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2,2':6',2''-Terpyridine, also known as terpyridine, is a tridentate heterocyclic ligand that can be prepared in two steps starting from 2-acetylpyridine. It is an off-white crystalline compound that binds metals at three meridional sites, giving two adjacent 5-membered MN2C2 chelate rings. Terpyridine plays a significant role in various applications due to its unique chemical properties and ability to form complexes with metals.

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  • 1148-79-4 Structure
  • Basic information

    1. Product Name: 2,2':6',2''-TERPYRIDINE
    2. 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
    3. CAS NO:1148-79-4
    4. Molecular Formula: C15H11N3
    5. Molecular Weight: 233.27
    6. EINECS: 214-559-5
    7. Product Categories: Pyrimidines;Achiral Nitrogen;Py-N
    8. Mol File: 1148-79-4.mol
  • Chemical Properties

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

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

1148-79-4 Usage

Uses

Used in Supramolecular Chemistry:
2,2':6',2''-Terpyridine is used as a building block for creating complex structures such as racks, ladders, and grids, helicates, catenanes, and dendrimers in the field of supramolecular chemistry. Its ability to form stable complexes with metals makes it a versatile component in designing and constructing intricate molecular architectures.
Used in Coordination Chemistry:
In coordination chemistry, 2,2':6',2''-Terpyridine serves as an essential ligand, forming chelate complexes with various metal ions. These complexes are employed in catalytic reactions, such as the oxidation of alcohols and the carbonylation of aromatic compounds, as well as in the development of oxygen-binding molecules.
Used in Semiconductors and Solar Panels:
Functionalized terpyridine ligands are utilized in the development of semiconductors and solar panels, where their ability to form complexes with metals contributes to the enhancement of the electronic properties and overall performance of these devices.
Used in Protein Labelling:
2,2':6',2''-Terpyridine forms chelate complexes with europium(III) and terbium(III), which are used in protein labelling. The unique optical properties of these complexes make them suitable for various applications in bioimaging and sensing.

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.

Synthesis Reference(s)

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

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.]

Check Digit Verification of cas no

The CAS Registry Mumber 1148-79-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,1,4 and 8 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 1148-79:
(6*1)+(5*1)+(4*4)+(3*8)+(2*7)+(1*9)=74
74 % 10 = 4
So 1148-79-4 is a valid CAS Registry Number.

1148-79-4 Well-known Company Product Price

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  • TCI America

  • (T0024)  2,2':6',2''-Terpyridine  >98.0%(GC)(T)

  • 1148-79-4

  • 200mg

  • 490.00CNY

  • Detail
  • TCI America

  • (T0024)  2,2':6',2''-Terpyridine  >98.0%(GC)(T)

  • 1148-79-4

  • 1g

  • 1,150.00CNY

  • Detail
  • Alfa Aesar

  • (A17750)  2,2':6',2''-Terpyridine, 97%   

  • 1148-79-4

  • 0.25g

  • 637.0CNY

  • Detail
  • Alfa Aesar

  • (A17750)  2,2':6',2''-Terpyridine, 97%   

  • 1148-79-4

  • 1g

  • 1096.0CNY

  • Detail
  • Alfa Aesar

  • (A17750)  2,2':6',2''-Terpyridine, 97%   

  • 1148-79-4

  • 5g

  • 4875.0CNY

  • Detail
  • Sigma-Aldrich

  • (86490)  2,2′:6′,2′′-Terpyridine  for spectrophotometric det. of Ag, Fe, Ru, ≥98.5%

  • 1148-79-4

  • 86490-250MG

  • 519.48CNY

  • Detail
  • Sigma-Aldrich

  • (86490)  2,2′:6′,2′′-Terpyridine  for spectrophotometric det. of Ag, Fe, Ru, ≥98.5%

  • 1148-79-4

  • 86490-1G

  • 1,528.02CNY

  • Detail

1148-79-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,2':6',2''-terpyridine

1.2 Other means of identification

Product number -
Other names 2,2′﹕6′,2′′-Terpyridine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1148-79-4 SDS

1148-79-4Relevant articles and documents

Isolation and X-Ray Crystal Structure of a Novel Dihydroterpyridine Dimer formed via an Anionic Cycloaddition

Newkome, George R.,Hager, David C.,Fronczek, Frank R.

, p. 858 - 859 (1981)

The identity of a novel dimer (2), isolated as a by-product from the reaction of 2-lithiopyridine with 2,2'-bipyridine, has been assigned on the basis of X-ray crystal structure analysis.

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

Jameson, Donald L.,Guise, Lisa E.

