| Identification | More | [Name]
4,4'-Bipyridine | [CAS]
553-26-4 | [Synonyms]
4,4,4'-DIPYRIDYL
4,4'-BIPYRIDINE
4,4-BIPYRIDINE
4,4'-BIPYRIDYL
4,4'-BIPYRIDYL HYDRATE
4, 4'-DIPYRIDINE
4,4'-DIPYRIDYL
4,4-DIPYRIDYL
4-PYRIDIN-4-YLPYRIDINE
GAMMA,GAMMA'-DIPYRIDYL
GAMMA,GAMMA-DIPYRIDYL
'LGC' (1608)
4-(4-Pyridyl)pyridine
4,4’-Bipyridine,dihydrate
Bipyridine, 4,4'-
gamma,gamma’-bipyridyl
gamma,gamma'-Bipyridyl
4,4'Bipyridinyl
4,4'-BIPYRIDINE ANHYDROUS PESTANAL
4,4'-Bipyridyl,98% | [EINECS(EC#)]
209-036-3 | [Molecular Formula]
C10H8N2 | [MDL Number]
MFCD00006416 | [Molecular Weight]
156.18 | [MOL File]
553-26-4.mol |
| Chemical Properties | Back Directory | [Appearance]
off-white to tan powder | [Melting point ]
109-112 °C(lit.)
| [Boiling point ]
305 °C(lit.)
| [density ]
1.2814 (rough estimate) | [refractive index ]
1.6057 (estimate) | [Fp ]
304-305°C | [storage temp. ]
Store below +30°C. | [solubility ]
4.5g/l | [form ]
Powder | [pka]
pK1:3.17(+2);pK2:4.82(+1) (25°C) | [color ]
Off-white to beige | [Stability:]
Stable. Incompatible with strong oxidizing agents, strong acids. | [Water Solubility ]
slightly soluble | [Sensitive ]
Hygroscopic | [λmax]
300nm(CH3CN)(lit.) | [Detection Methods]
HPLC,NMR | [Merck ]
14,3348 | [BRN ]
113176 | [InChIKey]
MWVTWFVJZLCBMC-UHFFFAOYSA-N | [CAS DataBase Reference]
553-26-4(CAS DataBase Reference) | [NIST Chemistry Reference]
| [EPA Substance Registry System]
553-26-4(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 ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 2811 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
DW1760000
| [Hazard Note ]
Irritant | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29333999 | [Toxicity]
LD50 orally in Rabbit: 172 mg/kg |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Isoalantolactone-->4,4'-BIPYRIDINE 1,1'-DIOXIDE-->sodium pyridine-4-sulfinate-->4-chloropyridine-->4-Chloropyridinium chloride-->1,4-Benzenediacetic acid, 2-nitro--->Benzoylcholine Chloride-->4-Methyl-2-nitrobenzaldehyde | [Preparation Products]
1-METHYL-[4,4']BIPIPERIDINYL-->Paraquat dichloride-->2,2'-DICHLORO-[4,4']-BIPYRIDINE-->[4,4''-Bipyridine]-2,2''-diamine-->1,1''-[1,2-PHENYLENEBIS(METHYLENE)]BIS-4,4'-BIPYRIDINIUM BISHEXAFLUOROPHOSPHATE-->1,1'-Bis[3-(trimethylammonio)propyl]-4,4'-bipyridinium Tetrachloride Dihydrate |
| Hazard Information | Back Directory | [Chemical Properties]
off-white to tan powder | [Uses]
4,4'-Bipyridine is used in transition-metal complex catalyst chemistry for uniform polymerization, in luminescence chemistry and in spectrophotometric analysis. It plays an important role as a photosensitizer and luminescent material. It is also used as a precursor to paraquat viz. N,N'-dimethyl-4,4'-bipyridinium. | [Definition]
ChEBI: A bipyridine in which the two pyridine moieties are linked by a bond between positions C-4 and C-4'. | [Synthesis Reference(s)]
Tetrahedron Letters, 26, p. 1655, 1985 DOI: 10.1016/S0040-4039(00)98576-9 | [General Description]
4,4′-Dipyridyl (BPY) is an organic linker mainly used in the preparation of coordination polymers. It is a pyridine derivative in which pyridyl groups can rotate along the carbon-carbon structure. It can be used as a catalyst for photoelectrochemical reduction. | [Safety Profile]
Poison by ingestion. When heatedto decomposition it emits toxic vapors of NOx. | [Purification Methods]
It crystallises from water, *benzene/pet ether, ethyl acetate and sublimes in vacuo at 70o. Also purify it by dissolving in 0.1M H2SO4 and twice precipitating by addition of 1M NaOH to pH 8. Then recrystallise it from EtOH. For the dihydrochloride see Viologen below. [Collman et al. J Am Chem Soc 109 4606 1987, Beilstein 23 H 800, 23 III/IV 1371, 23/8 V 28.] |
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