination enzyme Rpn11.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. Blockade of deubiquitylating enzyme Rpn11 triggers apoptosis in multiple myeloma cells and overcomes bortezomib resistance Oncogene 36 40 2017-06-05 5631–5638 28581522 5705032 10.1038/onc.2017.172 free References 30em Category:Redox indicators Category:Chelating agents