1148-79-4

Basic information

• Product Name: 2,2':6',2''-TERPYRIDINE
• Synonyms: 2,2':6',2''-Terpyridine,97%;2,2′:6′,2′′-Terpyridine ,98%;2,2',2" TERPYRIDINE (Tripyridine, Tripyridyl);´6',2'']Terpyridine;2,2':6',2"-Terpyridine 98%;2,6-BIS(PYRIDIN-2-YL)PYRIDINE;TERPY
• CAS NO: 1148-79-4
• Molecular Formula: C₁₅H₁₁N₃
• Molecular Weight: 233.27
• EINECS: 214-559-5
• Product Categories: Pyrimidines;Achiral Nitrogen;Py-N
• Mol File: 1148-79-4.mol
• Article Data: 26

Chemical Properties

• Melting Point: 90-93 °C
• Boiling Point: 370 °C
• Flash Point: 182.528 °C
• Appearance: Cream to yellow to brown/Crystalline powder
• Density: 1.1901 (rough estimate)
• Refractive Index: 1.5610 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: dioxane: 0.1 g/mL, clear
• PKA: 4.60±0.10(Predicted)
• Water Solubility: 1.472g/L(24.99 oC)
• BRN: 11199
• CAS DataBase Reference: 2,2':6',2''-TERPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2':6',2''-TERPYRIDINE(1148-79-4)
• EPA Substance Registry System: 2,2':6',2''-TERPYRIDINE(1148-79-4)

Safety Data

• Hazard Codes: T+,T
• Statements: 27/28-37/38-41
• Safety Statements: 26-28-36/37/39-45
• RIDADR: UN 2811 6.1/PG 1
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: I
• Hazardous Substances Data: 1148-79-4(Hazardous Substances Data)

Usage

Application in coordination chemistry

As an NNN-tridentate ligand, the 2,2′:6′,2″-terpyridine plays an important role in coordination chemistry. With three coordination sites and low LUMO, terpyridine and its derivatives are one of the typical Pincer ligand and/or non-innocent ligands in transition metal catalysis. Interesting catalytic reactivities have been obtained with these tpy-metal complexes targeting some challenging transformations, such as C–C bond formation and hydrofunctionalization. The 2,2':6':2''-terpyridine ligand has literally shaped the coordination chemistry of transition metal complexes in a plethora of fields.

Description

A case of occupational dermatitis was reported in a chemical technician, with no cross reactivity to pyridine derivatives.

Chemical Properties

Off-white crystal

Uses

2,2';6',2"-terpyridine is widely utilized in the field of supramolecular chemistry, which is used to manufacture the racks, ladders and grids, helicates, catenanes and dendrimers. It plays an important role as a ligand in coordination chemistry. Its complexes are employed in the oxidation of alcohols, the carbonylation of aromatic compounds and as oxygen-binding molecules. Functionalized terpyridine ligands were used in semiconductors and solar panels. It forms chealate complexes with europium(III) and terbium(III), which is used in protein labelling.

Definition

ChEBI: A tridentate heterocyclic ligand that binds metals at three meridional sites giving two adjacent 5-membered MN2C2 chelate rings.

Synthesis Reference(s)

Journal of the American Chemical Society, 103, p. 3585, 1981 DOI: 10.1021/ja00402a062Organic Syntheses, Coll. Vol. 7, p. 476, 1990

General Description

2,2′:6′,2′′;-Terpyridine is a tridentate ligand that can be prepared in two steps starting from 2-acetylpyridine.

Contact allergens

This molecule is a terpyridine with a 4-methyl substitution. A case of occupational dermatitis was reported in a chemical technician with no cross-reactivity to pyridine derivatives.

Purification Methods

Crystallise it from diethyl ether, toluene or from pet ether, then aqueous MeOH, followed by sublimation in a vacuum at 90o. It is used for estimating Ag and Ru. [Kamra et al. Anal Chim Acta 81 177 1976, Beilstein 26 III/IV 258.]

