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As polar, basic, low-reactive solvent, precursor, and reagent, pyridine finds wide range of applications in pharmaceuticals, agrochemicals and in the manufacture of dyes and rubber. Further it is used in the textile industry to improve network capacity of cotton. Pyridine finds applications in specialty chemical reagents like Cornforth reagent (pyridinium dichromate, PDC), pyridinium chlorochromate (PCC), the Collins reagent (complex of chromium(VI) oxide with pyridine) and the Sarret reagent (complex of chromium(VI) oxide with pyridine). Pyridine is a widely used ligand in coordination chemistry. Pyridine-base adducts like pyridine-borane and pyridine-sulfur trioxide are widely used owing to their superior characteristics in their reactivity and solubility characteristics.
Baumann, M.; Baxendale I. R. An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles. Beilstein J. Org. Chem. 2013, 9, 2265-2319.
Bull, J. A.; Mousseau, J. J.; Pelletier, G.; Charette, A. B. Synthesis of pyridine and dihydropyridine derivatives by regio- and stereoselective addition to N-activated pyridines. Chem. Rev. 2012, 112 (5), 2642-2713.
Widely used as a base and nucleophilic catalyst in acylations, sulfonylations, etc. See also 4-(Dimethylamino)pyridine, A13016.
Reacts with thionyl chloride to give N-(4-pyridyl)pyridinium chloride hydrochloride, a useful intermediate for the preparation of 4-substituted pyridines by nucleophilic displacement. Thus, reaction with sulfite ion gives the sulfonate: Org. Synth. Coll., 5, 977 (1973). Similarly, pyridine can be activated to substitution at the 4-position by reaction with Ethyl chloroformate, L06311, or tert-Butyldimethylsilyl trifluoromethanesulfonate, A12174. The acyl or silyl pyridinium salt then reacts with Grignards or organocuprates, to give 4-substituted dihydropyridines which can readily be rearomatized: Bull. Chem. Soc. Jpn., 57, 1994 (1984).
For use in Cr(VI) oxidation reactions, see Chromium(VI) oxide, 12522.
Hazard Statements: H225-H302-H312-H332
Highly flammable liquid and vapour. Harmful if swallowed. Harmful in contact with skin. Harmful if inhaled.
Precautionary Statements: P210-P261-P280-P303+P361+P353-P304+P340-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Dispose of contents/container in accordance with local/regional/national/international regulations.