, p. 1999 - 2002 (1991)

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.

A new approach to symmetric 2,2':6',2'-terpyridines

Adrian Jr., James C.,Hassib, Lamyaa,De Kimpe, Norbert,Keppens, Marian

, p. 2365 - 2370 (1998)

A novel four step process for the preparation of symmetric terpyridines is presented. The title compound, 2,2':6',2'-terpyridine (1a) and a substituted derivative, 5,5'-dimethyl-2,2':6',2'-terpyridine (1b) are prepared. Both 1a and 1b share a common precursor, 2,6-diacetylpyridine (2) and are prepared in overall yields of 73 and 93% respectively. The purities of the crude terpyridine products are in the 90-95% range.

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

Zamalyutin,Bezdenezhnykh,Nichugovskiy,Flid

, p. 419 - 425 (2018)

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.

Syntheses, crystal structures, luminescence and thermal properties of three lanthanide complexes with 2-bromine-5-methoxybenzoate and 2,2:6′,2″-terpyridine

Zhao, Qing-Qing,Ren, Ning,Zhang, Jian-Jun

, p. 1 - 5 (2018)

Three new mononuclear lanthanide complexes [Ln(2-Br-5-MOBA)3(terpy)(H2O)] (Ln = Gd (1), Tb (2), Er (3); 2-Br-5-MOBA = 2-bromine-5-methoxybenzoate; terpy = 2,2:6′,2″-terpyridine) have been successfully synthesized and characterized by single-crystal X-ray diffraction. The complexes 1–3 were isostructural and eight-coordinated, which is different from the binuclear structure of the previously reported complexes. The molecular structure of complexes 1–3 is very interesting: two adjacent mononuclear units are connected through hydrogen bonding giving rise to a pseudo binuclear structure. These pseudo binuclear units are further linked via O–H?Br hydrogen bonds and slightly offset π–π stacking interactions to from 1D and 2D supramolecular structures. The thermal decomposition mechanism of complexes 1–3 was studied by TG analysis and further authenticated by TG/DSC-FTIR techniques. The solid-state luminescent property of complex 2 was investigated at room temperature. The result indicates that Tb (III) complex appear to be promising candidate for the application as green luminescent material.

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

Ignaczak, Maksymilian,Grzejdziak, Andrzej,Olejniczak, Barbara

, p. 515 - 528 (1989)

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

Studies on organometallic compounds. IX. Synthesis of bipyridine N-oxides and terpyridines by palladium catalyzed cross-coupling reaction of trimethylstannylpyridines with bromopyridines

Yamamoto, Yutaka,Tanaka, Takuo,Yagi, Masayoshi,Inamoto, Masayuki

, p. 189 - 194 (1996)

Reaction of trimethylstannylpyridines with bromopyridines in the presence of Pd(PPh3)4 directed toward a practical use was accomplished, giving all nine pyridinylpyridine N-oxides in satisfactory yields. Similarly, nicotelline and 2,2′:6′,2″-terpyridine were produced in good yields.

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

Aroua, Safwan,Todorova, Tanya K.,Hommes, Paul,Chamoreau, Lise-Marie,Reissig, Hans-Ulrich,Mougel, Victor,Fontecave, Marc

, p. 5930 - 5940 (2017)

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.

A new and simple 'LEGO' system for the synthesis of 2,6-oligopyridines

Pabst, Gunther R.,Sauer, Juergen

, p. 6687 - 6690 (1998)

The condensation of α-arylglyoxals with carboxamidrazones 1 - 2 is the best method for the synthesis of aryl or hetaryl substituted 1,2,4-triazines 3 - 4. These 1,2,4-triazines can be easily transformed to pyridines by [4+2] cycloaddition with bicyclo[2.2.1]hepta-2,5-diene followed by [4+2] cycloreversions of nitrogen and cyclopentadiene. This reaction sequence offers a new, simple and general access to 2,6-oligopyridines 8 - 11.

Convenient one-pot procedures for the synthesis of 2,2′:6′, 2″-terpyridine

Cooke, Michael W.,Wang, Jianhua,Theobald, Isabelle,Hanan, Garry S.

, p. 1721 - 1726 (2006)

One-pot reactions to produce 2,2′:6′,2″-terpyridine (tpy) under mild conditions are described under both solventless and solvent-assisted conditions. Tpy can be obtained in 32% yield in a simple one-pot reaction, which can readily be scaled-up to give large quantities of tpy. These new approaches are superior to those previously described because of the fast and efficient synthesis and purification of tpy. Copyright Taylor & Francis Group, LLC.

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