Upstream product

• 694-59-7 pyridine N-oxide 
• 6104-45-6 3-methylpyrimidin-4-one 
• 109-04-6 2-bromo-pyridine 
• 149775-39-3 Ethyl 6-(2,2'-pyridyl) sulfoxide 
• 626-05-1 2,6-Dibromopyridine 
• 13737-05-8 2-trimethylstannylpyridine 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 214215-03-9 3,5-di(pyridin-2-yl)-1,2,4-triazine 
• 1122-62-9 2-acetylpyridine 
• 53710-17-1 2,6-diiodo-pyridine 
• 99-11-6 citrazinic acid 
• 90050-70-7 ethyl 2,6-dibromo-pyridine-4-carboxylate 
• 223463-02-3 2,6-dibromo-4-(hydroxymethyl)pyridine 
• 108295-45-0 4′-formyl-2,2′:6′2″-terpyridine 

Downstream Products

• 85575-96-8 6,6''-diphenyl 2,2',6',2''-terpyridine 
• 78017-86-4 2,2',6',2''-terpyridine-1,1',1''-trioxide 
• 12577-09-2 Ag(2,2',2''-terpyridyl)(triphenylphosphine)ClO₄ 
• 80934-19-6 (2,2':6',2''-terpyridyl)aquachlorotriphenyltin(IV) 
• 935881-23-5 [(2,2':6',2''-terpyridyl)Ag₂(NO₃)2(bis(diphenylphosphino)methane)] 
• 936008-02-5 [Ag₂(NO₃)(P(cyclohexyl)3)2(2,2':6',2''-terpyridyl)][NO₃] 
• 936023-53-9 [Ag(PPh₃)2(2,2':6',2''-terpyridyl)][NO₃] 
• 122822-72-4 trans(P)-{TcCl(PEtPh₂)2(2,2`:6`,2``-terpyridine)}PF<sub>6</sub> 
• 122822-68-8 trans(P)-{TcCl(PMe<sub>2</sub>Ph)2(2,2`:6`,2``-terpyridine)}OSO₂CF₃ 
• 122822-70-2 trans(P)-{TcBr(PMe₂Ph)2(2,2`:6`,2``-terpyridine)}OSO₂CF₃ 
• 154294-07-2 (2,2':6',2''-terpyridine-κ3N,N',N'')bis(triphenylphosphine-κP)copper(I) perchlorate 
• 154294-09-4 (2,2':6',2''-terpyridine-κ3N,N',N'')bis(triphenylphosphine-κP)silver(I) perchlorate 
• 165405-73-2 trans-[Re(NPh)Cl₂(2,2':6',2''-terpyridine)]PF₆ 

Relevant articles and documents

An improved, two-step synthesis of 2,2′:6′,2″-terpyridine

The important tridentate ligand 2,2′:6′,2″-terpyridine has been synthesized in two steps in an overall yield of 47%. The reaction can be scaled up to provide multigram quantitites of the ligand.

New Approaches to the Synthesis of 2,2′: 6′,2″-Terpyridine and Some of Its Derivatives

A new two-step procedure has been developed for the synthesis of 2,2′: 6′,2″-terpyridine and 4′-methylsulfanyl-2,2′: 6′,2″-terpyridine in more than 70% yield on the basis of Potts’ condensation. Efficient methods have been proposed for purification of all condensation products.

Complexing Equilibria and Redox Potentials of the Ag(II)/Ag(I) System in the Presence of 2,2':6',2''-Terpyridine in Water

The conditional protonation constants (μ = 0.1) for 2,2':6',2''-terpyridine, log K1 = 4.93, log K2 = 3.69, were determined by the pH-metric method.The compositions of complexes of Ag2+ and Ag+ ions with 2,2':6',2''-terpyridine (tp) were studied and equilibria of the complex formation process were described.The values of conditional complex formation constants are as follows: for Ag(tp)2+: log β01 = 5.79, log β02 = 9.68, for Ag(tp)22+: log β02 = 25.31, while the conditional constant of the Ag(tp)NO3 precipitate formation is : KSO = 2.45*104.Using coulometric and chronovoltamperometric measurements, the redox systems being formed in the complex solutions of Ag(II) and Ag(I) were determined and described including their formal potentials. - Keywords: Chronovoltammetry; Formal potential; pH-metry; Redox systems with silver ions; Silver complexes

