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798533

Sigma-Aldrich

2,2′-Bipyridyl

greener alternative

anhydrous, free-flowing, Redi-Dri™, ReagentPlus®, 99%

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C10H8N2
Número de CAS:
366-18-7
Peso molecular:
156.18
Beilstein/REAXYS Number:
113089
EC Number:
206-674-4
MDL number:
MFCD00006212
UNSPSC Code:
12352100
PubChem Substance ID:
329768657
NACRES:
NA.21

grade

anhydrous

Quality Level

100

product line

ReagentPlus®
Redi-Dri™

assay

99%

form

powder or crystals (anhydrous)

quality

free-flowing

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.)

greener alternative category

Aligned

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

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General description

2,2′-Bipyridyl, is a symmetrical bipyridine commonly used as a neutral ligand for complexation with metal ions. The molecule is planar with trans-conformation and crystallizes in the monoclinic crystal system.
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Application

2,2′-Bipyridyl may be used for the preparation of aldehydes from primary alcohols via aerobic oxidation using CuI/TEMPO (TEMPO = 2,2,6,6-tetramethyl-1-piperidinyloxyl) catalyst system.

Biochem/physiol Actions

Inhibidor de metaloproteasa; agente quelante del hierro de gran afinidad; puede inhibir enzimas que contengan Fe2+ en concentraciones de 10−8 M.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany
Redi-Dri is a trademark of Sigma-Aldrich Co. LLC

Related product

Referencia del producto
Descripción
Precios

D216305

2,2′-Bipyridyl, ReagentPlus®, ≥99%

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_germany

WGK 3

flash_point_f

267.8 °F - closed cup

flash_point_c

131 °C - closed cup

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Certificados de análisis (COA)

Lot/Batch Number
WXBD2205V
WXBC8527V
WXBC7516V
WXBD1517V
WXBD1377V

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The crystal structure of 2, 2'-bipyridine.
Merritt LL and Schroeder E.
Acta Crystallographica, 9(10), 801-804 (1956)
Bipyridine: the most widely used ligand. A review of molecules comprising at least two 2,2'-bipyridine units.
Kaes C, et al.
Chemical Reviews, 100(10), 3553-3590 (2000)
Jessica M Hoover et al.
Nature protocols, 7(6), 1161-1166 (2012-05-29)
This protocol describes a practical laboratory-scale method for aerobic oxidation of primary alcohols to aldehydes, using a chemoselective Cu(I)/TEMPO (TEMPO = 2,2,6,6-tetramethyl-1-piperidinyloxyl) catalyst system. The catalyst is prepared in situ from commercially available reagents, and the reactions are performed in
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Early life-stages of the endangered white sturgeon (Acipenser transmontanus) have been shown to be among the most sensitive fishes to aqueous copper (Cu) exposure. In a recent analogous study, we examined the role of whole-body Cu accumulation and Na homeostasis
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This study describes a series of newly synthesized phosphine/diimine ruthenium complexes containing the lawsone as bioligand with enhanced cytotoxicity against different cancer cells, and apoptosis induction in prostatic cancer cells DU-145. The complexes [Ru(law)(N-N)2]PF6 where N-N is 2,2'-bipyridine (1) or

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