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234672

Sigma-Aldrich

2,2′:6′,2′′-Terpyridine

98%

Synonym(s):

α,α′,α″-Tripyridyl, 2,6-Di(2-pyridyl)pyridine

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About This Item

Empirical Formula (Hill Notation):
C15H11N3
CAS Number:
1148-79-4
Molecular Weight:
233.27
Beilstein/REAXYS Number:
11199
EC Number:
214-559-5
MDL number:
MFCD00006213
UNSPSC Code:
12352100
PubChem Substance ID:
57648035
NACRES:
NA.21

Quality Level

200

assay

98%

form

solid

mp

89-91 °C (lit.)

SMILES string

c1ccc(nc1)-c2cccc(n2)-c3ccccn3

InChI

1S/C15H11N3/c1-3-10-16-12(6-1)14-8-5-9-15(18-14)13-7-2-4-11-17-13/h1-11H

InChI key

DRGAZIDRYFYHIJ-UHFFFAOYSA-N

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General description

2,2′:6′,2′′;-Terpyridine is a tridentate ligand that can be prepared in two steps, starting with 2-acetylpyridine. It coordinates with metal centers to form complexes. It is also utilized in the synthesis of chiral derivatives for asymmetric catalysis.

Application

Due to the presence of three near-coplanar nitrogen donor atoms, 2,2′:6′,2′′;-terpyridine may be used as a metal-binding domain to form metallo-supramolecular structures.

pictograms

CorrosionSkull and crossbones
GHS05,GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 1 Oral - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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2, 2?: 6?, 2 ?-Terpyridines: From chemical obscurity to common supramolecular motifs
Constable EC
Chemical Society Reviews, 36(2), 246-253 (2007)
An improved, two-step synthesis of 2, 2?: 6?, 2 ?-terpyridine
Jameson DL & Guise LE
Tetrahedron Letters, 32(18), 1999-2002 (1991)
2, 2': 6', 2'-Terpyridine.
Potts KT, et al.
Organic Syntheses, 189-189 (1986)
Complexes of the Ruthenium (II)-2, 2': 6', 2''-terpyridine Family. Effect of Electron-Accepting and-Donating Substituents on the Photophysical and Electrochemical Properties.
Maestri M, et al.
Inorganic Chemistry, 34(10), 2759-2767 (1955)
New functional polymers and materials based on 2, 2': 6', 2 ?-terpyridine metal complexes.
Andres PR and Schubert US.
Advanced Materials, 16(13), 1043-1068 (2004)
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