NH2CH2CH2CH2CHO

NH2CH2CH2CH2CHO, also known as 4-aminobutanal or gamma-aminobutyraldehyde, is a small bifunctional organic compound that contains a primary amine and an aldehyde on a four-carbon backbone. Its molecular formula is C4H9NO and its nominal molar mass is about 87.12 g/mol. The molecule features an aldehyde group at one end and an amino group at the other, giving it both nucleophilic and electrophilic character.

Because of its dual functionality, 4-aminobutanal is a versatile building block in organic synthesis. The aldehyde group can participate in typical carbonyl reactions such as nucleophilic additions, condensations, and oxidation to the corresponding carboxylic acid. The primary amine can undergo acylation, alkylation, and formation of imines with carbonyl compounds. Oxidation of the aldehyde yields 4-aminobutanoic acid (gamma-aminobutyric acid, GABA), a naturally occurring compound related to neurotransmission. Reduction of the aldehyde produces 4-aminobutanol derivatives.

In practical use, 4-aminobutanal serves as a precursor for the preparation of aminoalkylated products, gamma- and beta-aminated scaffolds, and various heterocycles. It can be prepared by oxidation of related 4-aminobutanols or by other synthetic routes that introduce the terminal aldehyde functionality.

Safety considerations are typical of small aldehydes and amines: the compound can be irritating to skin and eyes and may cause respiratory and other health hazards if inhaled or ingested. It should be handled in a well-ventilated laboratory with appropriate protective equipment, away from oxidizing agents and moisture.