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4,4'-Bipyridine

Basic information Safety Supplier Related

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
  • 553-26-4
Mol File:
553-26-4.mol
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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)
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.
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)
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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
Toxicity
LD50 orally in Rabbit: 172 mg/kg

MSDS

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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

Preparation Products

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