2,6-Lutidine
2,6-Lutidine
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2,6-Lutidine

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1562440

2,6-Lutidine

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2,6-Lutidine

2,6-Lutidine is a natural heterocyclic aromatic organic compound with the formula (CH3)2C5H3N. It is one of several dimethyl-substituted derivative of pyridine, all of which are referred to as lutidines. It is a colorless liquid with mildly basic properties and a pungent, noxious odor.

It was first isolated from the basic fraction of coal tar and from bone oil.

A laboratory route involves condensation of ethyl acetoacetate, formaldehyde, and an ammonia source to give a bis(carboxy ester) of a 2,6-dimethyl-1,4-dihydropyridine, which, after hydrolysis, undergoes decarboxylation.

It is produced industrially by the reaction of formaldehyde, acetone, and ammonia.

2,6-Lutidine has been evaluated for use as a food additive owing to its nutty aroma when present in solution at very low concentrations.

Due to the steric effects of the two methyl groups, 2,6-lutidine is less nucleophilic than pyridine. Protonation of lutidine gives lutidinium, [(CH3)2C5H3NH]+, salts of which are sometimes used as a weak acid because the conjugate base (2,6-lutidine) is so weakly coordinating. In a similar implementation, 2,6-lutidine is thus sometimes used in organic synthesis as a sterically hindered mild base. One of the most common uses for 2,6-lutidine is as a non-nucleophilic base in organic synthesis. It takes part in the formation of silyl ethers as shown in multiple studies.

Oxidation of 2,6-lutidine with air gives 2,6-diformylpyridine:

2,6-Lutidine also finds application in the synthesis of Nifurpirinol [13411-16-0].

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