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798533

Sigma-Aldrich

2,2′-Bipyridyl

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

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C10H8N2
Numéro CAS:
366-18-7
Poids moléculaire :
156.18
Numéro Beilstein :
113089
Numéro CE :
206-674-4
Numéro MDL:
MFCD00006212
Code UNSPSC :
12352100
ID de substance PubChem :
329768657
Nomenclature NACRES :
NA.21

Qualité

anhydrous
free-flowing

Niveau de qualité

100

Gamme de produits

ReagentPlus®
Redi-Dri™

Pureté

99%

Forme

powder or crystals (anhydrous)

Caractéristiques du produit alternatif plus écologique

Catalysis
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sustainability

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Point d'ébullition

273 °C (lit.)

Pf

70-73 °C (lit.)

Autre catégorie plus écologique

Aligned

Chaîne SMILES 

c1ccc(nc1)-c2ccccn2

InChI

1S/C10H8N2/c1-3-7-11-9(5-1)10-6-2-4-8-12-10/h1-8H

Clé InChI

ROFVEXUMMXZLPA-UHFFFAOYSA-N

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Description générale

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.

Actions biochimiques/physiologiques

Inhibiteur des métalloprotéases; chelateur de grande affinité du fer; peut inhiber les enzymes contenant du Fe2+ à 10−8 M.

Informations légales

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

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H301 + H311

Classification des risques

Acute Tox. 3 Dermal - Acute Tox. 3 Oral

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

267.8 °F - closed cup

Point d'éclair (°C)

131 °C - closed cup

Certificats d'analyse (COA)

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The crystal structure of 2, 2'-bipyridine.
Merritt LL and Schroeder E.
Acta Crystallographica, 9(10), 801-804 (1956)
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
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)
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

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