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HomeProduct name list4,4'-Bipyridine

4,4'-Bipyridine

Synonym(s):γ,γ′-Dipyridyl;4,4′-Bipyridine;4,4′-Bipyridyl

  • CAS NO.:553-26-4
  • Empirical Formula: C10H8N2
  • Molecular Weight: 156.18
  • MDL number: MFCD00006416
  • EINECS: 209-036-3
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-09-02 18:23:59
4,4'-Bipyridine Structural

What is 4,4'-Bipyridine?

Chemical properties

off-white to tan powder

The Uses of 4,4'-Bipyridine

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.

What are the applications of Application

4,4′-Bipyridyl is used in the preparation of nanostructures

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.]

Properties of 4,4'-Bipyridine

Melting point: 109-112 °C(lit.)
Boiling point: 305 °C(lit.)
Density  1.2814 (rough estimate)
refractive index  1.6057 (estimate)
Flash point: 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
Sensitive  Hygroscopic
λmax 300nm(CH3CN)(lit.)
Merck  14,3348
BRN  113176
Stability: Stable. Incompatible with strong oxidizing agents, strong acids.
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)

Safety information for 4,4'-Bipyridine

Signal word Danger
Pictogram(s)
ghs
Skull and Crossbones
Acute Toxicity
GHS06
GHS Hazard Statements H301:Acute toxicity,oral

Computed Descriptors for 4,4'-Bipyridine

InChIKey MWVTWFVJZLCBMC-UHFFFAOYSA-N

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