4,4'-Bipyridine

4,4'-Bipyridine
  • CAS No.:553-26-4

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  1. This product is a chemical product/pharmaceutical intermediate. It is not a drug, an active pharmaceutical ingredient (API), or a pharmaceutical-grade material. It has not been granted a drug approval number or a Chemical Drug Substance Approval Notice, has not passed drug-related review and approval, and is not manufactured, tested, or released in accordance with pharmaceutical GMP.
  2. This product is intended solely for non-clinical research, process development, quality studies, further chemical processing, or chemical synthesis. It must not be used in drug-product manufacturing, clinical trials, clinical diagnosis, or administration to humans or animals, or be sold, used as an input, submitted for regulatory filing, or released as an API or pharmaceutical material.
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4,4'-Bipyridine Basic information
Product Name:4,4'-Bipyridine
Synonyms:'LGC' (1608);GAMMA,GAMMA'-DIPYRIDYL;GAMMA,GAMMA-DIPYRIDYL;4, 4'-DIPYRIDINE;4,4'-DIPYRIDYL;4,4-DIPYRIDYL;4,4'-BIPYRIDINE;4,4-BIPYRIDINE
CAS:553-26-4
MF:C10H8N2
MW:156.18
EINECS:209-036-3
Product Categories:Viologens (Photochromic, Related Compounds);Functional Materials;Pyridines;Pyridines derivates;PYRIDINE;Photochromic Compounds;bc0001
Mol File:553-26-4.mol
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
pkapK1:3.17(+2);pK2:4.82(+1) (25°C)
color Off-white to beige
Water Solubility slightly soluble
Sensitive Hygroscopic
λmax300nm(CH3CN)(lit.)
Merck 14,3348
BRN 113176
Stability:Stable. Incompatible with strong oxidizing agents, strong acids.
InChIKeyMWVTWFVJZLCBMC-UHFFFAOYSA-N
CAS DataBase Reference553-26-4(CAS DataBase Reference)
NIST Chemistry Reference4,4'-Bipyridine(553-26-4)
EPA Substance Registry System4,4'-Bipyridine (553-26-4)
Safety Information
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
ToxicityLD50 orally in Rabbit: 172 mg/kg
MSDS Information
ProviderLanguage
4,4'-Dipyridyl English
ACROS English
SigmaAldrich English
ALFA English
4,4'-Bipyridine Usage And Synthesis
Chemical Propertiesoff-white to tan powder
Uses4,4'-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.
DefinitionChEBI: 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 Description4,4′-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 ProfilePoison by ingestion. When heatedto decomposition it emits toxic vapors of NOx.
Purification MethodsIt 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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