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

Description

4'-Chloro-2,2':6',2''-terpyridine (4'-Cltpy, Cltpy, Cl-terpy) is a tridentate ligand that features a terpyridine (tpy) site with a chlorine atom at the 4'-position. This brown crystalline powder is known for its ability to coordinate with various metal ions through its terpyridine and chlorine sites, leading to the formation of diverse coordination polymers. Crystal structure studies reveal that the terpyridine unit of Cltpy adopts a trans, trans conformation, and molecules self-assemble into stacked columns along the b axis with an inter-planar distance of 3.51 ?. It is also capable of undergoing Williamson type ether reactions with α,ω-bishydroxy-functionalized poly(propylene oxide) and α-hydroxy-ω-carboxy-functionalized poly(ethylene oxide) to produce monoterpyridine terminated telechelics.

Uses

Used in Supramolecular Chemistry:
4'-Chloro-2,2':6',2''-terpyridine is used as a key component in the synthesis of various supramolecular structures, such as double helicates, dendrimers, micelles, and metallo-supramolecular polymers. Its ability to coordinate with metal ions and participate in self-assembly processes makes it a valuable asset in this field.
Used in Monoand Bis-terpyridine Synthesis:
4'-CHLORO-2,2':6',2''-TERPYRIDINE serves as a precursor in the synthesis of monoand bis-terpyridines, which are important building blocks for the development of new supramolecular systems and coordination polymers.
Used in Williamson Type Ether Reactions:
4'-Chloro-2,2':6',2''-terpyridine is utilized in Williamson type ether reactions with α,ω-bishydroxy-functionalized poly(propylene oxide), contributing to the creation of novel materials with potential applications in various industries.
Used in Telechelic Synthesis:
In the synthesis of monoterpyridine terminated telechelics through Williamson type reactions with α-hydroxy-ω-carboxy-functionalized poly(ethylene oxide), 4'-chloro-2,2':6',2''-terpyridine plays a crucial role, enabling the development of advanced polymeric materials with specific end-group functionalities.

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 
• 128143-88-4 2,2':6',2''-Terpyridin-4'(1'H)-one 
• 128143-87-3 1,5-bis(2′-pyridyl)pentane-1,3,5-trione 
• 2524-52-9 ethyl-2-picolinate 

Downstream Products

• 150282-05-6 4'-[7-Benzyloxy-4,4-bis-(3-benzyloxy-propyl)-heptyloxy]-[2,2';6',2'']terpyridine 
• 168642-00-0 4-<4'-Oxa-(2,2':6',2''-terpyridinyl)>butanoic acid 
• 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 
• 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 
• 181866-50-2 4′-methoxy-2,2′:6′,2′′-terpyridine 
• 145533-40-0 4'-ethoxy-2,2' : 6',2''-terpyridine 
• 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 
• 897037-23-9 4′?(4?methoxycarbonylphenyl)?2,2′:6′,2″?terpyridine 
• 193944-67-1 4'-azido-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-