1,10-Phenanthroline

Abstract

[66-71-7] C12H8N2 (MW 180.21) InChI = 1S/C12H8N2/c1-3-9-5-6-10-4-2-8-14-12(10)11(9)13-7-1/h1-8H InChIKey = DGEZNRSVGBDHLK-UHFFFAOYSA-N (reagent used as supporting ligand in a wide variety of metal-catalyzed processes) Alternate Name: Phen. Physical Data: mp 100–104 °C. Solubility: soluble in alcohol, acetone, ether, and benzene; slightly soluble in water. Form Supplied in: white crystalline solid; widely available. Preparative Methods: classical approaches toward Phen imply both Skraup and Friedlander reactions. The former synthesis consists of two successive condensations of glycerol with 1,2-diaminobenzene catalyzed by sulfuric acid in the presence of an oxidizing agent, traditionally aqueous arsenic acid or nitrobenzene.1 Alternatively, Friedlander reaction involves the condensation of 8-aminoquinolinecarbaldehyde with Acetaldehyde in the presence of Potassium Hydroxide at reflux in ethanol.2 Other approaches include the photochemical electrocyclic reactions of 3-alkenyl-2,2′-bipyridines,3 condensation of Meldrum's acid, trimethyl orthoacetate, and 1,2-diamine followed by thermal cyclization–decarboxylation,4 and Ullmann intramolecular coupling of cis-1,2-di(2-bromo-3-pyridyl)alkenes,5 among others. Handling, Storage, and Precautions: store in a cool, dry, well-ventilated, locked storeroom. Phen is a highly irritating agent and hence must be used only in a well-ventilated fume hood avoiding eye contact. Toxic if swallowed; very toxic to aquatic organisms and may cause long-term adverse effects in the aquatic environment. Toxicity, LD50 (oral, rat) = 130 mg kg−1. Incompatible with strong oxidizers.