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552933

Sigma-Aldrich

2,2′-Dipyridyl N-oxide

98%

Synonym(s):

2,2′-Bipyridine 1-oxide, 2,2′-Bipyridine N-oxide, 2,2′-Bipyridine monooxide, 2,2′-Bipyridyl N-oxide, 2,2′-Dipyridyl 1-oxide

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About This Item

Empirical Formula (Hill Notation):
C10H8N2O
CAS Number:
33421-43-1
Molecular Weight:
172.18
MDL number:
MFCD00065168
UNSPSC Code:
12352100
PubChem Substance ID:
24879297
NACRES:
NA.22

assay

98%

mp

59-63 °C (lit.)

SMILES string

[O-][n+]1ccccc1-c2ccccn2

InChI

1S/C10H8N2O/c13-12-8-4-2-6-10(12)9-5-1-3-7-11-9/h1-8H

InChI key

KIKATWFLYDKKOL-UHFFFAOYSA-N

General description

2,2′-Dipyridyl N-oxide is a mono-N-oxide of 2,2′-bipyridine. It is widely used as a chelating agent. 2,2′-Bipyridine N-oxide readily forms complexes with transition metal perchlorates and divalent 3d metal nitrates. It can be prepared from 2,2′-bipyridyl.

Application

2,2′-Dipyridyl N-oxide(Obpy) may be used to synthesize the following:
  • 2,2′-bipyridyl-6-carbonitrile
  • 4-nitro-2,2′-bipyridyl N-oxide by reaction with potassium nitrate in sulfuric acid
  • Eu(TTA)3(Obpy), an electroluminescent red emitter obtained via reaction with europium(III) chloride hexahydrate (EuCl3.6H2O) and 2-thenoyltrifluoroacetonate(TTA)

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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’.

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N*-N*-S* tridentate ligand system as potential antitumor agents.
Antonini I, et al.
Journal of Medicinal Chemistry, 24(10), 1181-1184 (1981)
A high yielding preparation of 2, 2'-bipyridine-1-oxide.
Joachim DFW and Betania D'heni M.
Organic preparations and procedures international, 30(4), 467-469 (1998)
2, 2'-bipyridine n-oxide and 1, 10-phenanthroline n-oxide complexes with divalent 3d metal nitrates.
Speca AN, et al.
J. Inorg. Nucl. Chem., 36(12), 3751-3761 (1974)
2, 2'-Bipyridine N-oxide chelates with divalent 3d metal perchlorates.
Speca AN, et al.
Inorganic Chemistry, 12(6), 1221-1226 (1973)
An efficient electroluminescent (2, 2'-bipyridine mono N-oxide) europium (III) ?-diketonate complex
Zhu H-X, et al.
Journal of Materials Chemistry, 14(18), 2732-2734 (2004)
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