2,2'-Bipyridil
bpy · BIPY · Bipyridine · 2,2-BIPYRIDINE · 2,2-BIPYRIDYL · 2-(2-Pyridyl)pyridine · 2,2'-Bipyridyl · 2,2-Bispyridine
Identifikatoren & physikalische Daten
| CAS No. | 366-18-7 |
|---|---|
| Summenformel | C10H8N2 |
| Durchschnittliche Molmasse | 156,18 g/mol |
| Monoisotopische Masse | 156,06874826 g/mol |
| SMILES | c1ccc(-c2ccccn2)nc1 |
| InChIKey | ROFVEXUMMXZLPA-UHFFFAOYSA-N |
| PubChem CID | 1474 |
| ChEMBL | CHEMBL39879 |
| ChEBI | CHEBI:30351 |
| EC No. | 206-674-4 |
| DTXSID | DTXSID9040635 |
| Lokaler Name | 2,2'-Bipyridil |
Chemische & physikalische Eigenschaften
| XLogP | 1,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 25,8 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 12 |
| Formalladung | 0 |
| Komplexität | 120 |
| Stoffklassen | Nitrogen Compounds -> Pyridines |
| SpringerMaterials Properties | 15N nuclear magnetic resonance spectrum |
| LogP (Verteilungskoeffizient) | log Kow= 1.50 |
| Color/Form | White crystalsCrystals from dilute alcoholPRISMS FROM PETROLEUM ETHER |
| Löslichkeit | Very sol in alcohol, ether, and benzeneSoluble in oxygenated solventsIn water, 5.93X10+3 mg/l @ 25 °CSolubility in water, g/100ml: 6.45.5g/l5.5 g/L 22 ºC |
| Flammpunkt | 121 °C |
| Siedepunkt | 273.5 °C272-273 °C273 °C(lit.) |
| Decomposition | When heated to decomposition it emits toxic fumes of /nitrogen oxides/. |
| Schmelzpunkt | 72 °C70 °C70-73 °C(lit.) |
| Dampfdruck | 0.000013 [mmHg]0.584Pa at 25℃ |
| Physical Description | White solid[Hawley] White or yellow crystalline solid[MSDSonline]WHITE CRYSTALS. |
| Ionization Efficiency | Positive3.842.7Agilent XCTElectrospray ionizationformic acid (5.3nM) |
| Dichte | 1.1668 (rough estimate) |
| Brechungsindex | 1.4820 (estimate) |
| Lagerbedingungen | room temp |
| pKa (Säurekonstante) | pK1:-0.52(+2)pK2:4.352(+1) (20°C) |
| Aggregatzustand | Crystalline Powder |
| Farbe | White to almost white |
| pH | 7.5 (5g/l, H2O, 25℃) |
| Geruch | Characteristic odour |
| Biologische Quelle | synthetic (organic) |
| Merck | 14,3347 |
| BRN | 113089 |
| Henry-Konstante | 1.8×104 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | Stable. Incompatible with strong oxidizing agents, most common metals. May be light sensitive. |
| InChI | 1S/C10H8N2/c1-3-7-11-9(5-1)10-6-2-4-8-12-10/h1-8H |
| InChIKey | ROFVEXUMMXZLPA-UHFFFAOYSA-N |
| SMILES | c1ccc(nc1)-c2ccccn2 |
| CAS Datenbank | 366-18-7(CAS DataBase Reference) |
| NIST chemische Informationen | 2,2'-Bipyridine(366-18-7) |
| EPA chemische Informationen | 2,2'-Bipyridine (366-18-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 1.5% (10 of 659) of reports.DangerH301+H311 (34.9%): Toxic if swallowed or in contact with skin [Danger Acute toxicity, oralacute toxicity, dermal]P262, P264, P264+P265, P270, P273, P280, P301+P316, P302+P352, P305+P351+P338, P316, P317, P321, P330, P337+P317, P361+P364, P362+P364, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 659 reports by companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: 2,2'-Bipyridine2,2'-Bipyridine is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2,2'-Bipyridine 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)Status: Active Update: 30-09-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/122702,2'-Bipyridine: Does not have an individual approval but may be used under an appropriate group standard |
| Brandgefahren | Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air. |
| Gefahrenübersicht | A skin, eye, and mucous membrane irritantEmergency treatment: PyridinePyridine is an irritant that causes CNS depression after ingestion of 1/2 cup or inhalation of 6-12 ppmIt can cause liver and kidney injury[HSDB] A skin, eye, and respiratory tract irritant[ICSC] A teratogen (limb malformations) in rat studies[REPROTOX] An irritant[MSDSonline] See 4,4'-Bipyridine and 2,3'-Bipyridine. |
| Chemical Dangers | On combustion, forms toxic gases including nitrogen oxides. Reacts with oxidants. |
| Physical Dangers | Dust explosion possible if in powder or granular form, mixed with air. |
| Hazard Classes and Categories | Acute Tox. 3 (94.5%) |
Anwendungen & Verwendung
Verwenden
2,2'-bipyridine acts as a bidentate chelating ligand which form complexes with transition metal ions and shows antifungal, antibacterial and antiviral activity. It is used for the colorimetric determination of iron as well as oxidation reduction indicators to confirm the presence of ferrous ion in soils. It forms complexes with ruthenium and platinum, exhibit intense luminescence, which may have practical applications. Copper(I) bipyridine complexes involved in the oxidation of alcohols under aerobic conditions.
Herstellung & Synthese
synthetische
2,2'-bipyridine is synthesized by the reaction of pyridine with ferric chloride. Take 70g of anhydrous pyridine and mix with 13g of anhydrous ferric chloride, heat and react at 300℃ in a sealed tube for about 35h. After cooling, the reactant solidified into red-black crystals, the sealing tube was opened, and the red-black solution of the solid was washed out with a small amount of hot water. The oily impurities were removed by extraction with ether. After neutralization with sodium bicarbonate, excess pyridine was removed by heating with steam. The mixture was then made strongly basic, and the 2,2'-bipyridine was distilled off with steam.