5-Bromo-2-methylpyridine

Description

It is an important intermediate in the organic synthesis, which has many applications, such as pharmaceutical intermediate, organic synthesis, organic solvent, production of dyes, pesticide, and spice. Specifically, this chemical can act as the raw material to prepare 2:2’-dipyridyl and its derivatives.¹ Moreover, this compound may be involved in the synthesis of biaryls through a one-pot tandem borylation/Suzuki-Miyaura cross-coupling reaction catalyzed by a palladacycle.² In addition, 5-bromo-2-methylpyridine has been demonstrated to function as the substrate in a general palladium-catalyzed coupling of aryl bromides/triflates and thiols.³ Besides, this substance can facilitate the synthesis of 5-arylamino-2-picolines via displacement of bromide by anthranilic acid and decarboxylation.⁴

Referrence

1. Willink, H. D. T.; Wibaut, J. P., The preparation of 2 : 2'-dipyridyl and some of its derivatives. Recueil Des Travaux Chimiques Des Pays-Bas 1935, 54, 275-283.
2. Wang, L. H.; Cui, X. L.; Li, J. Y.; Wu, Y. S.; Zhu, Z. W.; Wu, Y. J., Synthesis of Biaryls through a One-Pot Tandem Borylation/Suzuki-Miyaura Cross-Coupling Reaction Catalyzed by a Palladacycle. Eur. J. Org. Chem. 2012, 595-603.
3. Itoh, T.; Mase, T., A general palladium-catalyzed coupling of aryl bromides/triflates and thiols. Org. Lett. 2004, 6, 4587-4590.
4. Louis H. Peterson; Tolman, R. L., Reinvestigation of the synthesis of 5-arylamino-2-picolines J. Heterocycl. Chem. 1977.

Chemical Properties

Light yellow Cryst

Uses

5-Bromo-2-picoline is a halogenated pyridine derivative used is a building block in the preparation of nitrogen containing heterocyclic compounds.