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| | 4,4'-Bipyridine Basic information |
| | 4,4'-Bipyridine Chemical Properties |
| 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 | | Water Solubility | slightly soluble | | λmax | 300nm(CH3CN)(lit.) | | Sensitive | Hygroscopic | | Merck | 14,3348 | | BRN | 113176 | | Stability: | Stable. Incompatible with strong oxidizing agents, strong acids. | | InChIKey | MWVTWFVJZLCBMC-UHFFFAOYSA-N | | CAS DataBase Reference | 553-26-4(CAS DataBase Reference) | | NIST Chemistry Reference | 4,4'-Bipyridine(553-26-4) | | EPA Substance Registry System | 4,4'-Bipyridine (553-26-4) |
| Hazard Codes | T,Xi | | Risk Statements | 25-36/37/38-20/21-23/24/25 | | Safety Statements | 26-36/37/39-45 | | 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 |
| | 4,4'-Bipyridine Usage And Synthesis |
| 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.] |
| | 4,4'-Bipyridine Preparation Products And Raw materials |
| 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 |
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