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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

Quality Level

100

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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

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)
Bipyridyl substituted triazoles as hole-blocking and electron-transporting materials for organic light-emitting devices.
Ichikawa M, et al.
Organic Electronics, 9(1), 77-84 (2008)
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)
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