Skip to Content
Merck
All Photos(6)

Documents

798533

Sigma-Aldrich

2,2′-Bipyridyl

greener alternative

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

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(6)

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:
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

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

Looking for similar products? Visit Product Comparison Guide

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.
We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information.

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

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
Redi-Dri is a trademark of Sigma-Aldrich Co. LLC

related product

Product No.
Description
Pricing

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301 + H311

Hazard Classifications

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

WGK 3

Flash Point(F)

267.8 °F - closed cup

Flash Point(C)

131 °C - closed cup

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 1

1 of 1

4,4′-Bipyridine for synthesis

Sigma-Aldrich

8.20158

4,4′-Bipyridine

The crystal structure of 2, 2'-bipyridine.
Merritt LL and Schroeder E.
Acta Crystallographica, 9(10), 801-804 (1956)
Kamran Shekh et al.
Comparative biochemistry and physiology. Toxicology & pharmacology : CBP, 231, 108723-108723 (2020-02-12)
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
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
Rone Aparecido De Grandis et al.
Bioorganic chemistry, 85, 455-468 (2019-02-19)
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

Articles

Redi-Dri™ – The World of Free-flowing Hygroscopic Products

Redi-Dri™ prevents hygroscopic powders, such as inorganic salts, from absorbing moisture and forming clumps, leaving the salts free-flowing every time.

Redi-Dri™ – The World of Free-flowing Hygroscopic Products

Redi-Dri™ prevents hygroscopic powders, such as inorganic salts, from absorbing moisture and forming clumps, leaving the salts free-flowing every time.

Redi-Dri™ – The World of Free-flowing Hygroscopic Products

Redi-Dri™ prevents hygroscopic powders, such as inorganic salts, from absorbing moisture and forming clumps, leaving the salts free-flowing every time.

Redi-Dri™ – The World of Free-flowing Hygroscopic Products

Redi-Dri™ prevents hygroscopic powders, such as inorganic salts, from absorbing moisture and forming clumps, leaving the salts free-flowing every time.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service