Synthesis, Characterization, and DFT Analysis of Bis-Terpyridyl-Based Molecular Cobalt Complexes

Terpyridine ligands are widely used in chemistry and material sciences owing to their ability to form stable molecular complexes with a large variety of metal ions. In that context, variations of the substituents on the terpyridine ligand allow modulation of the material properties. Applying the Stille cross-coupling reaction, we prepared with good yields a new series of terpyridine ligands possessing quinoline-type moieties in ortho, meta, and para positions and dimethylamino substituents at central or distal positions. The corresponding cobalt(II) complexes were synthesized and fully characterized by elemental analysis, single-crystal X-ray crystallography, mass spectrometry, and UV-vis, 1H NMR, and Fourier transform infrared (FT-IR) spectroscopy as well as by cyclic voltammetry (CV). Density functional theory (DFT) calculations were performed to investigate the electronic structure of all the Co(II) bis-terpyridyl molecular complexes. In this work, we show that terpyridine ligand functionalization allows tuning the redox potentials of the Co(III)/Co(II), Co(II)/Co(I), and Co(I)/Co(I) (tpy)?- couples over a 1 V range.

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A Mitochondrion-Localized Two-Photon Photosensitizer Generating Carbon Radicals Against Hypoxic Tumors

The efficacy of photodynamic therapy is typically reliant on the local concentration and diffusion of oxygen. Due to the hypoxic microenvironment found in solid tumors, oxygen-independent photosensitizers are in great demand for cancer therapy. We herein report an iridium(III) anthraquinone complex as a mitochondrion-localized carbon-radical initiator. Its emission is turned on under hypoxic conditions after reduction by reductase. Furthermore, its two-photon excitation properties (λex=730 nm) are highly desirable for imaging. Upon irradiation, the reduced form of the complex generates carbon radicals, leading to a loss of mitochondrial membrane potential and cell death (IC50light=2.1 μm, IC50dark=58.2 μm, PI=27.7). The efficacy of the complex as a PDT agent was also demonstrated under hypoxic conditions in vivo. To the best of our knowledge, it is the first metal-complex-based theranostic agent which can generate carbon radicals for oxygen-independent two-photon photodynamic therapy.

Method for large-scale production α, α, α .

The invention discloses a method for large-scale production α, α, α . The reaction operation in Step a was as follows: At room temperature 2 - acetyl pyridine was added. Then N mL of N -dimethyl formamide dimethyl acetal and a catalyst are added to the organic solvent, and after the reaction is completed, the reaction solution is poured into an aqueous sodium hydroxide solution, and then the resulting organic phase is washed, dried, concentrated and recrystallized to obtain an intermediate: 1 - (3 - pyridyl) -3 - (dimethylamino) -2 - propylene -1 - ketone. The method disclosed by the invention is easy to implement large-scale production, high in yield, low in cost, simple to operate and mild in reaction condition.

Preparation method for terpyridine pyridinium complex and application thereof in reverse transcriptase inhibition

The invention belongs to the field of research and development of HIV inhibitors, and discloses a preparation method for a terpyridine pyridinium (II) complex and application thereof in HIV reverse transcriptase inhibition. The structure of a cationic moiety of the terpyridine pyridinium (II) complex is as shown in a formula I. A preparation process for the terpyridine pyridinium (II) complex is optimized, the raw material cost is low, and the reaction time is short. The obtained complex is high in purity and yield and has good water solubility and excellent spectral properties. The terpyridine pyridinium (II) complex has the capability of selective binding to a TAR region on HIV RNA, and can block the reverse transcription process of viral RNA by reverse transcriptase and inhibit the replication of viral RNA. The terpyridine pyridinium (II) complex is a highly affinitive HIV RNA selective binding reagent and a highly active HIV reverse transcriptase inhibitor, and is an HIV drug having a great application potential.