128143-89-5

Basic information

• Product Name: 4'-CHLORO-2,2':6',2''-TERPYRIDINE
• Synonyms: 4'-CHLORO-2,2':6',2''-TERPYRIDINE;4'-CHLORO-2,2'6'2''-TERPYRIDINE;4''-CHLORO-2,2'':6'',2''-TERPYRIDINE 99%;4-Chloro-2,6-di(pyridin-2-yl)pyridine ,99%;4'-Chloro-2,2':6',2''-terpyridine,99%;4-Chloro-2,6-di(pyridin-2-yl)pyridine;2,2':6',2''-Terpyridine,4'-chloro-;4'-Chloro-2,2,2':6',2''-terpyridine
• CAS NO: 128143-89-5
• Molecular Formula: C₁₅H₁₀ClN₃
• Molecular Weight: 267.71
• EINECS: -0
• Product Categories: C9 to C46Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyridines;Building Blocks;C13 to C40;C7 to C18;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 128143-89-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 148-150 °C(lit.)
• Boiling Point: 416.73°C (rough estimate)
• Flash Point: 241.2 °C
• Appearance: Brown/Crystalline Powder
• Density: 1.2245 (rough estimate)
• Refractive Index: 1.6010 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 4.22±0.22(Predicted)
• Water Solubility: Slightly soluble in water.
• BRN: 3613386
• CAS DataBase Reference: 4'-CHLORO-2,2':6',2''-TERPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-CHLORO-2,2':6',2''-TERPYRIDINE(128143-89-5)
• EPA Substance Registry System: 4'-CHLORO-2,2':6',2''-TERPYRIDINE(128143-89-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-39
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 128143-89-5(Hazardous Substances Data)

Usage

Chemical Properties

brown crystalline powder

Uses

4'-Chloro-2,2':6',2''-terpyridine is widely utilized in the field of supramolecular chemistry, which is used to manufacture double helicates, dendrimers, micelles and metallo-supramolecular polymers. It is used to synthesize the mono- and bis-terpyridines. It is actively involved in Williamson type ether reactions alpha,μ-bishydroxy-functionalized poly(propylene oxide).

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. Mol-ecules assemble themselves into stacked columns along the b axis, with an inter-planar distance of 3.51?. 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.

Upstream product

• 474745-38-5 2,2':6',2'-terpyridin-4'-(1'H)-one acetic acid adduct 
• 101003-65-0 4'-hydroxy-2,2':6',2''-terpyridine 
• 128143-87-3 1,5-bis(2′-pyridyl)pentane-1,3,5-trione 
• 2524-52-9 ethyl-2-picolinate 
• 128143-88-4 2,2':6',2''-Terpyridin-4'(1'H)-one 

Downstream Products

• 178265-65-1 4′-(4-amino-phenyl)-2,2′:6′,2′′-terpyridine 
• 193944-67-1 4'-azido-2,2':6',2-terpyridine 
• 479200-07-2 ((C₅H₄N)2C₅H₂N(OCH₂CH₂)3OC₆H₄C₅H₃N)2 
• 247594-36-1 1-[(2R,4S,5R)-4-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-([2,2';6',2'']terpyridin-4'-yloxymethyl)-tetrahydro-furan-2-yl]-4-{[bis-(4-methoxy-phenyl)-phenyl-methyl]-amino}-1H-pyrimidin-2-one 
• 181866-50-2 4′-methoxy-2,2′:6′,2′′-terpyridine 
• 145533-40-0 4'-ethoxy-2,2' : 6',2''-terpyridine 
• 222171-12-2 {9-[(2R,3R,4R,5R)-4-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-3-methoxy-5-([2,2';6',2'']terpyridin-4'-yloxymethyl)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-[bis-(4-methoxy-phenyl)-phenyl-methyl]-amine 
• 222171-10-0 {9-[(2R,4S,5R)-4-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-([2,2';6',2'']terpyridin-4'-yloxymethyl)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-[bis-(4-methoxy-phenyl)-phenyl-methyl]-amine 
• 168642-00-0 4-<4'-Oxa-(2,2':6',2''-terpyridinyl)>butanoic acid 
• 150282-05-6 4'-[7-Benzyloxy-4,4-bis-(3-benzyloxy-propyl)-heptyloxy]-[2,2';6',2'']terpyridine 

Relevant articles and documents

Synthesis of substituted terpyridine ligands for use in protein purification

A number of 4,4″-disubstituted terpyridines bearing a 4′-thioethanamine linker, and regioisomers thereof, have been synthesised from 4-substituted picolinates. The substituted terpyridines were immobilised onto epoxy-activated Sepharose FF gel, creating functionalised solid supports for the fractionation of proteins - including antibodies - by mixed mode affinity chromatography. The metal chelating properties of the immobilised ligand render the stationary phase also amenable for use in immobilised metal-ion affinity chromatography (IMAC), and have been demonstrated with the purification of suitably tagged green fluorescent protein (GFP).

Gelation properties of terpyridine gluconic acid derivatives and their reversible stimuli-responsive white light emitting solution

Two gluconic acid derivatives C3 and C6 bearing a terpyridyl moiety were designed and synthesized. Thanks to the hydrophilic interaction from glucosyl moiety, C3 and C6 can dissolve in polar solvents and gel aromatic solvents with a critical gel concentration of weight 1.5%. The solution consisting of organic ligand C3 as sensitizer and Ln(III) ions as emitters can realize white light emission with thermo- and chemical stimuli-response properties in luminescence spectra. Further, the self-assemblies of C3 and C6 were examined by the combination of the theoretical calculations via hybrid density functional theory (DFT) with 1H nuclear magnetic resonance (1HNMR) and powder X-ray diffraction (PXRD) analysis. The study actually provides a reliable method for the formation of potential functional smart materials.

Efficient synthetic approaches to access ruthenium(II) complexes with 2-(Trimethylsilyl)ethyl- or acetyl-protected terpyridine-thiols

A series of thiol-functionalized terpyridines (tpy) with protective groups, such as acetyl (Ac), 2-(trimethylsilyl)ethyl (TMSE), and tert-butyl (tBu), and the corresponding ruthenium(II) complexes were synthesized in high yields. The TMSE-protected thiol-