The Synthetic Routes of 4′-Chloro-2,2′:6′,2′′-terpyridine

4′-Chloro-2,2′:6′,2′′-terpyridine, also known as TCP, is a widely used intermediate in the chemical industry.
It is used in the production of several important chemicals, including pesticides, pharmaceuticals, and dyes.
The synthesis of TCP has been extensively studied and there are several synthetic routes available.
In this article, we will discuss the most commonly used synthetic routes for the production of 4′-Chloro-2,2′:6′,2′′-terpyridine.

Route 1: via Chlorination of 2,2′:6′,2′′-terpyridine

This is the most commonly used synthetic route for the production of TCP.
The reaction involves the chlorination of 2,2′:6′,2′′-terpyridine using chlorine gas or hydrochloric acid.
The reaction is exothermic and requires careful handling.
The reaction can be carried out in the presence of a solvent such as acetone or dichloromethane.
The product is isolated by precipitation with a mineral acid such as hydrochloric acid.

Route 2: via Reductive Chlorination of Pyridine

This route involves the reduction of pyridine to 2,2′:6′,2′′-terpyridine and its subsequent chlorination.
The reaction is carried out in the presence of a reducing agent such as hydrazine and a chlorinating agent such as bleach.
The product is isolated by precipitation with a mineral acid such as hydrochloric acid.

Route 3: via N-Chlorosuccinimide (NCS)

This route involves the use of N-chlorosuccinimide as a chlorinating agent.
The reaction involves the reaction of N-chlorosuccinimide with 2,2′:6′,2′′-terpyridine in the presence of a solvent such as benzene or toluene.
The product is isolated by filtration and washing with a solvent such as ether.

Route 4: via N-Bromosuccinimide (NBS)

This route involves the use of N-bromosuccinimide as a brominating agent.
The reaction involves the reaction of N-bromosuccinimide with 2,2′:6′,2′′-terpyridine in the presence of a solvent such as benzene or toluene.
The product is isolated by filtration and washing with a solvent such as ether.

Advantages of Synthetic Routes for 4′-Chloro-2,2′:6′,2′′-terpyridine

The synthetic routes for 4′-Chloro-2,2′:6′,2′′-terpyridine have several advantages.
Firstly, they are relatively simple and economical.
Secondly, they are widely used and well-established in the chemical industry.
Thirdly, they provide a reliable source of high-quality TCP, which is used in the production of several important chemicals.

Conclusion

4′-Chloro-2,2′:6′,2′′-terpyridine is an important intermediate in the chemical industry and several synthetic routes are available for its production.
The most commonly used routes include chlorination of 2,2′:6′,2′′-terpyridine, reductive chlorination of pyridine, N-chlorosuccinimide (NCS), and N-bromosuccinimide (NBS).
These routes are simple, economical, and well-established in the industry and provide a reliable source of high-quality TCP.