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405868

Sigma-Aldrich

4′-Chloro-2,2′:6′,2′′-terpyridine

greener alternative

99%

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About This Item

Empirical Formula (Hill Notation):
C15H10ClN3
CAS Number:
Molecular Weight:
267.71
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

99%

greener alternative product score

old score: 51
new score: 35
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greener alternative product characteristics

Waste Prevention
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Greener Alternative Product

mp

148-150 °C (lit.)

greener alternative category

SMILES string

Clc1cc(nc(c1)-c2ccccn2)-c3ccccn3

InChI

1S/C15H10ClN3/c16-11-9-14(12-5-1-3-7-17-12)19-15(10-11)13-6-2-4-8-18-13/h1-10H

InChI key

AHEMFMCEBIJRMU-UHFFFAOYSA-N

General description

4′-Chloro-2,2′:6′,2′′-terpyridine (4′-Cltpy, Cltpy, Cl-terpy) is a tridentate ligand that contains a terpyridine (tpy) site with a Cl site at the 4 -position. It coordinates with various metal ions through these two sites to form different coordination polymers. Crystal structure study shows terpyridine unit of Cltpy adopts a trans, trans conformation. Mol­ecules assemble themselves into stacked columns along the b axis, with an inter­planar distance of 3.51Å. It undergoes Williamson type ether reactions with α,ω-bishydroxy-functionalized poly(propylene oxide). It undergoes Williamson type reaction with α-hydroxy-ω-carboxy-functionalized poly(ethylen-oxide) to afford monoterpyridine terminated telechelics.
We are committed to bringing you Greener Alternative Products, which adhere to one of the four categories of Greener Alternatives . This product belongs to category of Re-engineered products, showing key improvements in Green Chemistry Principles “Waste Prevention”, “Atom Economy”, “Less Hazardous Chemical Syntheses”, “Safer Solvents and Auxiliaries” and “Use of Renewable Feedstock”. Click here to view its DOZN scorecard.

Application

4′-Chloro-2,2′:6′,2′′-terpyridine may be used in the preparation of the following:
  • mono- and bis-terpyridines
  • bis-hydroxy-functionalized terpyridine cadmium(II) complex and a fullerene derivative
  • 4-functionalized 2,2´:6´,2´´-terpyridines, building blocks for novel supramolecular structures, such as double helicates, dendrimers, micelles and metallo-supramolecular polymers

Pictograms

Skull and crossbonesCorrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

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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New 4'-Functionalized 2, 2': 6', 2''-Terpyridines for Applications in Macromolecular Chemistry and Nanoscience.
Andres PR, et al.
European Journal of Organic Chemistry, 2003(19), 3769-3776 (2003)
Access to supramolecular polymers: Large scale synthesis of 4'-chloro-2, 2': 6', 2''-terpyridine and an application to poly (propylene oxide) telechelics.
Schubert US, et al.
Designed Monomers and Polymers, 5(2-3), 211-221 (2002)
Synthesis, Characterization, Crystal Structure, and Biological Studies of a Cadmium (II) Complex with a Tridentate Ligand 4'-Chloro-2,2':6',2''-Terpyridine.
Saghatforoush LA, et al.
Bioinorganic Chemistry and Applications, 2011 (2011)
4'-Chloro-2, 2': 6', 2''-terpyridine.
Beves JE, et al.
Acta Crystallographica Section E, Structure Reports Online, 62(6), o2497-o2498 (2006)
Functionalized oligomers and copolymers with metal complexing segments: a simple and high yield entry towards 2, 2': 6', 2 ?-terpyridine monofunctionalized telechelics.
Schubert US and Eschbaumer C.
Macromolecular Symposia, 163(1) (2001)

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