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Merck
CN

14453

2,2′-Bipyridyl

≥98.0% (NT)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C10H8N2
CAS Number:
366-18-7
Molecular Weight:
156.18
EC Number:
206-674-4
UNSPSC Code:
12352100
PubChem Substance ID:
329750479
Beilstein/REAXYS Number:
113089
MDL number:
MFCD00006212

Key Documents

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assay

≥98.0% (NT)

bp

273 °C (lit.)

mp

70-73 °C (lit.), ~70 °C

application(s)

vitamins, nutraceuticals, and natural products

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 the complexation with metal ions. The molecule is planar with trans-conformation and crystallizes in the monoclinic crystal system.

Application

2,2′-Bipyridyl has been used in the preparation of:
  • Polyvinylchloride with thioxanthone moieties, which can be employed as photoinitiator in photopolymerization.
  • A novel block polymer that can form polymeric micelles for drug delivery.
  • As a ligand to prepare cyclometalated iridium(III) complexes.

Biochem/physiol Actions

Metalloprotease inhibitor, high-affinity chelator of iron; may inhibit Fe2+ containing enzymes at 10−8 M.

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

WGK 3

flash_point_f

267.8 °F - closed cup

flash_point_c

131 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Regulatory Information

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Nuclear magnetic resonance spectra of 2, 2'-bipyridyl.
Castellano S, et al.
The Journal of Physical Chemistry, 69(12), 4166-4176 (1965)
Novel polymeric micelles for drug delivery: Material characterization and formulation screening.
Janas C, et al.
International Journal of Pharmaceutics, 509(1-2) (2016)
Cyclometalated Iridium (III) Complexes as Photosensitizers for Long-Range Electron Transfer: Occurrence of a Coulomb Barrier.
Hanss D, et al.
European Journal of Inorganic Chemistry, 2009(32), 4850-4859 (2009)
1002. The stability of metal complexes of 1, 10-phenanthroline and its analogues. Part I. 1, 10-Phenanthroline and 2, 2'-bipyridyl.
Irving HMNH and Mellor DH.
Journal of the Chemical Society, 5222-5237 (1962)
Synthesis and characterization of poly (vinylchloride) type macrophotoinitiator comprising side-chain thioxanthone via click chemistry.
Akat H and Ozkan M
Express Polymer Letters, 5(4), 318-326 (2011)
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