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D216305

Sigma-Aldrich

2,2′-Bipyridyl

greener alternative

ReagentPlus®, ≥99%

Synonym(s):
2,2′-Dipyridyl, 2,2′-Dipyridine, 2,2′-Bipyridine
Empirical Formula (Hill Notation):
C10H8N2
CAS Number:
Molecular Weight:
156.18
Beilstein:
113089
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.21

Quality Level

biological source

synthetic (organic)

product line

ReagentPlus®

assay

≥99%

form

powder or crystals
powder or granules

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

bp

273 °C (lit.)

mp

70-73 °C (lit.)

solubility

ethanol: 100 mg/mL, clear, colorless to faintly yellow

storage temp.

room temp

SMILES string

c1ccc(nc1)-c2ccccn2

InChI

1S/C10H8N2/c1-3-7-11-9(5-1)10-6-2-4-8-12-10/h1-8H

InChI key

ROFVEXUMMXZLPA-UHFFFAOYSA-N

Gene Information

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General description

2,2′-Bipyridyl also known as 2,2′-bipyridine, is a symmetrical bipyridine commonly used as a neutral ligand for chelating with metal ions. A study of its impact on Petunia hybrida flowers showed that it caused inhibition of senescence.
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Application

Ligand for copper in greener oxidation of alcohols under aerobic conditions.
2,2′-Bipyridyl has been used in the preparation of copper(II)-bipyridine-naringenin complex. It may be used in the preparation of 2,2′-bipyridyl hydrobromide.
Bidentate ligand employed in transition metal catalysis and aluminum initiated polymerization (inorganic syntheses).
Ligand for copper in greener oxidation of alcohols under aerobic conditions.

Copper(I)/TEMPO-catalyzed aerobic oxidation of primary alcohols to aldehydes with ambient air

Packaging

25, 100, 500 g in poly bottle
2.5, 10 g in glass bottle
12 kg in poly drum
1 kg in poly bottle

Biochem/physiol Actions

Metalloprotease inhibitor, high-affinity chelator of iron; may inhibit Fe2+ containing enzymes at 10−8 M.

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

267.8 °F - closed cup

Flash Point(C)

131 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Macromolecules, 27, 645-645 (1994)
Bromination of 2,2'-bipyridile.
Zdravkov AB and Khimich NN.
Russ. J. Org. Chem., 42(8), 1200-1202 (2006)
Inhibition of Petunia flower senescence by 2, 2'-bipyridyl.
Knee M.
Postharvest biology and technology, 9(3), 351-360 (1996)
Coordination Chemistry Reviews, 93, 205-205 (1989)
Tetrahedron Letters, 34, 6219-6219 (1993)

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