| Identification | More | [Name]
2,2'-Dipyridyl | [CAS]
366-18-7 | [Synonyms]
2,2'-BIPYRIDINE
2,2-BIPYRIDINE
2,2'-BIPYRIDYL
2,2-BIPYRIDYL
2,2'-DIPYRIDYL
2-PYRIDIN-2-YLPYRIDINE
A,A'-DIPYRIDYL
ALPHA, ALPHA'-BIPYRIDINE
ALPHA, ALPHA'-BIPYRIDYL
ALPHA,ALPHA'-DIPYRIDYL
BIPY
BIPYRIDINE(2,2'-)
CI-588
'LGC' (1607)
,’-Dipyridyl
2-(2-Pyridyl)pyridine
2,2’-bipyridin
2,2’-dipyridine
2,2'-Bipyridin
2,2'-Dipyridine | [EINECS(EC#)]
206-674-4 | [Molecular Formula]
C10H8N2 | [MDL Number]
MFCD00006212 | [Molecular Weight]
156.18 | [MOL File]
366-18-7.mol |
| Chemical Properties | Back Directory | [Appearance]
White crystalline powder | [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. ]
Store at RT. | [solubility ]
5.5g/l | [form ]
Crystalline Powder | [pka]
pK1:-0.52(+2);pK2:4.352(+1) (20°C) | [color ]
White to almost white | [Odor]
Characteristic odour | [PH]
7.5 (5g/l, H2O, 25℃) | [Stability:]
Stable. Incompatible with strong oxidizing agents, most common metals. May be light sensitive. | [Water Solubility ]
5.5 g/L 22 ºC | [Detection Methods]
GC,HPLC | [Merck ]
14,3347 | [BRN ]
113089 | [InChIKey]
ROFVEXUMMXZLPA-UHFFFAOYSA-N | [CAS DataBase Reference]
366-18-7(CAS DataBase Reference) | [NIST Chemistry Reference]
| [EPA Substance Registry System]
366-18-7(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T,Xi | [Risk Statements ]
R25:Toxic if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21:Harmful by inhalation and in contact with skin .
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S36/37:Wear suitable protective clothing and gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [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) |
| Raw materials And Preparation Products | Back Directory | [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) |
| Hazard Information | Back Directory | [Chemical Properties]
White crystalline powder | [Uses]
A high-affinity chelator of iron | [Uses]
As a reagent for the determination of iron. | [Definition]
ChEBI: A bipyridine in which the two pyridine moieties are linked by a bond between positions C-2 and C-2'. | [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.] |
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