2,2':6',2''-Terpyridine
[CAS# 1148-79-4]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Pyridine derivative
• Name: 2,2':6',2''-Terpyridine
• Synonyms: 2,6-dipyridin-2-ylpyridine
• Molecular Formula: C₁₅H₁₁N₃
• Molecular Weight: 233.27
• CAS Registry Number: 1148-79-4
• EC Number: 214-559-5
• SMILES: C1=CC=NC(=C1)C2=NC(=CC=C2)C3=CC=CC=N3

Properties

• Melting point: 92 ºC

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07 Danger
• Hazard Statements: H301-H310-H315-H318-H319-H335
• Precautionary Statements: P261-P262-P264-P264+P265-P270-P271-P280-P301+P316-P302+P352-P304+P340-P305+P351+P338-P305+P354+P338-P316-P317-P319-P321-P330-P332+P317-P337+P317-P361+P364-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	1	H300
Serious eye damage	Eye Dam.	1	H318
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	2	H310
Acute toxicity	Acute Tox.	1	H310
Eye irritation	Eye Irrit.	2	H319

Discovory and Applicatios

2,2':6',2''-Terpyridine, commonly referred to as terpyridine, is an organic compound known for its distinctive structure and versatile applications. This compound features a tridentate ligand consisting of three pyridine rings connected by two bridging carbon atoms. Its molecular formula is C15H11N3, and its chemical structure exhibits a notable arrangement of nitrogen and carbon atoms within the aromatic rings.

The discovery of terpyridine dates back to the early 20th century when it was first synthesized by chemists exploring the chemistry of pyridine derivatives. Terpyridine was recognized for its unique ability to form stable complexes with various metal ions, a property that has since driven its extensive use in coordination chemistry and materials science.

The synthesis of terpyridine typically involves the condensation of 2-acetylpyridine with pyridine derivatives under acidic conditions. This reaction results in the formation of the terpyridine ligand, which can then be further processed or functionalized to meet specific needs in various applications.

One of the primary applications of 2,2':6',2''-terpyridine is in the field of coordination chemistry. Its tridentate nature allows it to form chelate complexes with metal ions, providing stability and specificity in coordination compounds. This property makes terpyridine a valuable ligand in the synthesis of metal-organic frameworks (MOFs) and other coordination complexes used in catalysis and material science. For example, terpyridine-based complexes are used as catalysts in a range of chemical reactions, including oxidation and reduction processes, due to their ability to stabilize reactive intermediates and enhance reaction efficiency.

In the realm of materials science, terpyridine is employed in the development of advanced functional materials. Its coordination capabilities facilitate the design of molecular sensors, where terpyridine-based metal complexes are used to detect specific ions or molecules through changes in optical properties or electronic behavior. Additionally, terpyridine derivatives are incorporated into polymer matrices to create materials with tailored properties, such as enhanced mechanical strength or specific electronic characteristics.

Terpyridine also finds applications in the field of medicinal chemistry. The compound's ability to form stable metal complexes is leveraged in the development of new pharmaceuticals. Metal-terpyridine complexes have been explored for their potential as therapeutic agents, including anticancer drugs, where the metal center plays a crucial role in the drug's biological activity. Research in this area focuses on optimizing the interaction between the terpyridine ligand and metal ions to achieve desired pharmacological effects.

Another significant application of 2,2':6',2''-terpyridine is in the development of optoelectronic devices. The compound's electronic and optical properties are utilized in the creation of light-emitting materials, sensors, and other devices where precise control of electronic states is essential. Terpyridine-based materials have shown promise in improving the performance of organic light-emitting diodes (OLEDs) and photovoltaic cells due to their ability to influence charge transport and light emission.

Overall, 2,2':6',2''-terpyridine is a versatile compound with significant applications in coordination chemistry, materials science, medicinal chemistry, and optoelectronics. Its unique structural features and ability to form stable metal complexes make it a valuable tool in a range of scientific and industrial fields.