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234672

2,2′:6′,2′′-Terpyridine

98%, solid

Synonym(s):

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

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$89.00

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$169.00

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$498.00

$89.00


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About This Item

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

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Product Name

2,2′:6′,2′′-Terpyridine, 98%

InChI key

DRGAZIDRYFYHIJ-UHFFFAOYSA-N

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

SMILES string

c1ccc(nc1)-c2cccc(n2)-c3ccccn3

assay

98%

form

solid

mp

89-91 °C (lit.)

Quality Level

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1 of 4

This Item
494070798533552933
assay

98%

assay

90%

assay

99%

assay

98%

Quality Level

200

Quality Level

100

Quality Level

100

Quality Level

100

form

solid

form

-

form

powder or crystals (anhydrous)

form

-

mp

89-91 °C (lit.)

mp

257-263 °C (lit.)

mp

70-73 °C (lit.)

mp

59-63 °C (lit.)

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.[1]

General description

2,2′:6′,2′′;-Terpyridine is a tridentate ligand[2] that can be prepared in two steps, starting with 2-acetylpyridine.[3] It coordinates with metal centers to form complexes. It is also utilized in the synthesis of chiral derivatives for asymmetric catalysis.[4]

pictograms

Skull and crossbonesCorrosion

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

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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Chiral 2, 2 `-bipyridines, 1, 10-phenanthrolines, and 2, 2 `: 6 `, 2 ``-terpyridines: Syntheses and applications in asymmetric homogeneous catalysis
G Chelucci, et al.
Chemical Reviews, 102, 3129-3170 (2002)
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)
2, 2?: 6?, 2 ?-Terpyridines: From chemical obscurity to common supramolecular motifs
Constable EC
Chemical Society Reviews, 36(2), 246-253 (2007)
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)

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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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