1,10-Phenanthrolin
1,10-PHENANTHROLINE · phen · 1,10-Phen · 10-Phenanthroline · 1,10-Fenanthrolin · 1,10-o-Phenanthroline · 1,10-Phenanthroline anhydrate · 4,5-Phenanthroline
Identifikatoren & physikalische Daten
| CAS No. | 66-71-7 |
|---|---|
| Summenformel | C12H8N2 |
| Durchschnittliche Molmasse | 180,2 g/mol |
| Monoisotopische Masse | 180,06874826 g/mol |
| SMILES | c1cnc2c(c1)ccc1cccnc12 |
| InChIKey | DGEZNRSVGBDHLK-UHFFFAOYSA-N |
| PubChem CID | 1318 |
| ChEMBL | CHEMBL415879 |
| ChEBI | CHEBI:44975 |
| EC No. | 200-629-2 |
| DTXSID | DTXSID1025857 |
| Lokaler Name | 1,10-Phenanthrolin |
Chemische & physikalische Eigenschaften
| XLogP | 1,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 25,8 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 14 |
| Formalladung | 0 |
| Komplexität | 182 |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| Polymers | Other Classes -> Polycyclic Aromatic Hydrocarbons |
| SpringerMaterials Properties | Angular frequency |
| LogP (Verteilungskoeffizient) | 1.93 |
| Löslichkeit | >27 [ug/mL] (The mean of the results at pH 7.4)2.69g/lslightly soluble |
| Siedepunkt | > 300 °C>330°C |
| Schmelzpunkt | 117 °C114-117 °C(lit.) |
| Dampfdruck | 0.0000523 [mmHg] |
| Physical Description | LiquidWhite solid[Merck Index] Hygroscopic solid[Sigma-Aldrich MSDS] |
| Ionization Efficiency | Positive3.252.7Agilent XCTElectrospray ionizationformic acid (5.3nM) |
| Dissociation Constants | 4.27 (at 20 °C) |
| Collision Cross Section | 132.4 Ų [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: TOXCASTSource Identifier: DTXSID1025857] |
| Dichte | 1.1836 (rough estimate) |
| Brechungsindex | 1.5200 (estimate) |
| Flammpunkt | >330°C |
| Lagerbedingungen | Store below +30°C. |
| pKa (Säurekonstante) | 4.84(at 25℃) |
| Aggregatzustand | Powder |
| Farbe | White to light yellow or light pink |
| Merck | 14,7214 |
| BRN | 126461 |
| Henry-Konstante | 1.1×105 mol/(m3Pa) at 25℃, Zhang et al. (2010) |
| Stabilität | Stable. Hygroscopic. Store under nitrogen. Incompatible with strong acids, strong oxidizing agents. |
| 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 |
| SMILES | c1cnc2c(c1)ccc3cccnc23 |
| CAS Datenbank | 66-71-7(CAS DataBase Reference) |
| NIST chemische Informationen | o-Phenanthroline(66-71-7) |
| EPA chemische Informationen | 1,10-Phenanthroline (66-71-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301: Toxic if swallowed [Danger Acute toxicity, oral]P264, P270, P273, P301+P316, P321, P330, P391, P405, and P501 (click each P-code to see the statement)H301 (99.8%): Toxic if swallowed [Danger Acute toxicity, oral] |
|---|---|
| Regulatorische Informationen | Chemical: 1,10-Phenanthroline1,10-Phenanthroline is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,10-Phenanthroline are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)1,10-Phenanthroline: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | Causes kidney changes in intraperitoneal lethal-dose studies of mice (LD50 = 75 mg/kg)[RTECS] May cause irritationToxic by ingestion[Sigma-Aldrich MSDS] See 2,2'-Bipyridine. See POLYCYCLIC AROMATIC HYDROCARBONS. |
| Hazard Classes and Categories | Acute Tox. 3 (99.8%)Acute toxicity - category 3Acute Tox. 3 * |
| Protective Action Criteria (PAC) | 0.25 [mg/m3]2.7 [mg/m3]16 [mg/m3] |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2811 6.1/PG 3 |
| Zollcode | 29339990 |
| RTECS-Nr. | SF8437000 |
| R-Sätze (R) | 25-50/53 |
| Toxizität | dni-hmn:leu 5 mg/L ONCOBS 46,193,89 |
| Gefahrensymbole |
Anwendungen & Verwendung
Beschreibung
o-Phenanthroline is a white crystalline powder and serves as an organic intermediate. It has multiple uses, acting as both a redox indicator and a reagent for the determination of various metals such as ferrous, palladium, vanadium, copper, and iron.
Verwenden
o-Phenanthroline is a commonly used redox indicator and also a bidentate ligand. It has been widely used in transition metal-catalyzed cross-coupling reactions and CH bond activation reactions. It also acts as a chelating agent, forming complexes with most metal ions. In addition, it functions as a ligand employed in the spectrophotometric determination of metals and photocatalytic reduction of carbon dioxide.
Herstellung & Synthese
synthetische
1,10-Phenanthroline is prepared by heating o-phenylenediamine, glycerin, nitrobenzene and concentrated sulfuric acid.