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D216305

Sigma-Aldrich

2,2′-Bipyridyl

greener alternative

ReagentPlus®, ≥99%

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
Beilstein:
113089
EC Number:
206-674-4
MDL number:
MFCD00006212
UNSPSC Code:
12352100
PubChem Substance ID:
57654082
NACRES:
NA.21

biological source

synthetic (organic)

Quality Level

200

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

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

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

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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. 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

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.

Legal Information

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

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301 + H311

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Oral

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Tetrahedron Letters, 34, 6219-6219 (1993)
Macromolecules, 27, 645-645 (1994)
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)
Coordination Chemistry Reviews, 93, 205-205 (1989)
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