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Merck
CN

D216305

2,2′-Bipyridyl

greener alternative

≥99%, powder or crystals, ReagentPlus®

Synonym(s):

2,2′-Bipyridine, 2,2′-Dipyridine, 2,2′-Dipyridyl

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About This Item

Empirical Formula (Hill Notation):
C10H8N2
CAS Number:
366-18-7
Molecular Weight:
156.18
NACRES:
NA.21
PubChem Substance ID:
57654082
UNSPSC Code:
12352100
EC Number:
206-674-4
MDL number:
MFCD00006212
Beilstein/REAXYS Number:
113089

Key Documents

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Product Name

2,2′-Bipyridyl, ReagentPlus®, ≥99%

InChI key

ROFVEXUMMXZLPA-UHFFFAOYSA-N

InChI

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

SMILES string

c1ccc(nc1)-c2ccccn2

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.

sustainability

Greener Alternative Product

bp

273 °C (lit.)

mp

70-73 °C (lit.)

solubility

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

greener alternative category

Aligned

storage temp.

room temp

Quality Level

200

Gene Information

human ... EPHX2(2053), FNTA(2339)
mouse ... Ephx2(13850)

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Application

2,2′-Bipyridyl has been used in:
  • the preparation of fluorescent dyes like products 754730, 544981, 804215.
  • the preparation ofcopper(II)-bipyridine-naringenin complex.
  • the preparation of 2,2′-bipyridyl hydrobromide.
  • as a ligand in the greener oxidation of alcohols under aerobic conditions
  • as a complex with CuBR2 in the green synthesis of propargylamines
  • the synthesis of [Ru(bipy)3]Cl2, a common metal complex with usefulphotochemistry often used in photoredox catalysis as a sensitizer

Biochem/physiol Actions

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

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. It is a bidentate ligand which has been employed transition metal catalysis, aluminum initiated polymerization, and various other inorganic syntheses. This compound adheres to the principles of greener chemistry, ensuring catalytic efficiency. Click here for more information

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Oral

Storage Class

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

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
0000521786
0000521786
WXBF7594V
WXBF7518V
WXBF7359V

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Inhibition of Petunia flower senescence by 2, 2'-bipyridyl.
Knee M.
Postharvest biology and technology, 9(3), 351-360 (1996)
Solvent-Free A3 and KA2 Coupling Reactions with mol ppm Level Loadings of a Polymer-Supported Copper(II)?Bipyridine Complex for Green Synthesis of Propargylamines
Shuo Yan, et al.
ACS sustainable chemistry & engineering, 7 (10), 9097-9102 (2019)
Bromination of 2,2'-bipyridile.
Zdravkov AB and Khimich NN.
Russ. J. Org. Chem., 42(8), 1200-1202 (2006)
Macromolecules, 27, 645-645 (1994)
Tetrahedron Letters, 34, 6219-6219 (1993)
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