3-Pyridinecarboxaldehyde

Description

Pyridine-3-carbaldehyde, also known as nicotinaldehyde or 3-Pyridinecarboxaldehyde, belongs to the class of organic compounds known as pyridine carboxaldehydes. These are aromatic compounds containing a pyridine ring which bears a carboxaldehyde group. 3-pyridinecarboxaldehyde is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Pyridine-3-carbaldehyde, an aldehyde containing a nitrogen atom, reacts faster than benzaldehyde with diethylzinc to afford enantioenriched 3-pyridyl alkanol in a reaction in which the same chiral catalyst, i.e., (1S,2R)-N, N-dibutylnorephedrine, is used.

Chemical properties

clear yellow to light brown liquid

The Uses of 3-Pyridinecarboxaldehyde

3-Pyridinecarboxaldehyde is a substituted pyridine with niacin activity. 3-Pyridinecarboxaldehyde is a component of tobacco smoke.

Definition

ChEBI: A pyridinecarbaldehyde that is pyridine substituted by a formyl group at position 3.

Synthesis Reference(s)

Synthetic Communications, 21, p. 1777, 1991 DOI: 10.1080/00397919108021576
Tetrahedron, 32, p. 2549, 1976 DOI: 10.1016/0040-4020(76)88025-8
Tetrahedron Letters, 35, p. 8019, 1994 DOI: 10.1016/0040-4039(94)80038-3

Preparation

3-Pyridinecarboxaldehyde can be produced from nicotinonitrile. Alternatively, it arises by the aerobic oxidation of the corresponding alcohol.

Hazards

3-Pyridinecarboxaldehyde is a severe skin irritant.

Purification Methods

Purified as for pyridine-2-aldehyde. [Beilstein 21 I 288, 21 III/IV 3517, 21/7 V 334.]