26lutidine

2,6-Lutidine, also known as 2,6-dimethylpyridine, is an aromatic amine in the pyridine family. It consists of a six-membered ring containing one nitrogen atom with methyl groups at the 2- and 6-positions, giving a C7H9N formula. It is one of the lutidine isomers, a group of methyl-substituted pyridines used as bases and non-nucleophilic reagents in organic synthesis.

In terms of physical properties, 2,6-lutidine is a colorless to pale-yellow liquid with a strong, characteristic odor. It is more lipophilic than pyridine and has limited water solubility; it dissolves readily in common organic solvents. It is a relatively weak to moderate base; its conjugate acid (the lutidinium cation) is less basic than many more hindered amines due to the ring structure, yet the presence of two ortho methyl groups makes it appreciably bulky and reduces nucleophilicity, which is advantageous in certain reactions.

Applications include its use as a non-nucleophilic base in acylation, sulfonation, and other carbonyl-activation reactions, where a base is needed but nucleophilicity must be suppressed. It is also employed as a solvent or auxiliary in some catalytic or polymerization processes and is a common reagent in pharmaceutical and fine-chemical synthesis.

Safety and handling: 2,6-lutidine is a hazardous chemical and should be handled in a well-ventilated area, with appropriate PPE. It can cause skin and eye irritation and inhalation may irritate the respiratory tract. It should be stored away from oxidizers and heat sources.

See also: other methylpyridines and lutidine isomers.