D216305

Sigma-Aldrich

2,2′-Bipyridyl

greener alternative

ReagentPlus®, ≥99%

Sinónimos:
2,2′-Dipyridyl, 2,2′-Dipyridine, 2,2′-Bipyridine
Empirical Formula (Hill Notation):
C10H8N2
Número de CAS:
Peso molecular:
156.18
Beilstein/REAXYS Number:
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

signalword

Danger

hazcat

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 Germany

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

Certificado de Análisis

Certificado de origen

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)
Macromolecules, 27, 645-645 (1994)
Coordination Chemistry Reviews, 93, 205-205 (1989)
Júlio César Conceição Filho et al.
PloS one, 9(9), e107058-e107058 (2014-09-06)
Cancer is the second leading cause of death worldwide and there is epidemiological evidence that demonstrates this tendency is emerging. Naringenin (NGEN) is a trihydroxyflavanone that shows various biological effects such as antioxidant, anticancer, anti-inflammatory, and antiviral activities. It belongs...
Artículos
Tools and techniques for performing atom transfer radical polymerization (ATRP) with benefits and limitations.
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