Product Introduction
| 2,2'-Bipyridine Basic information |
| Product Name: | 2,2'-Bipyridine |
| Synonyms: | 2,6'-Bipyridine;bpy;2,2-Bispyridine;2,2'-Dipyridyl p.a.;2,2'-BIPYRIDINE (2,2'-Bipyridyl);2'-Bipyridine;2,2-Dipyridyl 99+%, White Crystalline Powder, Reagent Grade;α,α'-Dipyridyl, 2,2'-Dipyridyl |
| CAS: | 366-18-7 |
| MF: | C10H8N2 |
| MW: | 156.18 |
| EINECS: | 206-674-4 |
| Product Categories: | Aromatics;Analytical Chemistry;Pyridine;Pyridines derivates;Bipyridyls, etc. (Chelating Reagents);Chelating Reagents;Metalloprotease inhibitorProtease Inhibitors;Metalloproteinase InhibitorsEnzyme Inhibitors;Broad Spectrum Inhibitors of Proteolytic Enzyme Classes;Enzyme Inhibitors by Enzyme;L to;Protease Inhibitors;C9 to C46Derivatization Reagents TLC;TLC Reagents, D-FDerivatization Reagents TLC;Metal IonsTitration;TLC Reagents, A-CSpectroscopy;Derivatization Reagents TLC;Indicators;Redox IndicatorsDerivatization Reagents TLC;TLC Visualization Reagents (alphabetic sort);TLC Visualization Reagents (by application);UV/Vis Reagents;UV/Visible (UV/VIS) Spectroscopy;A-BAlphabetic;Alpha sort;Heterocyclic Building Blocks;Pyridines;Vitamins;Achiral Nitrogen;Py-N;B;BI - BZ;Pesticides&Metabolites;366-18-7 |
| Mol File: | 366-18-7.mol |
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| 2,2'-Bipyridine Chemical Properties |
| Melting point | 70-73 °C(lit.) |
| Boiling point | 273 °C(lit.) |
| density | 1.1668 (rough estimate) |
| vapor pressure | 0.584Pa at 25℃ |
| refractive index | 1.4820 (estimate) |
| Fp | 121 °C |
| storage temp. | room temp |
| solubility | 5.5g/l |
| pka | pK1:-0.52(+2);pK2:4.352(+1) (20°C) |
| form | Crystalline Powder |
| color | White to almost white |
| PH | 7.5 (5g/l, H2O, 25℃) |
| Odor | Characteristic odour |
| Water Solubility | 5.5 g/L 22 ºC |
| Merck | 14,3347 |
| BRN | 113089 |
| Stability: | Stable. Incompatible with strong oxidizing agents, most common metals. May be light sensitive. |
| InChIKey | ROFVEXUMMXZLPA-UHFFFAOYSA-N |
| CAS DataBase Reference | 366-18-7(CAS DataBase Reference) |
| NIST Chemistry Reference | 2,2'-Bipyridine(366-18-7) |
| EPA Substance Registry System | 2,2'-Bipyridine (366-18-7) |
| Safety Information |
| Hazard Codes | T,Xi |
| Risk Statements | 25-36/37/38-20/21-23/24/25-21 |
| Safety Statements | 36/37-45-36/37/39-26 |
| RIDADR | UN 2811 6.1/PG 3 |
| WGK Germany | 3 |
| RTECS | DW1750000 |
| F | 8 |
| Hazard Note | Irritant |
| TSCA | Yes |
| HazardClass | 6.1 |
| PackingGroup | III |
| HS Code | 29333999 |
| Hazardous Substances Data | 366-18-7(Hazardous Substances Data) |
| Toxicity | LD50 i.p. in mice: 200 mg/kg (Grady) |
| MSDS Information |
| Provider | Language |
|---|---|
| 2,2'-Bipyridine | English |
| SigmaAldrich | English |
| ACROS | English |
| ALFA | English |
| 2,2'-Bipyridine Usage And Synthesis |
| Chemical Properties | White to light red crystalline powder. Soluble in ethanol, ether, benzene, chloroform and petroleum ether, 1 part of this product is about 200 parts of water. |
| Uses | A high-affinity chelator of iron. A reagent used for the determination of iron. |
| Uses | 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. |
| Definition | ChEBI: 2,2'-bipyridine is a bipyridine in which the two pyridine moieties are linked by a bond between positions C-2 and C-2'. It has a role as a ferroptosis inhibitor and a chelator. |
| Preparation | 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. |
| Reactions | A large number of complexes of 2,2'-bipyridine have been described.It binds metals as a chelating ligand, forming a 5-membered chelate ring. |
| Synthesis Reference(s) | Journal of the American Chemical Society, 100, p. 5567, 1978 DOI: 10.1021/ja00485a053 Synthesis, p. 564, 1986 DOI: 10.1055/s-1986-31705 |
| General Description | 2,2′-Bipyridyl, is a symmetrical bipyridine commonly used as a neutral ligand for complexation with metal ions. The molecule is planar with trans-conformation and crystallizes in the monoclinic crystal system. |
| Biochem/physiol Actions | Metalloprotease inhibitor, high-affinity chelator of iron; may inhibit Fe2+ containing enzymes at 10?8?M. |
| Safety Profile | Poison by ingestion,subcutaneous, and intraperitoneal routes. Experimentalteratogenic data. Questionable carcinogen withexperimental tumorigenic data. Mutation data reported.When heated to decomposition it emits toxic fumes ofNOx. |
| Source | 2,2'-Bipyridine is a natural product found in Dichilus strictus, Dichilus gracilis, and other organisms with data available. |
| Purification Methods | 2,2'-Bipyridyl crystallises from hexane, or EtOH, or (after charcoal treatment of a CHCl3 solution) from pet ether. Also, it precipitates from a concentrated solution in EtOH by addition of H2O. Dry it in a vacuum over P2O5. It can be further purified by chromatography on Al2O3 or by sublimation. UV (EtOH): at 280nm (log 4.13). max [Airoldi et al. J Chem Soc, Dalton Trans 1913 1986, Beilstein 23 H 199, 23/8 V 16.] |
| 2,2'-Bipyridine Preparation Products And Raw materials |
| Raw materials | Ferric chloride-->2-Picoline-->5-METHYL-2,2'-BIPYRIDYL-->5,5'-DIMETHYL-2,2'-DIPYRIDYL-->2-Bromopyridine-->Neocuproine-->TRIETHYOXY-2-THIENYLSILANE 97 |
| Preparation Products | Tetrahydro-4H-pyran-4-one-->1,1'-Bis (di-t-butylphosphino)ferrocene palladium dichloride,-->1,1'-Bis(di-tert-butylphosphino)ferrocene-->3-(DIMETHYLCARBAMOYL)PHENYLBORONIC ACID-->4-(Dimethylamino)phenylboronic acid-->TRIS(2,2'-BIPYRIDYL)RUTHENIUM(II) CHLORIDE HEXAHYDRATE-->4,4'-DIBROMO-2,2'-BIPYRIDINE-->2,2'-BIPYRIDINE-4-CARBALDEHYDE-->(2,2'-BIPYRIDINE)DICHLOROPALLADIUM(II) |
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