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D216305 Sigma-Aldrich

2,2′-Bipyridyl

Green Alternative

ReagentPlus®, ≥99%

Synonym: 2,2′-Bipyridine, 2,2′-Dipyridine, 2,2′-Dipyridyl

  • CAS Number 366-18-7

  • Empirical Formula (Hill Notation) C10H8N2

  • Molecular Weight 156.18

  •  Beilstein/REAXYS Number 113089

  •  EC Number 206-674-4

  •  MDL number MFCD00006212

  •  PubChem Substance ID 57654082

  •  NACRES NA.21

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Properties

Related Categories 12 Principles Aligned Products, ATRP, ATRP Ligands, Biochemicals and Reagents, Broad Spectrum Inhibitors of Proteolytic Enzyme Classes,
Quality Level   200
biological source   synthetic (organic)
grade   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   human ... EPHX2(2053), FNTA(2339)
mouse ... Ephx2(13850)

Description

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

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

1 kg in poly bottle

2.5, 10 g in glass bottle

12 kg in poly drum

25, 100, 500 g 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

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
WGK 3
RTECS 
DW1750000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Atom Transfer Radical Polymerization Tools & Techniques

Controlled radical polymerization (CRP) techniques have been reviewed in a number of articles1,2 and books,3 and include nitroxide-mediated polymerization (NMP),4-7 reversible addition fragmentation ...
Sebastian Grajales, Ph.D.
MilliporeSigma, 6000 N. Teutonia Ave. Milwaukee, WI 53209.
Keywords: Ligands, Polymerization reactions, Purification, Radical polymerization, Reversible addition-fragmentation chain transfer polymerizations, Solution polymerization

Peer-Reviewed Papers
15

References

Related Products

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Description

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902810 4,4′-Bis(trifluoromethyl)-2,⋅2′-bipyridine

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