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)

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

• Language:English Provider:4,4'-Dipyridyl
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

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(553-26-4)Related Product Information

• Pyridine
• 4-Aminobutyric acid
• DIPIPERIDINOMETHANE
• Diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate
• Sulfasalazine
• Chromium picolinate
• 2,2'-Bipyridine
• Morfamquat(dichloride((content>65%)
• Paraquat methosulfate
• 2,2':6',2''-TERPYRIDINE
• !2,2'-bipyridine! !dihydrochloride!
• 2,2'-DIPYRIDYL N,N'-DIOXIDE
• tris[2,2'-bipyridine]ruthenium dichloride ,tris(2,2’-bipyridine-n,n’)-,dichloride,(oc-6-11)-ruthenium(2+
• 4,4'-Dinonyl-2,2'-bipyridine
• 4,4’-diphenyl-2’-bipyridin
• Paraquat dichloride
• 4,4'-Dipyridyl hydrate
• ETHYL VIOLOGEN DIPERCHLORATE